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14 Dating Lessons From My 14 Months Away

18 Jan

by Cali

My dearest readers, allow me to start with an apology. I realize I am an asshole for unceremoniously disappearing for over a year. I’d love to be able to blame my new job or the challenges I was having with the hosting servers (all true!) BUT the fact of the matter is, I dropped the ball and I’m sorry.

For a while I thought maybe I’d just never write again. I really wasn’t sure where to start after such a long hiatus and I spent much time debating the different ways to catch you all up on DC, Robbie, Mister 2 First Names and D. Ultimately I decided that a good old fashioned list of lessons learned would do the trick. Since this past year was probably the most critical year I’ve had in my long dating career, I am hoping that at least a few of my takeaways may be applicable (or entertaining) to you.

So now, without further ado, here are 14 dating do’s and don’t I’ve learned over the past 14 months.

1. Don’t kid yourself that you’re over someone you once loved after only 2 months. You may have moments of strength or clarity, but actually getting over someone takes much more time and perspective.

2. Do set arbitrary dating goals to get yourself back in the game. During the last week of 2014 I knew I was in a dating funk and wanted to do something about it. I decided to be methodical and declared that I would be going to go on one date a week in 2015.  In order to accomplish this resolution, I immediately began messaging guys I had been ignoring on Tinder and, as it turns out, one of those guys ended up being someone really special.

3. Do go all in on the moment when it feels right. When I first started talking to DC, I was instantly intrigued. We exchanged some high-quality, witty banter over the course of a few days and, before I knew it, he was on his way up to NYC to meet me. 6 hours into our dinner date I was smitten. I found him super attractive, both physically and intellectually, and I was just so thrilled to be feeling something for someone other than Robbie. Soooo, despite my best judgment, I went for it and joined him for champagne, chocolate covered strawberries and more in his suite. And you know what, it was probably one of the best decisions of my life. The months that followed had some pretty incredible highlights and I wouldn’t trade them for the world.

4. Don’t go on a date with your ex- boyfriend an hour before you go on a date with a guy you’re really into. Especially when your ex figures out you’re going on a date after. He will get you drunk, very drunk, and then proceed to text you about how he hopes you think of him when you sleep with the guy your dating. Not exactly the ideal pre date activity. Additionally, don’t go on a first date with a guy directly after spending 24 hours in your ex’s bed.

5. Don’t try to hang out “as friends” with your ex, at his home, while making cocktails. The idea of being friends with your recent ex is laughable enough. But if you ARE going to attempt this, going to his house, alone, is not going to be successful. It’s likely sometime around your second manhattan you’ll both begin talking about your feelings, which will quickly become dramatic and may or may not end in a makeout session and a fight.

5A. (RELATED) Don’t flip your hair and storm out of your exs’ apartment, no matter how crazy he is making you. Perhaps don’t do this at anyone’s apartment, but definitely not your ex’s. It will not result in warm fuzzy feelings OR sex.

6. Don’t hang out with your ex when he’s dating someone else. It may be tempting especially when you still have feelings for said ex and you think his replacement girl is laughable. And you may love hearing how you’re the only one who gets him and how great it is to talk to you blah blah blah… However, if and when you do think about getting back together with him, you’ll never be able to forget how very comfortable he was with kissing you while dating her.

dating lessons7. Do go out of your way to be romantic. When DC came back for a visit on his birthday he told me “not to do anything at all, because spending time with me would be present enough.” And in the past, I would have probably just listened to him as I would have been afraid of fresking him out and coming on too strong when we were just getting to know each other. But I decided to ignore my anxiety and went out and got him a little cake, balloons, a fancy bottle of champagne and confetti – all of which was very well received. :)

8. Don’t hook up with a guy who is staying in the same hotel room as the other guy you just gave your number to. You will not appear classy… however, you will have a good story to tell.

9. Do be more open to second dates. I used to decline a second date if I wasn’t head over heels on the first date, as I didn’t want to waste anyone’s time. But this past year I decided to be more open minded and see where things could go. While none of my second dates ended up being my ideal man, it’s a strategy I feel good about and one I intend to continue.

10. Do know when it’s time to walk away. Sometimes, even if you really, really love someone, you have no choice but to recognize that it just isn’t going to work. No matter how much has changed, or how much potential there may be, you have to listen to your gut when it says it’s over. I clearly spent a lot of time in the past year trying to find a place for Robbie in my life (see above as evidence) but in the end I realized I had tried everything and it just wasn’t meant to be. So I walked away and am proud of myself for finding the strength to cut him out completely and focus on moving on.

11. Do follow your heart, even when you think it might be wrong. I don’t think anyone thought what I was dong with Robbie was smart… He broke my heart once, so why wouldn’t he do it again. But you know what, he didn’t. Yes, it’s true, a lot of my time and energy went into things with him last year. But when it became clear to me that even after everything we had gone through we still weren’t going to work, I was the one to walk away. And while I am of course sad, I mostly just feel good about this decision and grateful for the perspective I now have.

12. Don’t get so stuck on what you think you want, that you miss what’s right in front of you. This is something I’ve been thinking about a lot lately. The last few years have made it really clear to me what I do and don’t want in a partner, and yet sometimes I wonder if all this clarity might be a bad thing. I can’t help but think I could be missing out on something really good just because it doesn’t fit exactly the mold I think I need.

13. Don’t be surprised when you do actually fall out of love with someone. I saw D for the first time in over a year over Christmas break and it was soooo…. awkward. While his feelings have not changed, mine certainly have, and I felt so odd spending time with him. When I looked at him I could remembered the decade I spent crying, hoping and obsessing over him, and yet now I feel literally nothing.  It’s actually laughable to think about the two of us together and I can’t believe how convinced I was that he was the one for me. I very much look forward to the day that I can say the same about Robbie.

14. Don’t waste your time when timing isn’t right. I was HUGELY into Mister 2 First Names (not just due to aforementioned names, although that was part of it). This guy was so incredibly attractive, sarcastic, smart and amazing in bed. In fact, my biggest complaint about him was that he was freakishly perfect, and thus quite intimidating. However, I would have happily gone all in on being intimidated, if he hadn’t told me he was trying to avoid getting into anything serious due to a recent break-up. Seeing as how I have been down that road before and it has gone poorly, I decided to skip it this time around and went on my merry way. That being said, if homeboy ever resurface I will be super pleased, because DAMN.

And there you have it, the 14 dating lessons I learned from my 14 months away. Friends, I promise I won’t be such a stranger and will write again soon.  I’ll have you know that I have been very busily dating in order to provide you with good content, soooo you’re welcome.

Stay tuned…

How to Heal From A Break-Up

2 Nov

Post by Cali

You guys, I am happy to report that I have officially healed from my “break-up” and am actually in a really freaking good place. I am starting to think that maybe the way this relationship ended was the best thing that has ever happened to me because it has completely changed my priorities in dating. And even though it has been less than two months since he and I have talked, I am already feeling fairly certain that there is another great love out there for me and that this time, it’s going to be right.

So, for those of you still trying to figure out how to get over a break-up, here’s what was successful for me:

1. Get your feelings out. Tell a friend, tell your mom, tell a therapist – whomever you’d like – just don’t bottle those bad boys up inside. For me, I think writing my last blog post was fairly crucial in my healing process, as it was shortly thereafter that I began to feel a lot better. There’s so much power in acknowledging how you’re feeling, because once you know exactly what you’re dealing with, you can begin to tackle it.

2. Rebound. It’s possible not everyone agrees with me on this, but I think rebounding was a key step in moving me forward. I met a very nice (British!) guy right as things were beginning to go south with me and Robbie and he has cheered me up considerably over the past 2 months.

The night we met we spent a good chunk of time talking about how fucked up our past/current relationships were (in between convincing the entire bar that we were engaged). I learned that he was only a month out of a toxic relationship and since we were both in similar places, I decided he seemed like an ideal rebound candidate. He was/is.

Over the past two months we’ve been on some lovely dates and have had a lot of fun together. He’s kept me distracted from thinking about Robbie and has crushed any of those, “what if I never meet anyone cool again??” questions that we all ask ourselves when going through a break-up. But best of all, he got me past my hang-up about having sex with someone other than Robbie. I was really dreading that moment, because let’s be real, sex was definitely the healthiest aspect of the Robbie/Cali drama. I knew the first time I slept with someone new it would be weird and sad for me, and thus welcomed the opportunity to get that out of the way with someone I wasn’t planning on building a relationship with.

All in all, spending time with this brit was a great stepping stone and it opened me up to the idea that there may be something else real out there for me – sooner than I thought.

3. Let go of the anger. Even if your anger is completely and totally justified, it will do nothing positive for your life. I’ve made a really conscientious effort to try and put myself in his shoes, and think about how he must be feeling and why he did the things he did. I know in my heart that he’s not a terrible person – just a lost person with a lot of demons. And while I was beyond hurt by how things went down, I forgive him.

Screen Shot 2014-11-02 at 12.55.51 PM4. Keep it classy. When I ran into two of his best friends about a month ago I could have totally gone all, “Carrie And The Post-it Rant at Bed” on them — but I didn’t. Instead, I just said hi and asked them about their lives, etc. I didn’t drop any hints about how I was dating someone new, or make any passive aggressive comments about how their friend had unceremoniously broken my heart (both things I would have definitely done in years past) and I walked away feeling really good about myself.

Similarly, I’ve tried to keep it mellow with passive aggressive comments on Facebook. Since he and I are technically still friends and have so many friends in common, I’ve tried my best to curb my desires to update things that I know will hurt him. That being said, I’m not going to hide the fact that I am happy and dating someone either. There’s a fine line and I think I am doing a reasonably decent job of walking it.

5. Surround yourself with good friends. I cannot express enough how lucky I have been to have so many fun friends to distract me. It’s really hard to lament over the ending of a relationship when you are busy all the time and are surrounded by people who bring out the best in you. It just is as simple as that.

6. Cut the ex out. Everyone tries to skip this step, but it’s probably the most important. I am actually really grateful that Robbie went out the way he did because I have zero interest in ever speaking with him again. I’ve never once been inclined to text him (again, unlike how I’ve behaved in any other break-up) and I am honestly just relieved he’s out of my life.

And it’s not just that we aren’t talking, we’re now (more or less) completely disconnected. One of the best things I did was to unfollow him on Instagram. His profile is private, so now I can’t see what he updates and that’s just fine with me. I’m also lucky that he put me on some sort of setting so that I can’t see what he posts on Facebook…. GREAT! I don’t have any desire to know what he’s up to and it’s really hard to dwell on someone who you know nothing about. (Plus I get just a tiny bit of enjoyment over the fact that the last post I am able to see is a really horrible picture of him. Makes me chuckle every time).

So there you have it. That’s how I’ve gotten over this hurdle of a broken heart and I can tell you, life on the other side is really freaking awesome. It’s amazing how stable my emotions feel when I’m not dating someone who is constantly confusing and hurting me. Instead, I just feel content, wonderful and excited for what’s next…



All the break-up feelings.

21 Sep

By Cali

It’s likely that it will surprise very few of you to hear that the aforementioned gentleman and I have split ways. And if I am being honest, I can’t say I am all that surprised myself. Around July I realized that the guy I wanted him to be and the guy he actually was didn’t quite line up, and that his shortcomings weren’t just a result of “timing” as I had so wanted to believe. I very keenly remember the moment when I realized our relationship had an expiration date, and I also remember making the conscientious decision to continue with it, despite the obvious outcome. I knew it was foolish, but I was still having so much fun and I felt like I deserved to have some fun.

So yea, finding myself here, on September 21, 2014, sans Robbie in my life — definitely not a surprise. However, I can’t say I was prepared for how I got here. I mean, can you ever be prepared to have the guy you’ve been dating for 7+ months just abruptly stop talking to you, blowing off both your birthday and the wedding he had agreed to be your date for? I’m thinking no one is prepared for that.

While I always knew Robbie could be passive aggressive, had you asked me if I thought he’d ever do something like this to me, I would have told you there was no chance in hell. I would have told you that he is a 32 year old successful man, who claims to love me and see a future with me, and therefore could never be so childish as to just run with no explanation. And I would have been wrong.

It has now been two weeks since I’ve heard from him and I can tell you, those two weeks have been filled with a myriad of emotions. I keep waiting for one emotion to outweigh all the others, so that I can feel stable and feel like I’ve resolved the situation. However, I’ve determined I am a ways out from that place. And as I thought more about it, I decided that perhaps this is natural. Perhaps this is what a real break-up is like. And maybe there are others out there who can relate to this hourly zig zag of emotions. So I decided to write about it. You tell me if you’ve been here before…

I’m angry. I’m really fucking angry. And I don’t just mean about the break up. I am mad about all the shitty things he did along the way that I forgave because I was attempting to show grace and understanding. I’m angry for all the times I’ve cried over him (it’s an astonishing amount of times) and I’m annoyed that I can’t listen to John Legend’s, All of Me, without wanting to cry again. I’m angry that he lied to me, on more than one occasion. I’m angry that I had to listen to his constant stories about how his sad little ex was trying to get back with him, “and how it was never going to happen.” I’m mad that he tried to control what I shared on Facebook, when I tagged him, what caption I put, etc. And I hate that on the three occasions that I attempted to break up with him, he always managed to reel me back in. But mostly, I am so angry at myself. I’m furious with myself for allowing this guy to disrespect me, to control me, and to make me feel so small. I’m disappointed with myself for being reeled back in, and I’m angry that I wasn’t strong enough to say, yes the good times are the best times, but they come with this big-ass, pile of shit and I deserve better than that.

But I’m not just angry. I am also very sad. This is the first guy in my entire life that I could actually see a real future with. We’d talked about how we are such a power couple and how we fit so well together and I loved that vision of us growing old. I could picture our Upper West Side townhouse, and us walking the kids to school with our golden retriever. I could imagine us continuing our fabulous dates, even when we were old and married and I could equally picture us spending time together at home, making dinner, reading in bed and cleaning up after the gorgeous little blonde kiddos. And now, to know that none of that is going to happen makes me so insanely sad.

But it’s not just the future I miss. I miss him. I miss his big, strong arms around me, the way he’d pick me up, and how he’d hold my hand when we strolled around his neighborhood on one of our coffee walks. I miss the way he smiled at me, looking at me like I was just this funny, amazing little thing that he didn’t quite know what to do with. I miss his sarcasm, our witty text conversations and the ridiculously, amazing sex. But most of all, I miss the connection. I loved how close we became, how familiar he was to me and the feeling that he really, truly knew me — the real me. So yea, I’m fucking sad for the loss of all of it.

I’m also embarrassed. I’m embarrassed that he stood me up for this wedding and that I told ALL my friends how incredibly thrilled I was to be bringing him. When the bride texted me last week (having heard a rumor of our split) and asked if he was still coming, I wanted to throw up. How do I answer that? I assume he’s not coming since he isn’t talking to me, but he hasn’t really told me one way or the other… embarrassment doesn’t begin to explain that feeling.

I’m suspicious. Perhaps he never meant a word he said to me. Perhaps he’s been fucking other girls all along, and was just playing me for a damn fool. Or perhaps he’s now back together with the ex “who was never going to be the ONE…” and I was just a very long pause in their relationship. Sometimes I even think, perhaps he’s secretly gay…It’s New York, these things happen. I can’t help but wonder and question so much of the past 8 months given how it ended because, frankly, it just doesn’t add up.

I’m numb. Some hours I just feel nothing. It’s like this break-up happened to someone else and all I have is this foggy, empty feeling. The idea of loving someone else is unfathomable, but I can’t really remember loving him either. It’s like it was all a dream and now that I woke up, I just feel numb.

And of course, from time to time I find myself feeling vindictive. I won’t lie, I have thought of several elaborate revenge schemes, many of which involve calling his ex girlfriend. Part of me wants to show him he fucked with the wrong girl and that unlike all of his other ex-girlfriends, I am not going to sit around and mope, waiting for him to change his mind. You screw me, I’ll screw you right back, asshole. But ultimately, I fear I am just a bit too classy to act on any of these, which sucks because it would be really fun to make him feel 1/8th as shitty as I have been feeling.

But then, there are moments of zen where I just feel so grateful. I am grateful that I had my first “adult” relationship, even if it wasn’t always easy. I’m grateful that I fell in love and that he got me over D, who I haven’t seen in a year (despite the fact that he has rather consistently tried to get me to hang out with him every time I’ve been home). I’m grateful for the many, many elaborate, expensive and lovely dates we went on. IMG_20140921_180958_1No matter what, the day we spent yachting on the Hudson River will always be one of my favorite New York days, and I am grateful for that memory. I appreciate how much he taught me about what I want and what I don’t want, and how he forced me to grow. And honestly, I am somewhat grateful for the way he ended things with me. By being such an incredible douche he’s given me a reason to hate him, which will make moving on just a bit easier.

Last but not least, there is just this teeny, tiny portion of me that feels hopeful. I’m hopeful that getting myself out of this shitty situation will make room for something good. And I can’t help but think that if it can be that wonderful with a guy who isn’t the right guy for me, then imagine how amazing it will be when I am with someone who is.

So that’s where I’m at right now. Am I dealing with this break-up flawlessly? Definitely not. But I am handling it the best way I know how, and I think there’s some beauty in that. That being said, if you have any break-up pointers/tips and tricks, I am all ears. Feel free to leave me your pearls of wisdom in the comments.

The Most Important Dating Lesson

25 Jun

Post by Cali

Over the last 3 and a half years since starting Sex and the Twenties, I have learned countless dating lessons… Brads are bad, there is no such things as no strings attached, you can be friends with an ex, and of course, the very unfortunate one, throwback bangs are only good in theory. (Le sigh!)

And you know what, for the most part, all of this learning and reflecting has been an awesome thing. It has made me self-aware of patterns and reticent of repeating the same mistakes over and over.

However, I think all this learning comes with a price. Allow me to explain.

A little over 3 months ago, I shared a post with you all about the guy I was dating. To sum it up, I really liked him, but everything I had learned about dating in the past told me to run the other way. He wasn’t ready for a girlfriend, he was on the rebound, and he wasn’t too keen on discussing his feelings with me… clearly, if I were to make a decision based on past lessons, then this was an easy one. Walk away.

No surprise, you all agreed. The comments universally said I should let go of this, (actually every single one of them said run) and that I deserved better. And since it was the logical thing to do, I decided to do just that.

So, a few days after writing aforementioned blog post, I informed him we were no longer dating and that I’d like us to try being just friends. I figured, if I can be besties with Mr. Cute but Whiny now (true story), then there’s no reason he and I couldn’t maintain a friendship, amiright?

No, I was wrong. Our friendship lasted all of a week and a half, and was over the first time we hung out. To his credit, he went along with my friendship demands like a true gentleman, but I just couldn’t ignore my feelings for him. I was all over him in less than 2 hours. (I don’t know what to tell you, he’s really very attractive and I have no self control…)

After that night, I knew friendship was out the window, and despite all the signs to run and all the challenges, we’ve continued to date. It has now been a little over 5 months and while it hasn’t been seamless, it has been the best thing to have ever happened to me in my entire life. I am happy to report to you, anonymous friends on the internet, that I am very much in love and for the first time, dating a guy who it makes sense for me to be dating. We are so similar it’s scary (both in what makes us awesome and in our downfalls) and I love him for every aspect of him.

Now, while I’d love to pretend that you all are reading this just to hear the intimate details of my first real love, I’ll go ahead and cut to the chase. Here’s what I want you to consider… All of this happiness, a happiness I never had before and still sometimes don’t fully believe now, happened because I didn’t apply logic. I didn’t “learn” from my past mistakes and run away from something sticky. I waited, and put myself out there. And yes, I’ve been sad from time to time, (I’ve even cried….). BUT I can say without hesitation that it has been completely worth it.

Looking back at what I wrote in that last post only reinforces for me how much our relationship has changed (although I still can’t get him to officially use the world girlfriend…. blimey!). But he has continued to find time for me – canceling other plans in order to see me more than just once a week. He’s let me talk, incessantly, about my feelings and what I am expecting and where I want this to go etc. while being incredibly open and self-aware with me about his feelings. And best of all, his freaking ex moved out of my building and I was finally able to have him over for dinner.

Now are things absolutely perfect? Um no. I am not sure things are ever perfect for anyone. But this is by far the healthiest, most fun relationship I have ever been in. I am loving seeing what it’s like to let my guard down, to just be patient, and to have someone love you for yourself. I am (slowly) learning to be less dramatic about every little bump along the way and instead am working on just being secure in his feelings for me. And while I am excited for all the self growth this relationship has brought me, I am infinitely more excited by the fact that I just like this guy so damn much.

Which brings me to my original point. If there is only one lesson you take from reading my words for the past 3 and a half years, I hope it is this… sometimes you have to just throw out all the other lessons you have learned and just go with your gut. Dating isn’t scientific. It isn’t a guarantee that if you put the same variables into the same situation you’ll get the same outcome. Not to mention the fact that there is no such thing as the same variables. Every person is different, and just because dating one guy on the rebound blew up in my face, doesn’t mean I can’t be happy with another guy in a similar situation.

True, I can’t predict the future, but all I can say is that right now I am really really happy that I decided to ignore logic and go with my gut. Because maybe, just maybe, this “mistake” might end up being something real.

When Do You Walk Away

10 Mar

Post by Cali

I love Laney’s last post, I am Ted Mosby, because I have definitely felt that same way…. just so freaking tired of waiting for “the one” and critically aware of how desperate that statement makes me sound. I can all too well relate to the intense desire to fall in love; to just one time love someone who loves me back and have it all end happily ever after.

And yet, even though I so desire to get to that point with someone special, I am still unwilling to settle for just any relationship. This last weekend it became obvious to me that no matter how much potential there may be in a relationship, the relationship may not be able to survive if it isn’t something I can live with today.

As I’ve mentioned, I’ve been dating a lovely gentleman for the past two months and, suffice to say, I like him. We have great chemistry, I find him interesting and smart, we have a lot in common and I like the way he treats me – when we’re together. Part of me can’t help thinking, maybe just maybe, I have finally found that person.

However, there are also a whole heck of a lot of challenges that come with dating this guy, and it seems like all of these challenges are my problem. And after yet another weekend of feeling upset and let down, I’m just not sure I am up for continuing this with the hopes that things will get better. And more importantly, I don’t think I should be up for it… But I’d be curious to hear your perspective

So what are these “challenges” I am dealing with? Well, for starters, he’s pretty fresh out of a 2.5 year relationship. He broke up with this girl in November because (according to him) he just hadn’t been in love with her for awhile. And to be completely honest he seems very apathetic towards her, so that’s not the problem. But he’s also expressed a desire to be single for awhile and told me he doesn’t want to just jump into another relationship. He’s said that while he sees this going somewhere, he needs time to do his own thing for a bit.

Can I respect that in theory? Heck yea. But in reality, it’s hard being the one just waiting. The rules are all so unclear… Can I go on dates with other guys? Can I date the same “other” guy multiple times? Can I kiss other guys? Can I sleep with other guys? What if I develop feelings for another guy, then what?

And while two months in I am not at my breaking point with all this grey area, I’m not really getting any signs that we are progressing in any sort of timely fashion. Somehow, I think 6 months in I will be having a lot more trouble being zen with all the waiting.

There’s also the fact that he is exceptionally busy. Yes, this is New York City, and yea, most men are pretty damn busy; but this gentleman is maybe one of the busiest. He works in an industry that constantly requires client dinners, drinks and travel on most weekends — leaving very little time for a budding romance. And while he’s made an effort to share the time he does have with me, I’m not sure I am into this whole,  “I see you once a week, on your time-frame” thing. I also have a social life, and having to arrange it around his schedule is frustrating. But more importantly, I feel like expressing said frustration is off the table. Apparently he felt like he always had to justify work obligations in his last relationship, so I get the impression that I am just supposed to shut up and deal with it. But can I? Not sure.

Another fun little piece of baggage weighing down this romance is his ex. First off, she doesn’t seem to be over him, even if he’s over her. She’s texting, emailing, showing up at his place drunk….eeesh. And while he says he didn’t let her in, and isn’t encouraging the behavior, it’s very reminiscent of  what happened with Mr. Cute but Whiny. I don’t like it.

Furthermore her presence isn’t just limited to his phone, email and doorstep…. oh no, this lovely young lady just so happens to live in my building. Fact. Of all the buildings in New York City, I happen to live 6 floors below this gentleman’s ex-girlfriend. And despite it being a big building, I’ve run into her 3 times in the past month alone – awkward. But awkwardness aside, because she lives here the gentleman will never come to my house. He says (and I do actually agree) that it would just be too disrespectful to her to show up in her apartment building, with another girl after he dumped her. Ok fair, but always going to his house means I am always the one traveling. I am the one paying for the 30 dollar cabs or taking the 40 minute subway and it is just one of many ways that I feel like I am putting in far more effort into this thing than he is.

But the biggest challenge of all is  this: because it’s obvious that he is SO not ready to be in a relationship, I constantly find myself walking on egg shells. When I’ve tried to talk to him about getting together, if he sees a future for us, or anything even remotely related to my feelings — it’s like talking to a wall. He just shuts down,  gets defensive and blows me off for a few days. And while I know that’s just yet another symptom of him needing time, I can’t pretend like its not hurtful. It’s hard to be the one dropping everything to see a guy, doing everything on his schedule, catering to his needs and yet being afraid to ask for anything in return. And I’m not someone who wants to talk about my feelings all day every day but freaking throw me a bone every now and then!

So at this point, I feel pretty clear on what I need to do. Do I want to throw away something good too soon because of a few issues? No. But I think there is a difference between a few issues and timing that is just plain off. And even if he was ready for a relationship, would I be cool with just seeing a guy I was dating once a week? Would I be cool with constantly rearranging my schedule to fit his? I just don’t know.

And then there’s one other question I keep asking myself – what else am I missing out on while I am sitting around waiting for this guy? Yes, I like him a lot….but what if there is a guy out there who I could like even more and who would be more willing to include me in his life. What if there was a relationship out there where it just wouldn’t have to be this hard and where it might be a bit more two-sided?

So what do you all think? Would you let it play out if you thought that despite how shitty it is right now, it had potential for the future? Or would you kindly let him know that, for now, you are only interested in friendship until he feels a bit more ready to be an active participant in the relationship? If you all could kindly let me know, I would be ever so grateful.

Many thanks. CB

For the Guys: 16 little ways to stand out from the boys.

17 Feb


By Cali

I’ve recently started dating a guy who I am beginning to really like. He’s smart, successful and handsome and I have fun with him whether we’re watching TV, out at dinner and drinks, playing board games with his friends, or just making out in the snow. But what’s been really cool about dating him is that I realized this may be the first time ever that I’ve not only liked the guy I was dating, but also liked the way he treats me. Maybe it’s because he’s older, maybe it’s because he’s used to having a girlfriend, or maybe he is just a good guy… but whatever it is, I end up feeling pretty special when I am with him. So, my lovely gentleman friends, should you be interested, here are a few little things you can do that will make you stand out as a keeper.

16 little ways to show a girl you are a gentleman

  • Help a lady into her jacket
  • Hail her a cab
  • Offer your hand to help her out of her chair/booth
  • Offer her your arm/hand when walking in the slippery snow (this one I am extra grateful for)
  • Wait for her outside if she is coming over
  • Offer her a drink/wine and then make it for her
  • Introduce her when you run into people
  • Open doors (a classic, but worth mentioning)
  • Give her a little kiss hello and goodbye
  • Sit by her when you are in a group
  • Hold her hand under the table
  • Walk her to the subway
  • Pick up the tab (yea yea, I know some of you object to this one, but it’s part of the list. Because it makes me feel special as hell)
  • Tell her when she looks or smells nice
  • Call her, like on the phone
  • Send her pictures when you are away. We know you’re busy, and you don’t have to send “I love you” snapchats, but it’s great to hear from you and to know that, at least for a second, you were thinking of me.
So there you have it… These are the 16 things I have noticed in my past month with this gentleman that I have really, really liked. I can’t say I am certain as to what the future will hold for us, but so far I am optimistic that this could potentially be something great. And I have not only noticed his efforts to make me feel special, but I have attempted to reciprocate. I have put myself quite a ways out of my comfort zone to make sure he knows I like him and that I want to see where this goes. So fellas, even if your motives aren’t entirely altruistic, perhaps incorporating some of the above may help you get what you want. ;)

It Is All Facebook’s Fault…

28 Jan

By Cali

Tonight I’ve had an epiphany (albeit fueled by multiple dirty martinis but none the less, an astute observation). You guys, the root of all our dating anxiety, all of our problems, is one sole, festering problem – Facebook. You know I’m right, right?

Ok fine. I can’t attribute all of the many diverse dating problems I’ve had to Facebook- SOME have been related to green cards – but for the purposes of this post, Facebook is getting my wrath because at this exact moment it is evil and I hate it.

So what’s my latest beef with Facebook? Well there are many. Allow me to take a moment to share them with you.

The 7 reasons why Facebook is ruining my (dating) life.

1. The “seen by” notification on your messages. What the hell?? Does anything hurt worse than a message that has the little words “seen December 6th at 9 PM” and no accompanying response??? I’m going with no. When a friend blows you off it is irksome enough. But when your message offering to give your airline miles to a certain British gentleman is ignored — that’s a whole new level of harsh. Ok sir, noted. Me and my miles will go elsewhere. But really, F you Facebook. If you didn’t have the stupid “seen by” notification I could have told myself, poor darling is too busy with school and work and I would have put my pride aside to try and reach out again. But no… I cannot. Because those damn words haunt me on my final message to him, reminding me that he DID indeed read that message and chose not to respond. And now I’ve had to cross that unrealistic romance off the list, a fact that I am exceptionally bitter about because you know what, it was fun to think about.

2. The new girlfriend. Yep we all break up, and then move on. It’s life. But having to see pictures of the girl he is moving on with in your news feed is effing torturous. Especially when you aren’t friends with him OR her and yet her rotund face still manages to make an appearance.

And ya know what?  Seeing her play “happy girlfriend” might not be so irksome if her boyfriend hadn’t sent you texts 7 whole days ago saying how much he loves you and wants to visit you. I’ll have you all know it is taking all (and I do mean ALL ) of my willpower not to screenshot that shit and leave it as a comment. Get out of my feed beeze. Next time I may not be so rationale. 

3. The stalking opportunities. So you move to New York and meet a really great guy, yaay! And let’s say you purposely don’t friend him on Facebook, because as mentioned above, you feel like Facebook may just be the root of all evil in relationships. Butttt then all his best friends “friend request” you… Are you going to say no? Um no, that would be rude!

And let’s be real, once you accept it’s not like you aren’t going to look through a few pictures to see your handsome new leading man… oh… and his ex girlfriend.

Fast forward to an hour later and you find yourself on the ex’s profile, lamenting the gorgeous flowers he gave her and telling yourself he’s never going to love you as much as he CLEARLY once loved her. Perfect and totally healthy!

4. The Ex’s engagement. Does it matter that Mr. Not  Quite Right looks old and sort of horrible (is he balding??)? Nope. Because there is his little baby girlfriend, looking smug and finally rocking a diamond on her left ring finger. I always knew this day would come, and intellectually, I was prepared for it. There is ZERO percent of me that wishes I was living in San Marcos and marrying his boring ass. BUT, I hate seeing all the congratulations, and the ring, and the smiles. And worst of all, I can’t help but wonder what he thinks of me. He’s probably like, “Oh that Crazy Cali. It’s so sad really….. she moved to New York and just goes to parties and dates and travels all the time. How sad her life must be!” And even though I don’t feel that way about my life, the idea that he might bugs the shit about me. Irrational, I know, but true. (And if you can’t be irrational and truthful on your own anonymous blog, where can you be?)

5. Bitches on Facebook be crazy. Last month I learned that my best guy friend in SD and his girlfriend got in a massive fight over my Facebook activity. Why you ask? Well apparently, being the brilliant genius that she is, she had deduced that I was in love with said guy friend because I only “like photos she isn’t in.” No really, I can’t make this shit up.

And even though everyone told her she was absolutely wrong and that she was reading WAY too much into likes, she disbelieved them  so much that she actually went into his messages to check what we talked about. #Crazy. So not only is Facebook ruining my dating life, it’s ruining my guy friend life… Freaking fabulous. 

6. You can see me, but I can’t see you. So I have the majority of my posts marked as public… Why? because I am an open book and I am not ashamed to the things I do or the places I go. OR because I hope that every asshole I have ever dated and subsequently un-friended occasionally checks up on me and thinks, damn her life is fucking fabulous… It’s definitely one of those reasons.

Regardless, the fact that I am somewhat “on display” is a Facebook reality I have come to accept… that is until I start dating someone and they inform me that they have creeped on me on Facebook. Now, I wouldn’t care if said fellow then “friended” me, or had ANY aspect of his profile public. But he has not and does not, and hence I am left feeling like I am getting the short end of the stick. Soooo you get to see everything about my past and I get a picture of your golden retriever?? Boo.

7. The oh so in love cheater.  Go ahead, sir… Put up as many photos as you’d like of you and your girlfriend on vacation or kissing in front of the tree… it doesn’t change the fact that a month ago you were making out with me and begging me to get a hotel room with you. You and Facebook are both liars and I, for one, have no interest in participating in said duplicity any longer.

And you know what, I am sure this is JUST the tip of the iceberg…. I bet if you asked 100 people, “What’s pissing you off about Facebook right now?” they could rattle off a list of at least 3 things each. Let’s be real, probably more.

Now, I know the mature and responsible thing would be to not blame a social media platform for my current dating angst, however, I am not in a mature and responsible mood at the moment. So instead, just for tonight, let’s put all the blame for our dating troubles on The FB, because even if it isn’t the root of all dating issues, it sure does add fuel to the fire and thus warrants at least an evening of our wrath. Feel free to join in with your own ire in the comments…

How to be Single at Your 10 Year Reunion

2 Dec

By Cali

This weekend was my 10 year high school reunion… and gasp… I was single. I won’t lie, I was having some pretty conflicted feelings leading up to this event. On one hand, I am truly loving being single right now. I feel like I have finally figured out how to do single “right” and I am having way more fun than is probably responsible.

On the other hand, how could I not feel awkward that a 10 whole years had passed and here I am, STILL single… I was dreading being the cliché — the girl with the amazing job and life who everyone trades small, pity smiles about because she just can’t seem to meet the right guy. And heavens knows I couldn’t very well tell everyone, “Hey, ya’ll don’t feel bad for me… I’m making out with people left and right – I’m doing just fine.” Somehow, I didn’t think my classmates with their 3 kids and mortgages would be able to appreciate my current lifestyle…

But even after weeks of vacillating feelings, the idea of not attending never even crossed my mind. I loved high school and I was excited about the idea of spending a night with my fellow cheerleaders and my favorite football guys. And besides, boyfriend aside, my life is going freaking fantastically. While I may not have pumped out a little baby or three just yet, I certainly have plenty of things to be proud of!

So I decided I would just embrace my singleness and go. And you know what? I had a freaking blast. As it turns out, being single at your high school reunion can actually be amazing if you do it right! And since it went so swimmingly for me, I thought I’d pass along what I learned.

Here’s how to be single and awesome at your 10 year reunion.

  • Remember you aren’t alone. Prior to the event, I had a couple of fun Facebook updates about being single at my reunion, each of which got a whole lotta love. As I read through everyone’s comments I was quickly reminded that I would absolutely not be the only one in this boat. Of course no one plans to be single at their reunion, but it happens — to even the most awesome of us.
  • Set the stage. These aforementioned Facebook updates also served another (unintentional) purpose – they gave my fellow attendees a heads up on my relationship status. No need to ask me if I am “seeing anyone special” – I’m not. And not only did this help me avoid being asked that annoying question, it lead to a whole bunch of people telling me they loved my Facebook status and that I am hilarious. Soooo I’m single but funny… I’ll take it.
  • Go with a group of friends (and at least one other single, preferably). We had a lovely little pre-game at the bar across the street so that we could roll up as a group. No one likes the feeling of walking in alone so don’t do that to yourself.
  • Keep in mind that even the happily married and coupled may not have their significant others with them. In fact, I was a little shocked at how few people actually brought dates. I would say that maybe 40 percent of the people there had dates and the vast majority of these people had married or were dating someone from our high school.
  • Wear something fabulous. This is really just my rule for life but realistically, you probably look a lot better than those ladies who started pumping out kids at 22 and you should flaunt it. I’m never a fan of trying too hard, but I may have gotten a a tiny bit of satisfaction knowing that my leather jacket cost more than those moms and dads will likely spend on their wardrobe all year. Perks of limited responsibility!
  • Talk to the marrieds. No really. It’s hilarious. I can’t tell you how many of them told me they were living vicariously through me.. It’s truly such a good reminder that the grass is always greener on the other side. There was one particular conversation that I’ve had a hard time shaking. One of my favorite guys of all time was telling me about how the summer we all hung out (back in 2006) was one of the best of his life and how everything changed for him after that (he now has 2 kids and a wife preggers wit a 3rd). The idea that THAT summer where we all just got drunk and ran around Encinitas was one of the best of his life made me so, so sad. I’ve had a million and two other experiences that have topped that and I plan to have many more! I am positive married life is lovely, but there is no doubt that many of my more settled classmates expressed at least a smidge of jealousy for my lifestyle, and that didn’t feel bad.
  • Feel grateful that you don’t have to worry if you significant other is having fun or what others think of him/her. One thing I underestimated was how many people there I actually wanted to talk to. I was literally running around trying to talk to every single person and having entirely too much fun reminiscing and catching up. I can’t imagine any second of that would have been fun for someone who hadn’t gone to high school with us.
  • Flirt a little. Sure, I never really thought anyone in our grade was particularly good looking or interesting (and that certainly hasn’t changed) but it’s definitely entertaining to flirt with people you’ve known for forever. Also entertaining to see which guys whose girlfriends didn’t make it had NO problem being inappropriate. So much for being grown ups.
  • Take in the compliments.If you are one of the “few” singles at the event you are likely going to get a lot of attention … so yaay, you get to soak it all up. I loved the guys who were like, “I just don’t understand how a girl like you is single?? How does that happen?? Ohh stop sir… ok ok go on.
  • Have somewhere to go after. After you’ve enjoyed the awesomeness of connecting with old friends, what could be better than getting to go and have some great (albeit likely irresponsible) sex. You survived being single at your reunion. You earned it.

So there you have it. That’s how I not only made it through, but enjoyed, being single at my 10 year reunion. I think it comes down to this – I am truly (for the first time in my life!) so happy being single right now, and I am not going to let little things like 10 year reunions or Mr. Not Quite Right’s recent engagement, deter me from said happiness. I could have let these things bring me down, and I could have got caught up on what I thought people might think or how I “should” feel, but I was able to catch myself and just have fun.

All in all, my reunion was a great night that reminded me how much I loved high school and how lucky I am to be where I am now. So should you find yourself in a similar place (single and debating on whether to attend) you can rest assure that I recommend you go. If you opt to skip it rather than deal with the stigma of being single, you’ll be depriving yourself of a quality night and likely an ego boost :)

Are One Night Stands Bad?

27 Oct

By Cali

Four months ago, I found myself at a bar in Chicago when an amazing Englishman walked up to me. Fresh off my “break-up” with the first guy I dated in NY (Brit 1.0), I was in a bit of a dating funk. I had spent much of the previous two weeks licking my wounds from the 1.0 crash and burn, and trying to figure out what my next move in the guy department would be. Should I jump back into NY dating scene and risk letting yet another guy crush me? Ouch, wasn’t sure I was ready for that… Perhaps I should run back to D on my next trip home to lessen the sharp pain of rejection? No, that didn’t sound right either. There had to be another choice, right?

Well, what I didn’t know yet,  was that this gentleman in the Chicago bar (we’ll call him 2.0) was, indeed, offering me a 3rd option — one that I think actually saved my dating sanity at the time. And one, that you may even say, changed my life.

Allow me to explain.

When 2.0 sat down I liked him immediately. Sure, I undeniably have  a thing for the English accent and the proper use of grammar (how could you not…) however, it was his mix of sarcasm, politeness and charm that made me laugh and smile for the entire 2+ hours I talked to him. I don’t remember much of what was said, I just remember thinking, why the hell are guys like this so rare??

After we talked for a few hours, 2.0 said he should probably get back to his friends (who he was in Chicago visiting). He told me it was  too bad that we lived countries apart, because if circumstances were different he would definitely be getting my number, and then off he went, leaving me sitting there all sad and forlorn.

As a few more minutes went by I realized, this guy was a genius. I hadn’t been this interested in making out with a guy in a very long time. If this was game – it worked. Well played, sir.

Fortunately, I didn’t have to wait long until he was back and after more chatting, we were off to find another bar – just the 2 of us. Or at least that was the plan until we realized it was 2 AM and not actually that easy to find an open bar. So, instead, we opted to head back to my hotel room. Now, I’d love to claim that I am a stranger to taking men back to my hotel rooms, but that would be a lie. I’ve done it on at least a few occasions. That being said, I never sleep with them and in most cases it has been an ex, or a friend, or something of that nature rather than just some random. But I figured, what the hell — we’ll go back, we’ll make out, we’ll cuddle – it will be swell. And honestly, it never even crossed my mind that I would sleep with him. I had never, ever, slept with a random in my life (not for lack of opportunities) and besides, I had spent ALL day eating crap — I looked like hell. There was no way I was getting naked in front of anyone. Or so I thought…

So, back to my hotel room we went, and when we started making out, something just came over me! I was thoroughly enjoying kissing this guy and found myself really, really wanting to have sex. As I kept trying to think of a reason not to, I realized I couldn’t come up with one. It’s not like sex would nullify a chance of a relationship… This dude lives in another country — I was clearly never seeing him again. And it’s not like all the times I had forgone sex had worked out so swimmingly for me. Perhaps I needed a new strategy. Besides, I told myself, I really needed some sex in my life. A large part of the reason I was even considering calling D when I returned home was that I was pretty much dying to have sex. So I figured, if I had sex with this random instead, I would no longer “need” to see D.

But the real truth was, I just liked him and I wanted to sleep with him. And so, right then and there, I just forgot about my insecurities/rules and went for it. And holy hell — best sex ever. Seriously. We had sex once that night, then cuddled all night and had sex twice in the morning… All of which I found very enjoyable. The intriguing thing was, in between all the sex we were talking and what not, and even in the harsh daylight and sobriety, I was still really liking this guy. Perhaps it was because I knew I’d never see him again, but I wasn’t worried about what I was saying, or what he was thinking, and I was just being me.

When he finally had to go, he kissed me goodbye and said, “Well I guess I am just going to walk out of your life now.” I very vividly remember this exact phrasing because when he said it I got a really overwhelming feeling of ick… But what could I do? We live in different worlds and we had said this would just be a fun one night thing. So, I just kissed him goodbye, wished him well on his way and began packing.

However, it didn’t take me long to decide to try and find him on Facebook, and after an hour or so of my best stalking, I successfully located his profile. Trying to appear cool, I sat on it for a few days, and then sent him a friend request with a note that said, “Just in case you ever make it to NY ;).”

In all honesty, I was totally prepared for him to ignore my friend request. It was a little stalker-esque to find him on FB. Furthermore, if Brit 1.0, who I dated for an entire month has ignored my friend request, I couldn’t really expect this guy to feel he owed it to me to stay connected after just a few hours. But I figured, on the offset chance that perhaps he had felt a little sad walking out that door too, I’d give him this opportunity. And if he didn’t accept, oh well. It was still awesome sex.

Well fortunately for me, 2.0 did accept my friendship and sent me a message saying that he would absolutely let me know if he was ever in NY. And at the time, I thought, great, my work here is done.

As it turns out, that was just the start. We began talking online, mostly just flirty, little short convos here and there. Then, when I got offered a speaking gig in London (a few hours from where he lives) we began planning a little rendezvous while I was in the country. We even had a Skype date once, and slowly but surely, I was starting to realize I had a legitimate crush on this guy. He’s exceptionally witty, cleverly complimentary and clearly quite smart and motivated. And the more I talked to him, the more I was looking forward to seeing him again.

But even as we began to plan out the specifics of our night together in London, I was still expecting him to bail out at the last minute. I kept telling myself, this guy barely knows you, you had a one night stand in Chicago and he is going to find plenty of reasons to not spend 6 hours commuting just to see you… D knew you for 10 years and the farthest he ever drove to see you was 30 minutes. Once. In 10 years.

However, I was wrong. Last night I opened up my door to see 2.0, at my doorstep, right when he said he would be. And without boring you with the lovey-dovey details, I had the nicest 24 hours with that man. It was amazing because on one hand it felt very much like a first date, as we still have so much to learn about one another. But in a lot of ways we were just so comfortable and natural together that it felt like we’ve been dating for years. Who knows where this will lead (if anywhere) but the future is irrelevant. Right now, this one night stand has provided me with a whole lot of awesomeness.

Specifically one night stand made me believe that not all guys are assholes. It made me remember that I AM capable of liking a guy. It taught me that guys do show up for you, and that some guys want to do more than just have sex with you. It showed me that I can have really incredible sex with people other than D. And for that matter, it put the nail in D’s coffin. But most importantly, this one night stand got me to accept a speaking gig in London, something I may not have done otherwise as I’ve never traveled on my own before. This trip was transformative for me outside of my time with 2.0 and I’ll go home tomorrow just a slightly different person.

So, had you asked me to answer the question I posed in the title of this post 6 months ago, I would have told you that while I don’t think one night stands are bad, I know they are something I would never do. Had you asked my advice, I would have told you there’s no way anything good can come out of sleeping with someone you don’t know, the first night you meet them and that it would be best to avoid doing so. And I would have been dead wrong.

Now, are all one night stands going to go this way? Not likely. But I am so glad I went with my gut that night and that 2.0 is now a part of my life. And I encourage you, should you ever be in a situation where your gut is telling you to go for it, to consider doing the same. You never know where it might lead…


How to Answer OkCupid Questions

25 Sep

By Cali 

I was recently on an OKCupid date with a charmingly nerdy lawyer when the topic of OKC questions came up. For those who haven’t used OKCupid just yet, allow me to catch you up…

OKCupid has this section where they ask you hundreds and hundreds of multiple choice questions on everything from mathematical riddles to your sexual preferences and your politics. They then take your answers and use them to give you a percentage match rating between you and potential dates. Seems pretty straight-forward, right?

Well, it would be except that these questions go FAR beyond what you would expect them to ask. The OKCupid questions can be downright ridiculous, thought-provoking at times, occasionally offensive but always addicting. Don’t believe me? A few of my personal favorites include:

1. Would you consider performing anilingus on a partner who asked you to? Yes or No

2. Which pubic hair style do you prefer on your partner? Nature, neatly trimmed, completely shaven or it doesn’t matter

3. Are you more horny or lonely?

4. Which would do more to improve the world? Fewer stupid people, fewer ugly people or this question upsets me

5. Imagine you have an identical twin. You’ve had many sexual experiences, but they remain a lonely and frustrated virgin. Would you secretly swap places to give them ‘a piece of the action’? Yes or no

6. When you hear the name Dylan what is the first to come to mind? Bob Dylan, Dylan Thomas, 90210, something or someone else / Nothing

7. Which most closely describes how you organize your sock drawer? I pair them before I put them away, I pair them when I get dressed, I have them paired and organized by color, I take them out of the laundry when I dress

8.You have a one-time opportunity to use a machine with a numbered dial, which, when turned, adds that number to both your IQ and your weight. What do you do? Turn it up — I’d love the extra smarts, turn it down — I’m smart ‘n’ chunky, don’t touch that dial — I like myself as is.

You can see how answering these could get entertaining, right??

But I digress… Back to the date. approximately 3 vodka sodas into our evening, the lawyer asks me if I read through his questions prior to meeting him. The true answer? Yes, of course I read every single one of the 400 something questions he answered (see above, regarding addicting…). However my response was something along the lines of,  “Oh maybe I might have seen a couple…”

And then he asks me if  I remember any of his answers – a question which definitely made me cringe. Remember them? Um yes, there were quite a few gems in there that I was wishing I had never read and had been thinking a lot about ever since going through them. In fact, after reading through his questions I had strongly considered not meeting him at all because I feared he might be a bit of a douche. However, instead of explaining all of that, I just blurted out, “I remember you’ve had a threesome!”

He understandably fumbled a bit with responding to that and looked pretty darn embarrassed… clearly someone hadn’t really thought through his audience while answering  all those OkCupid questions. And you know what — I really can’t blame him. It’s something about how they ask them, it sorta feels like a Cosmo quiz and you forget that the answers are public for potential suitors to see. It’s so easy to get caught up in the fun of answering, that you forget that there are, gasp, SOME things that your date doesn’t need to know before they ever meet you.

So in order to help us all keep it straight, here is my best guide on how to answer OKCupid questions:

Avoid the sex questions – I know, I am no fun, but seriously, no one needs to know this much about your sexual preferences prior to ever shaking your hand. There is a time and place for sharing your love of S&M, group sex, hickeys, up the butt, video-taping and more and it is not before the first date. Here’s the thing, even if I think video-taping a sexcapade might be sexy, I am still going to get a little skeeved out if you mark, “yes I’ve done it and loved it.” Why do I need to know what you and some ex-girlfriend did in the bedroom? I don’t. And I can only imagine that if I were to ever sleep with one of these guys who answered yes to threesomes, videotaping and S &M, I’d feel incredibly stressed out that he wasn’t enjoying our regular old vanilla sex.

Add Context – It’s no surprise that sometimes you need more than a few multiple choice options to explain your feelings on relationships, love, life etc…

However, so FEW people add context to their OKCupid answers and I think this is a big miss. Take my friend the lawyer…. on multiple occasions he indicated he couldn’t date a girl who was even slightly overweight; answers which left me thinking 2 things: 1. Wow this dude must be pretty darn pleased with his own body and 2. What does he consider overweight? I won’t lie to you, my life in NY has involved a ton of amazing parties, dinners, dates and fun – leaving my waist line with a few extra pounds. Do I think I am fat? No.  However I definitely found myself wondering if I should even waste my time. Maybe this guy was only into rail thin model types and that’s not me.

As it turns out, he seemed to find me attractive (or at least his kiss said he did) and I got the impression that his “skinny” answers had to do more with his past experiences on OKC than his actual life preferences. According to him, he had met quite a few “stealth fatties” on the site in the past and was hoping to avoid being duped again. Had he (delicately) explained that when answering his questions, I might have met up with him much sooner.

Side bar, I really enjoy the term stealth fatties. It’s mean, but also pretty darn funny.

Don’t answer questions that make you look bad – This really shouldn’t have to be included, however, it seems people approach these questions like they are  a required test of some sort. They aren’t! Don’t be shy to skip questions. There are some topics that can ‘t be tackled in a multiple choice question no matter how much context you add. For example, I always skip the “How long do your relationships usually last?” question. Hmmm let’s see, D and I were on and off for 10 years…. and if that doesn’t scare someone off, than the fact that all the rest of my relationships ended after 2 months definitely will.

The reality is, you could have 500 awesome answers and still 1 scary answer could send a guy/girl running. I mean hey, they’ve never met you, they don’t know how amazing you are in real life, or why that scary answer should be overlooked. So it’s no surprise that they might just bail.

Time your answers strategically – Every time you answer a question your adorable little picture gets served onto the OkCupid news feed, displaying you to a whole new set of potential suitors. So choose a smart time to answer these questions (eg around 8-9 PM) when everyone is just chilling on OKC, wishing they could find their future significant other. You’ll be stoked at how many messages you get without even having to browse matches.

Go back and edit – As aforementioned, answering these questions can be super addicting and sometimes you find yourself, an hour later and a hundred questions deep, without even realizing it. So take a little time, go back, and read the answers as if you were a member of the opposite sex. Are your answers helping your case or hurting it? If it’s the latter, either add context, or make the question private.

I’ve also noticed that sometimes, I pick a certain multiple choice answer because of a particular mood I am in (eg  “No I do NOT believe in true love” after a particularly bad date). During those times I feel it’s best to go back and respond more accurately.

So there you have it, my top 5 tips for answering OKCupid questions. Hopefully this helps you avoid scaring off someone before they can meet you, fall in love, and decide to not care about all those “scary” truths we all have. Or at the very least, hopefully this helps you get more dates.