I’m My Own Worst Enemy When It Comes to Dating

Bridesmaid he was cute so I ran away

I wish I could say that this post comes with some sort of advice or lesson learned. It doesn’t. This is a way for me to try to work out a problem I’ve always had. A problem that I cannot even begin to explain. Maybe some of you lovely readers will have some answers. If nothing else, maybe I’ll be able to find some fellow weirdos who can relate.

It all started at a very young age. Probably in the third grade with the first boy who had a crush on me. He was so sweet. When I was out sick for a week right before the holidays and my dad came to school to pick up my homework, this boy gave him a present for me. It was a stuffed animal with a note hoping that I’ll feel better soon. That was incredibly sweet and showed bravery. An 8-year-old went up to my father to give him a present for the daughter that he has a crush on. This crush went nowhere. I didn’t even hold his hand (the equivalent of getting to third base when you’re eight). I immediately friend-zoned this poor guy.

Maybe I just didn’t like this little Romeo. I’ve already went over how just being “the nice guy” isn’t enough. But I have a history of turning away the boys I’ve liked as well. My first date was in the fifth grade to see Liar, Liar with a boy I really liked. Halfway through the movie, with my date constantly trying to put his arm around me, I came to the realization that maybe I don’t like this guy after all. Needless to say, this was our first and last date. Then for my sixth grade prom, the boy I had the biggest crush on actually asked me to be his prom date! I was ecstatic for a day before I started to question whether I actually really did like him. Turns out I didn’t so I had a friend tell him that I couldn’t go to the prom with him. (I am fully aware that I am coming off as Regina George-levels of mean and maybe I was when it came to these poor boys. But I really didn’t do it intentionally.)

This cycle of being a weirdo followed me into high school. I was a loser in high school. Braces, glasses, and a back brace will do that. I didn’t stand a chance. But there were a few boys who actually showed me attention. What did I do? I bet you’ll never guess. I ran away! One boy, who was tall, cute, and played football, inexplicably showed interest in me when I was a freshman in high school. I immediately closed up whenever I saw him and would go out of my way to avoid talking to him on the bus or in the hallway. A big part of this could be attributed to confusion. I just went over what I was packing in high school. I thought that this dude was playing some kind of cruel trick by being nice to me.

I wish I could say that after I left my teenage years, things got better. They haven’t. In fact, they have just gotten worse. There have been boys that I have genuinely liked. Truly cared about. But it’s always been at a distance. I never truly let them in. The second I feel as though things may be starting to get serious, I find some excuse to bail. No person in this world is perfect so if you try hard enough you’ll always be able to come up with an excuse to leave them. There’s always something that you’re not going to like. When I find that something, I convince myself that it’s a deal breaker.

There was one boy in my life that I let get to me. One boy that I actually cried over. It was a boy I met in college. He was really into me and always tried hanging out with me but surprise, surprise I kept putting it off. This happened for two semesters. Then finally he reveals to me that he got a GF so we stopped talking. Fast forward a little over three years and he calls me out of the blue. We start dating even though he was only 3-months out of a long-term relationship with the very girl that caused us to stop talking so many years ago. This guy was a walking red flag but I didn’t care. I went along with it anyway cause I actually liked him. A boy I actually liked and wanted to spend time with! I couldn’t pass it up.

Naturally things started to go south rather quickly. The texts got less frequent, something always came up when we were supposed to hang out. Eventually things ended cause he was still hung up on his GF (they even went to dinner one night while me and him were supposedly dating). I knew he was hung up on his GF, I knew he was emotionally unavailable, but I went along with it anyway. Nonsense with this boy went on and off for a little over a year before it ended for good. I know you guys are shaking your end at me for thinking getting into a relationship with a guy right out a long-term relationship was a good idea. Trust me, I’m shaking my head at myself. Maybe the allure of him being emotionally unavailable is what pulled me in.

Things still haven’t gotten better. This February, I met a boy. A tall boy with GREAT hair, who had his own place and made me laugh. He made an effort to take me out on real, proper dates. He cooked me dinner. The first time he did, I went to his place and the table was all set and everything. He also made me feel really pretty. He was incredibly complimentary, and not in an annoying, “just saying you look nice cause I should” way. He was so genuine in his compliments. Any normal girl, after coming across a guy like this would be elated. Unfortunately, we’ve already established that I’m not a normal girl. I literally found everything to discredit this guy. “He’s really clingy.” “He texts a lot.” “He wants to hang out all the time.”

(You are completely justified in judging me while reading this and please feel free to be mean to me in the comments section. I need it.)

Fast forward a few months later, I’ve found a way to sabotage things with the boy from February and I’m getting ready to be set up with my brother-in-law’s friend. Things are good for about a week before they start to go south. Regular readers will be familiar with this one. He’s the infamous almost relationship boy. This boy has been trouble since day one yet I keep coming back. (Yep, he is still in the picture.) It’s as though him being emotionally unavailable and a dick to me, is the way to my heart.

I’ve expressed my concerns about my dating habits to the people closest to me. I fear that I’m not actually capable of falling in love. There has to be something wrong with me that I can’t find anyone I truly like. I fear that I may have met the one for me but in my own stupidity I let him get away. (I still think about the boy from February a lot and genuinely miss him.)

They all tell me the things you’re supposed to say to someone when they are single and complaining: “You just haven’t met that special someone yet. He’s out there.” I get the sentiment and it’s the right thing to say, but it’s not always true. Not everyone finds their special someone. We all know at least a few people in their forties who never settled down. And if I’m being completely honest with myself and letting my guard down, that’s one of my biggest fears. I like being single. However, I don’t want to be alone forever. It’d be nice to find that person I could share life’s ups and downs with. But sometimes I feel as though I’m not capable of it.

I am not big on New Year’s resolutions. They are stupid and usually never actually work out. But if I had to commit to one thing in the upcoming year, I’d like to be less of an idiot when it comes to dating. I’m FAR from perfect and I need to remember that so is the person I’m dating. If they treat me right and make me laugh, then I shouldn’t be going out of my way to find things to dislike about them.



  1. I’d actually say that you’re behavior is fairly normal, you’re just on a different level than others. Basically, you want what you can’t have. Once again, normal. It doesn’t mean its easy, but with all of the movies of grand gestures and undying love, we have to remember that those things are not necessarily real. I’ve received a couple of grand gestures but in real life, it’s incredibly awkward and weird because you don’t have some sappy love song playing in the back or a crowd to cheer you on when you kiss. I’ve done many of the things you have where the guy really really liked me and was incredibly nice and it just freaked me out. Here’s to hoping you find that best friend whom you can call “lovah” soon.

  2. I love your honesty in this. Dating is so frustrating. I was single for three and a half years where I would go on COUNTLESS dates and they were always first dates, never second dates. After awhile you become numb and forget why you’re even trying so hard in the first place. Even with my current boyfriend I got scared and almost ran away because I was scared that it was too good to be true. Because love is fricken scary. Realizing you’re scared and accepting this is a huge step.

    This is WAY easier said then done but ditch brother in law guy, he’s not who you want. Call up February guy, say hey-I suck at this dating thing let me buy you coffee. Reaching out to say you messed up (I think you’re saying you did, my apologies if I’m wrong) to him is the equivalent to a romantic gesture now a days. And if he’s as great as he seems then I bet he’ll take you up on the offer. Of course, you don’t have to listen to me but you seem like a confident woman, I think you’re just scared and there’s honestly nothing wrong with being scared to fall in love.

    P.S. If he has great hair and makes you dinner=winner 🙂

    1. I do think that a lot of this stems from fear. Being in love leaves you so vulnerable. It can be amazing but it can also really, really hurt you and that’s scary. But it’s a fear I have to get over.

      You are right about brother-in-law dude. He’s a douche and I know it. I’m done with him. I came to the realization that I don’t even really like him. It was just my ego cause he didn’t want me. And sadly, I did reach out to February guy. I let him know that I was sorry that I messed up. He was nice about it but then let me know that he was dating someone else. I think that’s what pushed me over the edge and made me realize that I have a serious problem. I can’t keep pushing away these good guys.

      1. Don’t give up. Everything happens for a reason. Even if it completely and utterly sucks right now (Yep, I’m cliche hardcore, but for reals).

  3. It sounds like you need to take some time to work on yourself as an individual. You should think about what you really want and the things that truly are deal breakers. Also, work on your confidence. It seems like there may be some lingering insecurities and fear that are holding you back. Perhaps you’re afraid that YOU will mess up what could be a good relationship and that’s why you shy away from the “nice” boys.

    Maybe you like nice guys but you want one that’s more aggressive and less clingy. Talk to them. They may be capable of doing those things and they don’t realize that’s what you want. I wouldn’t say it in those words exactly, you could try, “I love when you’re aggressive…” or have a conversation about how both of you are as individuals. That would be a great time to talk about what you both look for in a significant other.

    Just a few tips. Either way, I’d start with YOU.

    Sharing details of your personal life can be hard, especially when it’s painful. There are so many people who will continue to read your posts and find comfort in not being alone in their personal strides and struggles. For that reason, we’ve nominated you for the one lovely blogger award. If you wish to accept please click the link below and follow the instructions. http://bit.ly/1IQ1Nf7

    1. Thank you so much for the nomination. I will try my hardest to respond. It’s just hard with time. But I really appreciate the nomination and will definitely check out the other blogs you nominated.

  4. This has my life story ALL over it. It’s funny how I tried for years to fo everything ‘right’ in relationships, but the one time I intentionally broke every rule (talking about marriage and exes on the first date, for example), it somwhow worked out, and I married him.

    Have grace for yourself. You are intelligent and funny and, in a platonic sort of way, I think you’re a catch 😉

      1. Haha, no worries about the typos. I’m the same way when I’m typing on my phone. Maybe doing all the “wrong” things was what made it right. You let your guard down.

        And thanks! 🙂

  5. I used to have a male friend that was going through the same sort of thing you seem to be describing. He found himself losing interest in the girls he was dating within a couple of months (if not a couple of dates). He just felt like once you knew everything about a person and things started to become even a little like a routine he lost interest and got bored so he would break it off.
    He really didn’t like this and sometimes felt on the outs when he went out with friends who were all well on the marriage train.
    We had a talk one night over many (MANY) drinks and he said he was sick of “going through all these girls”, I told him straight that yeah it possibly doesn’t look good to other people, but screw them because it is none of their business and it wasn’t like he did wrong by these girls or anything, he just broke up with them when the relationship stopped working for him. I also explained to him that one day he would stop going through girls when he found the girl that stuck. I explained that one day he would date a girl and though her annoying habits would drive him mad he wouldn’t immediately jump to the ‘we need to talk’ conversation, a girl that he wouldn’t mind having breakfast/brunch with every Saturday and a girl that he would want to stay over more than one night a week. A couple of years later he did and had his first long term relationship. To be honest I have lost track of him now, but last I heard they were living together.
    I think the same will be true for you 🙂

  6. You’re not alone!!! I feel the same way…. My love life is a mess too. I have never had a boyfriend and I’m in my mid twenties now. I Think I have a bad personality and I don’t often meet guys who show interest in me or can tolerate me at all. In primary school I had nothing, in high school I had mean boys saying to my face they “liked” me whilst the whole class would laugh. In university I met a really cool guy friend and we got on so well but I found he was too clingy to me and I babied him a lot and at the same time, my first job in a restaurant had me crushing on the bar guy. My guy friend ended up telling me he liked me a lot but I said I didn’t like hom that way. The bar guy and I got nowhere either due to my shyness so it’s like I sunk two ships. Needless t say that guy friend does not talk to me anymore. Then at my new work place I met another cool guy but it was just an attraction because we had nothing in common with each other. I also ended up discovering he was a drug dealer too. I Could go on and on but my comment would be massive but overall I regret rejecting my guy friend who I had so much in common with. I guess I got greedy and just wanted talk dark and handsome. Noe that I am older it is better to have someone who is nice, caring and does everything with you, because why would you want a bad boy or someone who can’t act decent or make you feel secure with yourself because In the end is rather have someone who will treat me well but now I probably won’t have the opportunity because I f*ck up so much with guys. Anyway that’s my experience sorry if I’ve gone off on a tangent but I can see myself relating to you.

    1. Hey, Thanks for your comment! You definitely do sound like you’re in the same boat as I am. But at least you realize that you’ve messed up in the past and you seem to have a pretty good grasp on what you do want. I think that’s so important and really the first step. I hate these cliches cause I hear them enough, but the right guy is out there. It’s just sooo, sooo hard to find him. Good luck!

  7. First of all, I want to say just how kick-ass and brave you are for being so honest and putting it all out there. It takes some serious cajones, girl. Secondly, I want to let you know that you are most definitely not alone. I have been in the place you are now SO. MANY. TIMES! In fact, I’m right there now this very second. And it’s weird and awkward and confusing as hell. For me, whenever a guy who is perfectly nice and charming and sweet gives me compliments, takes me out on nice dates and really, truly puts in the effort, who really honestly seems to like me, I think there must be something wrong with him. It’s not that I don’t think I deserve that (or maybe I don’t?), it’s just that I’ve always been with guys who have let me down, who have seemed charming and nice and sweet in the beginning right up to the point when they broke my heart. I have these walls up because as cliché as it sounds, I don’t want to keep getting hurt. It sucks like a vacuum. Which isn’t fair to those who are actually good guys. Ughhhhhh. Dating is just all. of. the. worst! My advice to you, to myself, to all the single ladies out there who are finding themselves in this predicament is to have faith, to not be afraid to put yourself out there and take a chance. Also, don’t just settle with someone because they like you. Know your worth and don’t stop until you find that person who matches that! Love is a crazy, scary, terrifying thing. But it’s also the best thing in the history of ever.

    1. Oh Wendi, you have no idea how much I wish we lived near each other. We could complain about how horrible dating is over a glass (or several) of wine. It really is the worst. And it’s so much harder when you’ve been hurt. Like you, I really do have this wall that I put up and I know it’s not good. That is some great advice you gave and you something I really need to remember.

      And you totally deserve someone just as awesome as yourself! Don’t ever forget that!

      1. Girl you don’t even know how much I would love that! Seriously. I have a lot of girlfriends, but they’re either all married or in a relationship. I love them to death, and am really happy for them (okay, maybe a bit jealous too haha) but they don’t really understand where I’m coming from. I actually went on a date Sunday and oy vey was it awful. He was sweet enough, but just so vanilla. I had to pull conversation from him. It’s just so exhausting! After so many terrible, no-good, very bad dates, a gal begins to lose hope. But that is exactly what we must not do! As hard as that is. Thanks so much, hon! You are amazing x a million kajillion!

        P.S. We really need to plan a girls’ weekend or something soon. Maybe meet in the middle? Haha. xoxo

      2. I feel you! I have only one girlfriend that isn’t married or in a serious relationship. Whenever we go to functions with the whole group, it’s like she’s my date. I want her to find someone but it’s also going to be such a bitter sweet moment for me. Going on date after date is exhausting. There is nothing worse then a date where there is nothing to talk about.

        And OMG I am so for a girls’ weekend. I am in desperate need for a vacation soon anyway!!

      3. For surely! When my last single girlfriend started dating her BF, I was over the moon happy for her! But also a little (or a lot) sad. I lost my wingwoman and fellow guy complainer. But oh my gravy let’s do it! For realsies! I can’t even tell you how much I am in need of a serious vaca! FINALLY meeting my online BFF would be the icing on the proverbial cake. 🙂
        Damn. Now I want cake.

  8. Two thoughts:

    1) Don’t beat yourself up about being too picky or something. If you don’t want to be with a guy for some reason, that’s okay. You don’t owe anybody an explanation. I think relationships and friendships should be easy most of the time. Occasional drama or irritation only. I realize this is subjective, but I do believe it. Life is so much happier when you just say good-bye to people you don’t like–even if you really don’t have that rational of a reason for not liking them! On the flip side, some people can just make life so much happier, and nobody knows exactly what it is about them. Charm, I guess. Pheromones, maybe. Know what I mean?

    2) I encourage using the “If I were going to Europe for two weeks” test. If you were with somebody, but had the opportunity to take a vacation in Europe for a couple of weeks, would you be sad to leave the person for two weeks? Or would you question your commitment to that person now that you’ve got an opportunity to meet some sophisticated European hotties? i.e. when you think about how many other fish there are in the sea, are you content with the fish you already have?

    I don’t think you’re too terribly weird in all this. Getting along with other humans is hard, especially when intimacy and/or sex is on the table. I do think you seem afraid to be alone, but I can tell you that doesn’t necessarily go away just because you’re with someone. When I was single, I was pretty sure I’d die alone. It was not a happy thought. Now I’m married, and I just think, “God, I hope we die simultaneously,” because I am still afraid to die alone, but now ON TOP OF THAT, I don’t want to lose the person I love more than anyone else just so I can suffer for a while before, you guessed it, dying alone anyway (and I don’t want him to suffer my loss if I go first).

    Don’t beat yourself up. And I know you have written about anxiety, so I hope you don’t hate that I’m saying this, but… try to go with the flow on this. Romance isn’t something you wanna force.

    1. Thanks for the comment. Everything you said is so true! I like the European vacation test. To be honest most of the guys I dated, I wouldn’t had a second thought about if I was going away for two weeks. If I find that person where I would genuinely miss him, then he may just be the one lol.

      And I am with on the going with the flow thing. It’s really hard for me to do that sometimes but I know when it comes to dating and love it’s really the best way to go.

  9. I know there’s nothing I can say that will be a magical solution, but to be honest I don’t think you need one! Dating and finding someone to put up with in a relationship-type situation is really difficult. I think you’ve had a slightly worse time of it than me, but I had been seriously worried I had some kind of three-month curse, because that is the maximum time I could stand before stopping dating someone in the past.

    Now I am with someone and the three months is looming (!) and it is the first time I really don’t want it to end, now because I realise that it is the first good relationship I have had in 26 years. It is still early days, but still!

    I’m not going to promise that someone will come along, because that’s nonsense, but I hope that you will meet a man who makes you feel good about yourself and who you’re really crazy about, because you’re lovely and funny and should get to spend lots of time with someone who’s lovely and funny too!

    1. Aww thank you so much for your sweet comment. And congrats on the new guy. It’s such an awesome feeling to find someone that you don’t find yourself getting tired of. That’s a reallyyy good sign.

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