When You Actually Pay Attention, This Is What You’ll Learn From Your Failed Relationships


They say that those who do not study history are doomed to repeat it.  Which is why self-reflection is so important, it allows us to take stock of our mistakes, and take steps to never make them again.  This is especially important when it comes to dating.

At 27 years old I’ve done my share of dating.  And most of it has been pretty good, especially now that I’m a year and a half deep in the most meaningful relationship I’ve ever had.  But as you’re about to read, I’ve fucked up plenty of times in my love life.  And while I don’t necessarily regret any of these mistakes at this point (as they got me where I am today), I want to do my best to not make these mistakes again.

So join me on a trip through memory lane, and read about every mistake I’ve made in my dealings with women.

*Note: I’m organizing this list chronologically by girl.  And I’m including all different types of relationships; from year-long girlfriends to one-night-stands.  Also I’m not including every single girl I’ve dated, just the ones that I think I made mistakes with. 

1. Tara

I Didn’t Know What I Wanted

Tara had the distinction of being the first girl I ever dated.  Overall, we had a great thing.  But the big problem was that she was much more ready for a lifetime commitment than I was.

But I didn’t want to admit that to myself.  When you’re 21 years old, and you’ve only ever kissed a girl one other time before your current girlfriend, you’re hesitant to lose a girl who likes it when you touch her boobs.  So I took a “fake it till I make it” approach and told myself that eventually we’d get on the same page. 

This made for a very rocky, on-and-off again relationship.  She deserved a lot better.  She deserved someone who was head-over-heels in love with her.

I Said I Wanted To Go On A Break After She Came to Visit Me In NYC

During our relationship I spent a summer interning in New York City.  One weekend that she spent every penny of her graduation money to come visit me and book a hotel room for us to stay in.  It was an amazing weekend for both of us. 

About two weeks later I told her that I wanted to go on a break, so I could have fun without any commitments while I was in NYC. 

To this day I still feel like a dick about that.  But wait, it gets better…

I Got Back Together With Her, and Broke Up With Her a Week Later

When I got back from NYC, I had every intention of ending things with her officially.  But when I saw her again, there was still a spark between us.  So we got back together… I broke up with her again a week later.

That was when we finally ended for good.  I won’t say we never had sex again after that, but that’s another story. 

2. Polly

I Made Out with Her the Night She Broke Up with Her Boyfriend

Even though I really liked her and I knew she had feelings for me, I shouldn’t have hooked up with her hours after she broke up with her boyfriend.  When she came onto me, I should’ve stopped her.  Even if she didn’t show it, her head and feelings were probably all over the place.  She needed a friend more than anything else that night.  And I should’ve been that for her.  Maybe if I had, we would still be friends today.

I Got Mad at Her When She Chose Him Over Me

When she told me that she was getting back with her boyfriend I was furious.  And I didn’t really hide my anger from her.  I made her feel bad for choosing him over me.

But what the hell was I expecting?  She knew I wanted to move to New York, and that I was planning on leaving before the year was over.  Any relationship we could’ve had would’ve come with a fast approaching expiration date.  It was selfish (and kind of arrogant) of me to expect her to throw away a serious long-term relationship for a fling with me that would’ve last three months at the most.

3. Olivia

I Focused Too Much On my Work

This was probably the big over-arching problem in our brief relationship.  I was determined to turn my internship into a job, so much so that I didn’t focus much on anything else.  Not even the awesome girl that I was seeing.

I Always Waited For Her to Contact Me First 

Right when I started my internship I witnessed one of the other interns get chewed out for constantly texting his girlfriend.  I didn’t want that to happen to me, so I decided to never text her first if it was during the day.  My reasoning was that if she texted, messaged, or gchatted me first, then if I responded I was just being polite.  But if I contacted her first, then I was slacking on my job.

I Didn’t Visit Her Again

At the time she was going to school in Pittsburg, and I was living in New York.  One week she suggested that I come visit her.  So I hopped on the Megabus and went to Pittsburg for the weekend.  This was both the beginning and the high point in our romantic relationship.  Since we were never exclusive, that weekend was the only time she was mine and no one else’s.  And I could’ve had that again.  But I chose not to.

She had asked me a couple different times to visit her again.  But I didn’t because I wanted to save my money.  I didn’t have a paying job at the time and I was living off my savings.  So after I made that trip I thought that the only way I could survive in New York long enough to turn my internship into a job was to basically spend no money on things that weren’t rent and food.  I assured her that I would be able to afford to visit her again after Christmas, after I got a deposit from The Bank of Grandma. 

But our relationship didn’t last that long.

When I look back, I realize that I could’ve easily made that trip again.  I could’ve spent another $150 to visit her.  And I still would’ve had more than enough to survive and pay rent. 

I Worried Too Much About What She Thought of Me

I feel like I was constantly trying to be the person I thought she wanted me to be.  It wasn’t like I was deliberately acting in away that was contradictory to my personality, beliefs, or values.  I’d like to believe it was more subtle than that.  It was more things like I would act as if I really loved her favorite bands when I only thought they were ok.  Or when we were talking about something that she was really passionate about, I would try to seem like I knew more about it than I did, just so I wouldn’t seem stupid.

The sad thing is that she never pressured me to be someone that I’m not or to agree with her on everything.  I did that all myself, simply because I didn’t want to disappoint her.

I Worried Too Much about Coming On Too Strong 

Near the end of the weekend we spent together, we had the “what do you want this to be” talk.  She said that she wanted to keep it casual for a while.  I was 100% ready to make it official, but I said that I agreed with her so I wouldn’t lose her.

That conversation, plus the fact that she was the most free-spirited person I had ever met, made me really nervous about coming on too strong.  I felt like if I acted too relationship-y that I would scare her off.  And since I really, REALLY didn’t want to do that, I overcompensated. 

Whenever we would talk I didn’t do anything flirty, unless she did first.  I never sent her a sexy text message.  I never called or texted just to say that I was thinking about her (even though most of the time I was).  This was another reason why I rarely contacted her first.  I essentially didn’t act like we were dating.  I held back a lot of the affection that I wanted to give her.  I didn’t realize that she would’ve responded more if I hadn’t held back.

I Took Her For Granted

At that point in my life I hadn’t had much luck in the dating department.  But with Olivia, I felt like it was finally my turn, that I had finally found a girl who was right for me.  I really felt like after all the years of rejection I had suffered, that I deserved to have her.  I felt like the universe was finally giving me girl I felt it owed me, and that we were meant to be together.

I was very, very, very wrong.

4. Sydney

I Never Considered Actually Dating Her

The night we met, we were making out before we knew each other’s names.  We went on one date after that.  To make a long story short we became friends with benefits.  And this worked just fine for both of us.  We enjoyed ourselves, and neither one of us felt like we were taking advantage of the other. 

But when I look back, I can’t help but wonder whether or not we could’ve been more.  I don’t think it would’ve been totally implausible.  We were obviously attracted physically, and our post-coitus pillow-talk got fairly personal all things considered. 

The thing is, at the time I never considered it.  We both knew what our relationship was.  So I never imagined it could be anything else.  I don’t know if we would’ve made a good couple or not.  And now I’ll never know.

I Ended Things With Her Via Text Message

She rightfully called me out on this after I said we should stop hooking up.  It doesn’t matter what your relationship with a girl is, if you need to break it off, don’t do it via text.  Overall she was cool with it.  But still I should’ve at least called her.  She deserved that.

5. Jeanette

I Treated Her Too Much Like a One-Night Stand

Essentially that’s all it was.  We met at a bar in the Lower East Side, hooked up, and I never saw her again.  But as I look back on that night, I realized that she was someone I would’ve really liked to date.  She was fun, smart, sexy, and we seemed like we had a lot of similar interests.

The problem was, during all my interactions with her, my mind was on one thing.  Can you guess what that one thing was?  I’ll give you a clue; it rhymes with sex.

I really wanted to sleep with her.  A lot.  But we didn’t have sex that night, we did the whole “everything but”.  Probably because she didn’t want to drunkenly sleep with a guy she had just met, you know like a responsible human being.

The next morning we talked about hanging out again.  We even made tentative plans.  But when I texted her to follow up she never responded to me again.  It took me a really long time to realize that it was probably because when we were talking about getting together, my mind was still in “I want to bang this girl” mode.  And she could probably smell that a mile away.  Girls are good at picking that up.  And given that I can’t really blame her for blowing me off.

I Drunkenly Booty Called Her A Couple Times

I bet you can guess how well that went.

6. Harrison

I Wasn’t Willing To Wait For Her 

She was the first girl I ever met on Tinder.  When we first went out I had no idea what to expect.  But I was pleasantly surprised we actually hit it off well.  We even went out a few times after that. 

Every time we went out I had a lot of fun.  We could talk for hours, we laughed a lot, and most of our dates ended with a quality make out session.  All in all, it looked like it could’ve been something good.

But after about four dates, I stopped calling her.  I never contacted her again.  After that fourth date I just stopped being interested in her.  I told myself that it was because I just wasn’t crazy about her, and that I didn’t think we could work out in the long run.  And maybe that was true.

When I look back I can’t help but wonder, did I lose interest because I really didn’t think we would work out?  Or did I stop calling her because she hadn’t slept with me yet, and didn’t look like she was going to any time soon?

I was going through the longest dry spell of my life when we started dating.  I was getting dangerously close to going a year without having sex.  So I wasn’t really in the mood to date a girl who wanted to wait.

But what if I had been willing to wait a little longer?  Would we have kept dating?  Would we have found love? These are questions that I don’t have the answers to.  And I probably never will.

7. Jenny

I Treated Her as Someone I Only Wanted to Hook Up With

Our courtship began, as so many do, on Tinder.  After messaging for a few days we met up at a club in the Lower East Side.  We hit it off pretty well.  We had some drinks, and we talked about how happy we were that we were both better looking IRL than on our Tinder profiles.

*Pro Tip: If a girl straight up tells you that you are hotter than you looked on Tinder, you’re doing something right.

Eventually we got back to her place and fooled around for a while.  The next morning we exchanged numbers and went our separate ways.  It was at this moment that I decided that Tinder was pretty cool.

We hung out a few times after that.  Our dates usually had a consistent pattern.  We’d meet for a couple drinks, talk for a while, and then we’d go back to my place and for some sexy time. 

Now I know that this doesn’t sound too bad, and it definitely wasn’t.  After all, I got to wake up to a half-naked girl on a regular basis.  A beautiful, half-naked girl who, in retrospect, seemed like she was kind of into me.

But, like the chivalrous gentleman I was at the time, whenever we would hang out my mind was on what would come at the end of the night.  Everything I said and did during those times was in an effort to get her back to my place.

Whenever we got together I was always thinking to myself “how can I speed this along?  Because I would really like to feel her tits again.”

I still don’t know what was going through her mind throughout the time we were hanging out.  I don’t know exactly what her feelings were towards me.  Whether she legitimately liked me, or if she saw me the way I saw her, as a friend with benefits with a strong emphasis on the benefits.  But this is one of the many times where I wonder if I wasn’t so focused on sex, that maybe we could’ve had more.

I Came On Too Strong – Eventually I realized that this was a girl that I should try to pursue a relationship with.  So naturally, I tried WAY too hard.  I texted her all the time, I asked her out every week, made myself way to available, and also I just wouldn’t take the hint.

Eventually she started blowing me off every time I asked her out.  She did this multiple times but I kept trying.  It’s only in retrospect that I realize that I must’ve seemed so freaking desperate… which I was.

I Tried to Booty Call Her Again – It was Valentines Day.  We hadn’t spoken in about eight months.  I asked her out for a drink, at around midnight.  I had clearly matured a lot since I last saw her.

8. Arielle

I Went Out With Her Too Soon After We Met

We met one Friday evening at a mutual friends birthday party.  We hit it off, danced, made out, and exchanged numbers at the end of the night.  The next day I called her and asked her out.  We made plans to have dinner on Monday.  Now this might not seem like a problem.  And it wasn’t, except for one thing: I’m an introvert.

The internet is overstuffed with articles about introverts, so I’m sure you know that introverts can only be social for so long before we need to recharge.  The thing about me though, is that I’m part of a subset known as “Extroverted Introverts,” (god that sounds pretentious).  Meaning that I can go out on Saturday night, take body shots and make out with three different strangers, but on Sunday I’ll need to retreat to my apartment and Netflix.  The problem with people like me, is that we often have trouble knowing how much social interaction we can take before crashing. 

And I think this is what happened to me on our date.  When I made plans to go out so soon after we met, I didn’t think it would be a big deal.  But not only was I partying on the Friday night we met, but I had plans on Saturday and Sunday as well.  So by the time our date on Monday came around, my social battery was just about depleted.

The result was that I wasn’t the fun and outgoing guy she made out with.  I was a big ole’ ball of nerves and anxiety.  I was stammering, not making eye contact all the time, and I was so reserved that she said she felt like she was overwhelming me. I’m like Jekyll and Hyde, but instead of my other side being a murderous psychopath, he’s just embarrassingly awkward.

I remember when I asked her out, she said that the next Friday would work for her as well.  But since I was attracted to her, I was excited and didn’t want to wait.  But I wonder how the date would’ve been different if I had given myself time to recharge.  Would it have gone well?  Would we have gone out again?  I don’t know.  But I’d like to think that I would’ve at least been better company.

I’ve messed up a lot when it comes to dating.  But right now I’ve got one hell of an amazing girlfriend who for some reason seems to think I’m worth having around.  So I must’ve done something right.