In part two of this series, I give you my top three most awkward hookups of all time. Again, I would like to warn anyone and everyone who thinks this might not be the topic for them. If you had any qualms about reading yesterday’s stories, please stop here. Go no further. This is not for the faint of heart.

 

3. Basement Boy

There was this one time where I would make out with a lot of men. Like lots. I’d get drunk at a party and just pick one out. It was as simple as a head nod towards the door. Women are not that easy.

For a while, I had an arrangement with this guy. I would see him at a party and we would eventually leave together. I actually never had sex with him but he would sleep over (Remember, I never had sex all through college. I use the term “hookup” but that does not mean I had sex with these people.). This was during my awkward “I’m bi” phase that I went through for a hot second. One time he slept over, my friend Steve climbed through my window because my roommates were locked out. It took me a while to realize what was happening and then I just had to scream “No! No! NO!” until he quickly jumped back out the window. I had to then go let my roommates in the front door as they gave me knowing looks. That was awkward.

But, what was more awkward was when I gave him head in the basement of a frat house in the wee hours of the morning. Not only is a basement floor of a frat house not knee worthy, but ew. That’s just gross. In so, so many ways.

2. The Dykey One

This story gets told merely because of how it happened. I was at a party on campus after coming out and being more comfortable with my sexuality. There were very few lesbians on campus and therefore very little to choose from. Being at the same party with a single, attractive lesbian was rare. I noticed the girl from across the room and even though she wasn’t my type, as I think she’s the only girl with extremely short hair I’ve ever gone after, I decided I would give it a shot.

Granted, I was extremely drunk and this was a very crowded party. I was talking to some people for a while and realized I had to go to the bathroom, like really badly. I ran over to the bathroom and am greeted by a huge line. Fuck. I stood there trying to think of another plan but ultimately figured I could wait. By the time I was next, I realized my mistake in waiting. As soon as I got the door locked, I started to pee.

Being inside the bathroom, the damage was minimal. I got my jeans down and to the toilet relatively quickly, but I had to get out of there. I cleaned what I could, took my over shirt and wrapped it around my waist and left the bathroom. Altogether, the damage was minimal. I was about to dart out the door when I thought of the lesbian I had wanted to hit on. I still hadn’t talked to her. Luckily, I ran into my friend (also gay) and informed her that she must keep the dykey girl at the party. I didn’t tell her why but I told her I had to leave and that I’d be right back. She agreed.

I raced home, changed and raced back to the party. I was getting texts from my friend warning me that she thought the girl was going to leave. Luckily (for me? not for her probably), I arrived in time. I started flirting with her and eventually took her home. (I should say that I know I mentioned earlier that women are not that easy and the proof of this is in what happens next.)

To clarify, I also didn’t have sex with this girl. We made out and she slept over. I definitely didn’t push anything further when she immediately asked “What does this mean?” Knowing it meant nothing to me, I figured I shouldn’t be a douche and push those boundaries. But, unfortunately, several weeks later, I brought her back to my house again and got a “What are we now?” question so I clearly hadn’t learned my lesson the first time. Awkward sauce… all around.

I ended up taking her on a coffee date just so that I didn’t feel like a complete asshole. Coffee has never seen more awkwardness.

1. Kleenex

Tom sent me this topic knowing that I would have to tell this story. We all know that she has to be number one. Kleenex (aka the crier) was the first girl I ever made out with. I was at a place called the Slunt (yeah, that’s what we called it and you might guess that it was a basement apartment where drinking frequently took place), where I was frequently senior year, and junior year for that matter, and I had invited this girl over. She and I had flirted at the bar the night before and I got her number. A lot of drinking went on at the Slunt and therefore, it didn’t take long for us to start making out in Tyler‘s room (sorry Tyler). I would feel really bad about this except that she then had a total freakout and left.

Obviously, this should be a read flag but I’m not one for nationalism. I continue in my pursuit of this girl. Unlike some of the other girls I had gone after that last year in college, I actually really liked this girl…. which was so so so unfortunate.

What makes this story great is that I never learned my lesson. The next time I saw her out, I flirted and asked her back to my house. She came back to my room and after a little bit of making out and foreplay, she just started crying. I can’t explain it. Tears were streaming down her face and I’m thinking, “Oh shit, should I stop?” So, I wrapped her up in my arms and let her cry it out. Until, obviously, she freaked out and left.

The next party I saw her at, I figured maybe I wouldn’t have a repeat of this little scenario. But, of course, I started drinking and flirting and somehow, I end up in the bathroom with her. I pick her up and put her on the counter and we are making out at full force. And just as quickly as it started, it came to an abrupt stop again with the crying.

Yet another time, I take her back to my house and things seem to be going well, then boom, crying.

This lasted for months and months. We eventually started going out to dinner together, as if we were dating, but she would only ever try making out with me while drunk and then she would inevitably cry… and leave.

This lasted for like a year. I never, ever, ever learned my lesson. The girl had to move away for me to finally stop trying. Wonderful. At least I’m persistent!

 

So there you have it. The order might not make the most sense to you but in terms of how awkward I felt each time, that is how they go. Please find it in your hearts to forgive me for revealing this much information. If anyone leaves a comment on this post, I will let you pick the next topic… because, remember, I don’t learn lessons well.