A Series of Unfortunate Hook-ups: Part II

Two years ago, I spoofed Lemony Snicket’s “Series of Unfortunate Events” for my debut on The Rib by cataloguing the absurd hook-ups that defined my first three semesters of college. While I’ve improved as a writer, and moved on to more sophisticated subjects, a part of me will always feel like I peaked with that first post. From the responses it got, I could tell that I’d tapped into something near universal. The experience of hilariously bad romantic/sexual interactions – particularly the ones where it wasn’t quite clear when exactly they derailed (but oh did they ever) – seemed to be an adolescent rite of passage. As my graduation from college approaches, I have decided to return to my roots with a sequel. To everyone who thought I had grown out of these shenanigans: I didn’t. I apologize to my mother in advance.

Plebeian at the Hilton

By my fourth semester at school, I was deeply dissatisfied with the romantic scene. Along with the growing sensation that I was getting older (and therefore less appealing to my male peers), I grew more adventurous. One evening, while I was home for spring break, I met up with two male friends. One was openly gay, and the other was experimenting with his sexuality. They had been involved with each other once before, and neither was positive what would transpire in their shared hotel room that night. A river of wine later, the three of us took a cab back to the Hilton, and I, despite having lived in New York City my whole life, had never felt so glamorous. Upon arriving, one companion was using the bathroom, and I approached my undecided friend and told him, “Whenever you want me to leave, just text me.”

I said that, but really, I felt like Serena van der Woodsen, and I wanted to have a threesome at the Hilton. It would’ve been a story to tell my grandchildren! Unfortunately (or fortunately, depending on the preferences of my offspring’s children), I received a text sixty seconds later: “Now would be great.” Unwilling to give up, I stumbled 40 blocks and tried to get in the bar across the street from my family’s apartment. I was greeted with, “Excuse me ma’am, do you have an ID?” At that, I dragged my sorry ass home.

Artistic Integrity

Meanwhile, in Providence, I had casually been seeing someone else. He was a creative type, and he felt out of my league. I was eager to keep it going and keep him satisfied – without, of course, having real sex. In the spirit of being spicy, I brought a toy to his room. It was a Tenga brand “Easy Beat Egg” I got for free in Times Square when I was 18, and I had been saving it for a special occasion. Which was not this night.

When I brought it up, he got really freaked out and told me I was being weird. But before I left, he asked if he could see the object in question. This particular item was part of a line featuring labels decorated with Keith Haring’s designs. My partner became egregiously offended by the decay of modern art, and insisted that if his work were ever on something like that, he would kill himself.

He ended it with me a week later to fully pursue other interests. I was left to ponder whether the egg had an expiration date.

Love is Blind, and Kisses Give You Pink Eye

It was Spring Weekend, and everyone on campus was imbibing substances. Chance the Rapper was performing (or so they tell me, I can’t recall) when one of my crushes approached me to dance. As we were kissing, I was thrilled to finally be “bagging” someone I desired so greatly. When I looked into his eyes, they were red, but considering the dense smell of cannabis, I didn’t think twice. Later on, I ran into him again, and I asked, “How high are you?” He replied, “Oh, I don’t smoke. I’m really sick, and I have pink eye.” The next day, I woke up with my eyelids crusted together. To add insult to injury, he didn’t even want to go to second base.

Best Friends, Bad Lovers

At this point, you’ve probably noticed the recurring theme of guys dumping me on my ass, and if you’re extra sharp, you can see how that plays into my insecurities over my barely-there/anything-but-virginity. Consciously, my mind was telling me no, but my subconscious, my subconscious was telling me yes. In pursuit of equality with my sex-having peers, I embarked on a disastrous attempt the summer after my sophomore year. One of my best friends was spending the weekend in my empty apartment, and after we downed an entire bottle of liquor between the two of us, I made him an offer he couldn’t refuse.

Well, actually the first time I propositioned him, he couldn’t quite hear me, and all he said was, “I feel nauseated.” I imagine he meant because of the booze, because upon repeating myself, we had approximately five seconds of very painful intercourse. Then I ran into my bedroom and called my Mom to cry about it.

Not. Exaggerating. At. All.

In the morning, we got eggs and agreed to never f***ing do that again.

A Tale of An Older Man

Junior fall, I was studying abroad in Copenhagen. Across the street from my apartment existed a very pleasant bar with nice candlelight and a decently cute bartender. You don’t fly across an ocean, spend six months in Europe, and not hit on a bartender. A couple weeks into my journey I stopped by, and asked if he wanted to hang out after his shift. He seemed oddly reserved, and then at three in the morning he texted me to clarify that he wasn’t “exactly single,” and was significantly older than I was.

All of my friends insisted it was a polite shutdown, but nonetheless I returned a month after that – hammered out of my mind. The bar was about to close, and all who remained were an old fat man and myself. The bartender was cleaning up the bar, about to close up shop, when he subtly felt me up. It was on like Donkey Kong. Let’s just say that he didn’t feel up the old fat guy, and I didn’t leave when the bar closed. Later, I found out that the bartender had a serious girlfriend, and was 34 years old. I went back a second time.

Bad Friends, Worse Lovers

Returning to Brown, a lot of things were different. Most of my friends were experiencing intense reverse culture shock, and in all the angst of our truncated junior year, I cozied up to one companion in particular. We spent late nights talking, and, although I felt a connection, I was pretty sure it was one-sided. It wasn’t so much a “will they or won’t they” – I was happy just to rest my head on his shoulder once in a while and feel that baseline of sexual tension. Right before the end of the semester, we were celebrating the culmination of finals with an excess of David Bowie tracks and an even greater excess of tequila shots. In one of the most shocking moments in my college career, in the wee hours of the morning, he made a move on me!

I was so taken aback I could hardly focus on the half-naked guy in front of me. The only thing I knew for sure: this had to mean something. All of that time and the connection hadn’t been so one-sided after all! I anxiously awaited my visit back to school for Campus Dance in two weeks. The time came, and finally alone in a room together, I made the move. After five minutes he stopped and said, “I don’t do this kind of thing.” Then he proceeded to get up and announce that he was going to a party. However, I was more than welcome to stay in our mutual friend’s bed if I was tired . . . I guess that’s one way to deal with an unwanted guest.

Out of Window, Out of Mind

Junior year at Brown was a shit-show, so I did my best to recalibrate over the summer. In an effort to follow up on a very sexy New Year’s Eve rendezvous with a friend of a friend, I spent the first two months of summer playing it cool before securing another hangout with him. On a hot night in August, I went over to his place with a bottle of Pinot Noir. He happened to live in a mostly unfurnished apartment, and his bedroom consisted of a lone mattress on a hardwood floor (you’ve got to respect the hardwood, though). When things between us finally escalated to that lonely floor mattress, my partner was first sorely disappointed when I didn’t immediately climax from his superb oral lovemaking skills.

Then, he expressed frustration that I didn’t want to have sex, and threw me some choice one liners, such as, “If you weren’t a virgin you would’ve definitely enjoyed that,” and (in response to me vocalizing my desires), “You don’t know what you’re talking about.” I explained that I was waiting for a committed relationship, to which he replied, “I think you’re making a mistake – that’s unrealistic.” REALLY? IT IS UNREALISTIC THAT I AM GOING TO DATE SOMEONE WITHOUT HAVING PRELIMINARY SEX?

I did call him out on that particular comment, but I spent most of the time just nodding my head and agreeing. It wasn’t until the morning after that I realized what an ass he was. Also, given that his room was bare of all necessities for this encounter, he stood butt naked in front of the open window when it was time to finish, and just ejaculated off the second story. Somewhere below, I imagine an extremely unlucky pedestrian just sighing “not again.”

A Missed (Virgin) Connection

Clearly, the college-aged iteration of me has horrible taste in romantic partners. But was it always this way? To double check, I doubled back to a guy I hadn’t smooched since I was 15. He was smart and a brilliant actor. We used to have major crushes on each other, but I ended up dating this girl instead, and then he and I grew apart so that by the time we kissed nothing ever came of it. I had been trying to reconnect with him for a while to no avail when he invited me to his birthday party. I was pretty excited – if memory serves me, a combination of romantic awkwardness and selective taste basically ensured that he was still a virgin. I don’t have the time here to explain how much pressure that takes off. Anyway, we ended up cuddling by the fire pit, and I went in for the kiss before I left. I even wrapped my leg around his waist like the movies, except he was slighter than me, so our entangled bodies almost fell over in front of his parents’ brownstone. A couple of weeks later, it was my birthday, and we made out again.

In the beginning of July, I drunkenly decided things weren’t going fast enough. With an hour’s heads up I took an Uber to his place. In Brooklyn (dun, dun, dunnnn). Forty-five minutes (and, basically, dollars) later, I arrive at his house. I get in his bed, and he goes straight to get a condom! What the hell??? He said, “Oh, I assumed you were coming over to have sex… I can’t be your boyfriend.” There was nothing left to do but Uber home, with a wallet as empty as my heart.

The ~Sensitive~ Guy

Amidst my summer of not-love, I kept bumping into this younger guy all over the city. Not just in my neighborhood, but in random destinations downtown. I figured it was fate, so I added him on FB and asked him out for drinks. From appearances, he was really into it. I even flaked on him (by total accident), and he called me out for not being good with my phone! When we finally got to meeting up, he asked me all of these deep questions about life and my family. Then he inquired about the father who was conspicuously absent from all of my anecdotes. My dad passed away when I was 15, and, in context, it was pretty obvious. Much like Meatloaf, I will do anything for love, but I won’t share about my dead parent. What was this guy getting at? Against my better instincts, I told him my situation. When he put his arm around me later that night, I thought, “Shit, maybe he’s actually kind.” Could someone actually hear my truth, and not wish they hadn’t brought it up?

Hook, line, and sinker, I went back to his place. We saw each other one more time, and then he ghosted me. I see him around all the time now, and I doubt he even realizes that, from my perspective, he leveraged a very private aspect of my personal pain to get in my pants.

The Over-eager Beaver

You probably have the impression that I am constantly getting rejected. That impression is mostly true. However, there occasionally arises a situation where I have to break it off. After a night of being egged on by my wingman/right-hand-woman, I took a guy home. Except I wasn’t feeling it, so I asked him to leave soon after. A couple of weeks later (on the coldest day of the year), I was throwing a party, and my wingman co-host hybrid invited him – along with like 10 other dudes I was interested in – in a guest list of approximately 150 people. Oh, and I shouldn’t forget to mention that my seventeen-year-old sister was also visiting. Despite all of these factors, and a mildly cold shoulder from yours truly, this guy was the first person to arrive and the last person to leave. That’s not too egregious, but he also went up to each of my housemates and explicitly implied that he would be spending the night. Then he asked how they felt about a fifth roommate… Bro, my sister is my only bedmate tonight. I had to kick him out at two in the morning, after I asked him to take out a bag of leftovers from the night’s festivities a.k.a. the trash.

Extracurricular-cest: Part II

Remember a million years ago, when I hooked up with a guy in the same extracurricular as me, and it ended really badly? I always thought that, of all the lessons I learned in love over the years, that one would stick. Well, wrong again. Lesson unlearned. In the peak of my senior scramble, I locked eyes with a younger member of this same extracurricular. It was a classic situation:

1) Guy and girl start chatting at a party

2) Girl asks guy if he’s available

3) Guy covertly squeezes girl’s ass by a refrigerator

4) Girl goes, “Mama like”

5) They kiss.

I took him to my special spot on campus (the one secret I’m keeping), and thought I was going to treat him to the ride of his life. That is, until I noticed that he had one arm in his jacket, and one sleeve flopping off his other shoulder. I asked him to take it off, and he just looked back at me and giggled. In that moment I knew: he was actually too schwasted to take the jacket off. I made sure he was feeling okay otherwise, got his outerwear back on and walked him home. He insisted that we climb up the fire escape to his dorm room, which was covered in ice, and then he climbed in through his window, where I bid him a platonic and aggravated goodnight. Two weeks later, I saw him at another event, and it was another classic situation:

1) Girl meets guy at party

2) Girl asks if guy is available

3) Guy says no

4) Girl literally runs in opposite direction, hoping that if she goes fast enough, she can travel back in time to a point where this didn’t happen.

I wish I knew how to wrap this up. But I also know that this isn’t really an end – it’s just the beginning of an extremely tumultuous and unaccomplished span of the years of my twenties. Surely, dozens if not hundreds of more unfortunate incidents are headed my way.

I do know that I am so thankful to have found a place like The Rib, where I’ve learned that not only is it okay to express your feelings, but it can also be entertaining to the masses on the internet. I am about as thankful as all of the conquests that are breathing a sigh of relief at not being included in this post. Now that my reign on The Rib is over, I bet you think you dodged a bullet – you did. That is, until I make my own website/start working for something like Reductress. But don’t worry! When the time comes, I’m sure witness protection will take you in.

Yours truly,

Caitlin