The Worst Date Ever: A TSM Roundtable Discussion

Worst Date

Pearls Hilton

My freshman year, I had been sort of seeing this crazy hot lacrosse player named Jack. I liked him, but he was kind of boring and more focused on “school,” and “lacrosse,” and “pledging” than being attentive to me, which was an issue. Still, he was my obvious choice as a semi-formal date, and I was furious devastated when he couldn’t come due to some lacrosse-related obligation. Lucky for him, this was a legitimate excuse, trust me, I checked it out to make sure he wasn’t blowing me off. He had a game earlier that day and didn’t think he would be back in time. Since I’ve never been one to plan anything, I had just assumed he would be able to go, and didn’t bother to ask him until like, a week beforehand, which is why I found myself dateless the Monday before formal.

A bunch of girls in my pledge class were dating boys in the same fraternity and they offered to set me up with one of their boyfriends’ pledge brothers. Desperate and out of options, I agreed to the setup and exchanged a few precursory texts with my date before semi. I didn’t even bother to meet up with him, because I figured the less I knew about him, the better. He was doing me a favor, and beggars couldn’t be choosers. The night of semi, a group of us got ready together and headed over to the boys’ frat house to pregame with our respective dates. I looked super hot and, much to my delight, so did my date.

Aside from his impeccable sense of style, however, he was probably the most boring person alive. I decided to ease any existing tension by getting wasted. During the pregame, I consumed approximately one thousand shots of vodka, and I was so liquored up by the time we left that my date “Brian” had to physically carry me to the bus. Classy. I sobered up on the bus ride over to the venue enough to bring me to the point where I could have recovered had my big not continued to feed me vodka sodas throughout the evening.

In my drunken haze, I began to feel guilty about not having given Brian a chance. I decided to resolve the situation by making out with him in the coat room. Mid-makeout, I realized I was being a huge slut. I second guessed myself and began crying about my indiscretions. (Dating tip: MEN LOVE THIS.) Brian tried to console me, which really just meant we both sat back down on the ground in the coat room, and started making out again.

At some point, I heard someone loudly clearing his/her throat, and I assumed it was just someone who was leaving early, but the throat clearer would NOT stop. I finally looked up to yell at whoever was rudely interrupting my drunken hookup, and I started crying hysterically (again) when I saw that Jack was standing in the doorway, staring at me. Apparently, he had gotten back from his trip and decided to surprise me, which was probably a great gesture, except at this point I was fully committing to my blind date.

Needless to say, Jack stormed off. Brian looked even more confused and irritated, probably because his hookup had been interrupted by tears twice in one night. He left for a little while and returned with two drinks to ease my pain, and entice me to hook up with him, which worked, because I basically couldn’t get off the floor without his assistance.

I fell on my face, trying to walk to the bus back to campus and he picked me up and carried me as if I were a small child. I passed out with my head in his lap on the way back, but none of this stopped me from continuing to party once we got back to the frat house. After I’d had enough vodka, I demanded he find a pledge to drive me back to my dorm, and then refused to let him walk me to my room, fearing he might try to stay over. I thanked him for a “great night” and passed out in my bed.

The next morning, I woke up with an awful hangover and an impression on my face from falling asleep with multiple bracelets on. I removed my jewelry, only to find the word “Pat” written on the inside of my wrist. All of a sudden, the previous night’s blacked out actions started coming back to me. At one point, mid-pregame, my bestie had found a sharpie and told me she was writing my date’s name on the inside of my wrist, because apparently, I couldn’t remember it. Whatever, he looked like a Brian and he responded to it, so I think “Pat” should be the one thanking me.


Before reading this story, you must grasp two concepts:

1. I was in high school, very naïve, and thus incapable of seeing the numerous red flags being thrown in my face.
2. I HATE grand, romantic gestures. A lot of girls love them, but they’re just not my jam at all.

I met the guy at a Sonic one night when I was there with a group of friends. I know, it was doomed from the start. He seemed normal enough and we went to the same high school, so when he asked me out on Facebook (I know), I accepted. Big. Fucking. Mistake.

After he was incredibly awkward and overeager during the obligatory Dad-to-date talk, we set off for what I was told was going to be a nice dinner and a movie. Dinner was at Red Robin (ew). Over a basket of bottomless fries, he told me one of the most ridiculous things I’ve ever heard from a guy, and that’s saying a lot.

Him: So about the movie…
Me: Yeah?
Him: Well I don’t have enough money on my credit card to take you to both dinner AND a movie, so I had to get creative.
Me: So where are we going?
Him: It’s a surprise!

I’m almost convinced I saw my brain in that moment, because my eyes rolled so far to the back of my head. I fucking know how credit cards work, buddy, and the whole “no money” and “Red Robin” business isn’t helping your case at all. Despite my inner monologue, I went along with his “surprise date,” because I was raised to be courteous and polite. When we got back into his car, he whipped out a blindfold. A. BLINDFOLD. Of course I needed to be blindfolded so I didn’t see the super secret location he was taking me to.

Stupidly, I put the blindfold on. Throughout the entire car ride, I jokingly remarked that he was probably taking me to some accomplice who was waiting to smother me with a chloroform rag, then murder me, but I was legitimately terrified that was going to happen. After removing the blindfold, I was on top of an old rock quarry (it’s South Texas, we have a lot of those) in the middle of fucking nowhere, and I was supposed to sit on the hood of his car and talk whilst looking at the stars. I literally wanted to hurl.

He then put on a CD that he proudly stated he made himself. It played, I kid you not, “Kiss the Girl” from The Little Mermaid and “Kiss Me” by Six Pence None the Richer. You can’t make this shit up. He spent the next hour like two inches from my face. I went on staring at the stars, careful not to make any sudden movements to give him the go-ahead for a kiss. It was terrible. I just wanted to go home, but I had no idea where I was and I was completely at the mercy of this weirdo. I saw my out when he said, “Do you want to go into the back seat? My butt hurts!” I immediately declined, and told him I was ready to call it a night.

He made me put the blindfold back on before we drove back, which I did without argument so I could get out of there as fast as humanly possible. He walked me to my door, where I awkwardly said goodbye and slammed the front door in his face. When I told all of my friends about my colossally awful date, one of them said, “I think one of the girls on my swim team went on a date just like that!”

As it turns out, he had taken five other girls on the exact same date. Same Red Robin, same old rock quarry, same cloying mixed CD, everything! So not only did I have to suffer through an entire terrible evening with this guy, it wasn’t even a special terrible evening.

Fleur de Lilly

My roommate conned me into accompanying her to her boyfriend’s date party with the promise of an open bar. Unfortunately, even consuming every drink available wouldn’t have made this set-up okay.

The romantic partner I’d been set up with for the evening was called Tubs. He was a member of a respectable fraternity, and I trusted my sister to set me up with a decent fellow, so I assumed his nickname was some sort of reference to his last name, or a propensity for passing out in bathtubs. I should have been so lucky. We were around the same height, which isn’t tall, especially for a guy, and I’d estimate his weight to have been slightly under 300 pounds. He was also the rare breed of white guy who enjoys to use the word “yo,” and wears his clothes too big. He was essentially my dream guy, is what I’m trying to say.

Tubs was convinced that because we were both Greek and enjoyed drinking, we were soul mates. Spoiler alert: we have that in common with half the campus. This was his jumping off point, and from there, he decided that everything was a mutual point of interest no matter what I said. When I told him I didn’t like baseball, he discussed with me batting averages or something, asking my opinions about different players. When I told him I had just been in Charleston, he told me he was “also from New York.” The only thing I found we had in common was that we happened to be at the same bar that night, but we were soul mates. Tubs was convinced of that.

As he systematically made his way through every drink at the bar, he started getting handsy. I was uncomfortable for two reasons. The first, of course, being that I was repulsed by him. The second being that I was told he had a long-distance girlfriend, who had an obligation pop up, which was the reason I needed to be his last-minute stand-in in the first place. When I mentioned her, he at first vehemently denied her existence, but soon changed his tune, and heavily implied that this sort of thing was permissible in their relationship. I guess he was trying to tell me they were swingers, or something bizarre like that, because instead of seeing my efforts to escape a hookup as discouraging, he very casually, but very seriously suggested we add another couple into the mix. He thought a foursome with the friend who’d invited me and her boyfriend would be a fun way to end our night. Tempting, but I passed.

You’d think at this point any guy would have realized how awkward the situation was, but not Tubs. On the ride back to campus, he chose the bitch seat on the bus. His size made it wildly uncomfortable to share a seat with him, and I was forced to go to second base with the window to avoid first base with him, as he tried to MO a dozen different times, despite my turned head and disgusted expression. Once the bus finally arrived back at campus, and I tried to race off, but Tubs removed his backwards cap (revealing what was a mostly bald head), and put it on my head in what I assume he thought was a flirtatious move. He wiped out, and I made my escape, hoping to never see or hear from him again, but unfortunately he contacted me the following week to inform me he’d spent the rest of his night in prison after being arrested for brawling with his pledge brothers. It was the perfect ending to the perfectly nightmarish date.


I remember this loser like it was yesterday. I’d originally spotted him in my best friend’s all-male dorm, which I occasionally visited. We didn’t talk much at first, but exchanged a casual greeting when we crossed each other’s paths. He was exactly my type: he was tall, had broad shoulders, dark hair, dark eyes, and exuded “frat boy asshole.” I was smitten. I was ecstatic when I’d finally gotten the chance to make it clear to him that my friend and I were just friends and were not hooking up, and well, I was available. We started texting.

When he finally asked me out on a double date, I naturally agreed. We’d been talking for awhile by this point, and had hooked up a few times, and the other couple consisted of my sorority sister and best friend, and his fraternity brother. It seemed perfect.

Our dinner was scheduled for St. Patrick’s Day, so my bestie and I got ready together in my dorm, put on our hottest green dresses, spent a casual couple of hours doing our hair, and pregamed with a few shots (gotta loosen up). We only ended up being fifteen minutes late, so the night was set up to be a real success.

The boys had a couple of pledges drive us all to a really chic restaurant downtown. The ride over was kind of awkward because we were all squished in the back of a car, but we made do. I did, however, dock a few points when both boys forgot to open our car doors, forcing us to awkwardly slide out of it in heels.

We sat down at our table, and everyone began to chat. Everyone except for my date. He literally refused to speak. I’m usually very personable and rarely have a difficult time making conversation. It was really difficult to get him to come out of his shell, and honestly, this was pretty unexpected. It’s not like we were strangers or anything. One could even say that we knew each other fairly intimately, if you know what I mean.

Hell bent on making this date a success, I did everything I could to make him any type of interesting, but it was useless. Total brick wall syndrome. He didn’t even talk to his fraternity brother, until the waiter came. As I was about to order, he interrupted to say “She’ll have a salad, no dressing,” and proceeded to be silent the rest of the night. Even though I probably would have ordered something along those lines on my own, I’d never been so appalled.

As soon as we were done eating, I feigned exhaustion so I could go home and cry to my roommate over a bottle of wine before going out for more St. Patty’s Day festivities. Being the lady that I am, I thanked him for the date, even though I couldn’t have felt less thankful. He didn’t even walk me to the door.

Needless to say, he did not get an invitation to formal that semester.

Hot Piece

Our first date should have been our last. The guy, whom we’ll call Jason, because his name was Jason, was a solid 5 with no sense of humor. He was clearly batting way out of his league, but I have both major self-esteem issues and a love for attention, so a boring, average Joe who brought nothing to the table, but allowed me to dominate the conversation, occasionally piping in about how pretty I am, was the recipe for the perfect storm.

Despite some weird text messages, when he asked for a picture (of my “gorgeous smile” as he clarified, sensing my discomfort), as a reward for winning the thumb war he’d initiated on our first date, I agreed to see him again. I can only attribute my poor decision to the fact that I wanted more “practice” dating so I’d be an “expert” at it by the time someone I was actually interested in came along.

He insisted on picking me up to take me to dinner. Call me a skeptic, a liberal, or just fucking smart, but I was a little uneasy with this. I didn’t really think this nerd would kidnap me, bring me to some Texas farm, have his way with me, and leave me to the mutant creature that is born when a donkey and an alpaca mate, but serial killers and rapists don’t normally fit the tall, dark, and handsome profile, so it was possible. In order to avoid my potential murder and/or fetish sex in a remote location, I asked him a simple question.

“Where are we going tonight?”

I just wanted to have someplace to tell my friends I’d be, in case I turned up missing, although, realistically, if I’d gone missing, I’d already be missing, and knowing where I was supposed to be would be of little help. He shadily avoided my question three times before answering, so I promised my friends I’d check in “dead,” “alive, penetrated against my will, and slightly mangled,” or “alive and well,” in a few hours.

For a moment, as I was getting ready, the thought occurred to me that maybe he’d insisted on picking me up rather than meeting me because he was going to surprise me with flowers. I quickly brushed the thought away because that was crazy. This was only our second date, and third encounter. There was no way he didn’t know enough to know that it was way too soon to stop playing it cool, and that romance would be construed as creepy this early on. Everyone knows that. EVERYONE. Except for Jason. I awkwardly invited him and his premature flowers into my home, and put them into a plastic sorority cup, because I’m classy.

After receiving flowers, having my door opened for me as if to tell my neighbors “HEY, WE’RE ON A DATE!” and being told I was soooooo pretty too many times for comfort, Jason finally stopped doing all the shit the hot guys do in romantic comedies to make girls fall in love. The “gentleman” gig was up when we were at dinner.

I prefer to keep an air of anonymity about my job when I meet new guys, mostly because I don’t want them to know I’m a manipulative, gold-digging bitch to read what I’ve written, and make false assumptions about me. On our first date, I’d told Jason I’d give him the name of the site I wrote for if I got to know him better, but on our second date, he made sure I knew that wasn’t necessary, as he’d googled me and knew exactly what I did. CREEP! He then pulled up a column of mine he’d familiarized himself with. It had been published 387 days prior to our date.

“I don’t know why you even agreed to this date with me.” Neither do I. “I don’t fit any of the qualifiers on this, uhhh, checklist you have. My eyes are brown, I’m under 6 foot, I’m Mormon…” Hmmm, you’re on a date with a girl who is clearly out of your league, and you are purposely pointing out the ways you fall short of what she wants. Seems smart. And hold the fucking phone, did you just say you’re Mormon?!

I politely explained that this was my job, and he either had to grow a nutsack and get over it or get over me. I didn’t even bother pointing out how creepy it was that he literally must have spent at least an hour, probably more, researching me to find a column that was over a year old at the time. I mean, I probably would have done the same thing had the roles been reversed, but I would have suffered in silence, and then make him pay for it once we were in love, like a normal person. Plus, I was too annoyed to be creeped out.

He continued to give me a hard time about my job for the remainder of the date, which I thought would end after dinner, but he insisted on taking me to some Honkey Tonk bar that made me want to commit suicide upon entrance. He asked what I thought of the place. Rather than tell him I would have actually preferred he took me the estranged farm where he left me to the donkpaca that I’d originally feared, I told him that a bar with a pool table and literally one other person who was some cowboy-looking motherfucker in the corner was “different than any place I’d ever seen,” because “we definitely don’t have anything like it in New York City.” He took this as his cue to tell me to move back if I didn’t like it. Being about five vodka sodas deep, and gaining a new appreciation for Patti Stanger’s two drink rule, I started to cry. On our date. I cried on our date. So that happened.

After driving me home, the goober walked me to the door and ASKED me for a kiss. I don’t know if there’s a bigger boner move than asking for a kiss. I didn’t know what to say, and when he tried to lean in, I pulled away, and he followed my lean until I was bent so far back that I looked like a boomerang, and literally had to put my hand on his chest and say “no thank you.” He attempted to entice me with a bottle of vodka he’d apprently picked up, because…I don’t know, a bottle of wine would have been too normal for a nightcap? His assumption was the literal only thing that could have turned me off from him further, and I told him so. I closed my door and ignored his “I had a great time tonight” text, because if we were on the same date, it was bullshit.

He still texted me three days later, but I maintain that I am probably going to die alone.


Be sure to look out for our next Roundtable discussion. Until next time, betches.

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