My misadventures in dating, including a Vanilla Ice concert, an ill-advised date at Taco Bell and my car getting stolen.
A few weeks ago, my friend Paul and I launched a new web project, called Wow, My Date Sucked! It has two parts: One, a place to read and share stories about terrible dates, and two, an online video series based on some of those stories.
As I’ve been reading the stories that people have started submitting, it’s inescapably led to me thinking back on my own dating past… and many of the disasters therein.
I rarely do personal lists like this anymore (although it’s the second-most popular archive category that people click on); let’s call this a groove, slightly transformed, just a bit of a break from the norm.
In honor of Wow, My Date Sucked!, here are the 11 worst dates of my life, presented in chronological order.
1 | The Vanilla Ice Concert (Winter 1991)
I was an 11-year-old 6th grader. My girlfriend was an older woman — a 12-year-old 7th grade cougar. (With whom I’m Facebook friends; of all the girls on this list, she’s most likely to read it.)
In 1991, at least at my middle school, there were three albums that everyone had to have. One: MC Hammer’s Please Hammer Don’t Hurt ‘Em. Two: The Simpsons Sing The Blues. And three: Vanilla Ice’s To The Extreme.
And we wonder why, a year later, the world was so rabidly accepting of the grunge era.
Anyway, my girlfriend and I decided to go on a big date: We were going to go see Vanilla Ice. It was the first concert of my life and the first real date of my life.
Frankly, from the little bits I can recall, the concert wasn’t that bad. Her mom took us there and sat, bored, while we stood, cheered and rapped along… Vanilla Ice performed all his hits… briefly addressed his controversy of the moment (it had just gone “viral” that he was actually a rich suburban kid)… and, as expected, he rocked the mic akin to a vandal.
But I’ve had to live the rest of my life with a deep, dark skeleton in my closet: My first date was to a Vanilla Ice concert. NON ironically. It’s some kind of miracle I was able to bounce back from that.
2 | My Brand New Job (Spring 1995)
Near the end of my sophomore year of high school, I got myself a summer job. I would work at an overpriced sporting goods store at the most popular mall in the greater Cleveland area. It was (and still is) called Beachwood Place and, back in ’95, it was THE spot for Eddie Bauer, CD singles, Timberland, and those white NCAA hats where the school nickname was between two lines in all capital letters and then the school name was below it. My salary: Minimum wage at the time, $4.25 an hour.
My third day on the job was a Saturday, working 6 pm until close, at 9:15 (mmm hmm, how good that $13.81 before taxes would feel in my pocket). This timing presented a problem: A very nice girl named Melissa had invited me to a formal that evening. I couldn’t go about taking time off in my first week at the job… but, with such short notice, I couldn’t cancel on her either.
So I conceived a brilliant plan: Melissa and I would go out to dinner, then I’d go to work (carrying my suit with me, stuffed into my K-Swiss duffel bag), change in the mall, and have my mom pick me up and drive me straight to the dance. I’d meet her there no later than 9:45… still ample time to dance to This Is How We Do It.
Well… somehow the communication got a little screwed up. (And, due to my nature as a rabid over-appeaser, I no doubt caused the screw up — I’m sure I told her there was a chance I’d get done early, that I’d probably be there right at 9, etc.) This was long before everyone had cell phones, so I couldn’t keep in text communication with her to let her know I was “doing everything in my power” to get there ASAP.
By the time I arrived, right around 10, she was furious. It’s one of the only times I’ve ever been screamed at in public… and she just let it rip. As I stood there in my hilariously wrinkled suit (it had spent the night in a duffel bag, after all), her tears were flowing, her friends were trying to calm her down, and I got to hear all about how dumb I’d made her look and how I wasn’t who she thought I was. (More than a decade later I had a momentary impulse to forward her Denny Green’s famous “they were who we thought they were” speech, but I’m guessing she would have absolutely no idea why.)
Eventually, I walked away, deciding I didn’t want to be berated any longer… which, of course, infuriated her even more. I avoided her the rest of the night and, every time I saw her in the future, tried to avoid eye contact or interaction. This was even happening when I would accidentally see her over Thanksgivings well into my 20s.
And, honestly, would still happen if I bumped into her today. I still assume she’s angry at me.
3 | Taco Bell and Errands (Fall 1995)
Months later, the summer’s over, and I keep on working at the sporting goods store. In August, a new girl started working at the store. Her name was Quinn, she was my age but went to a different high school… and we immediately had a good rapport. I finally got my act together enough to ask her on a date — exciting for me because I’d just gotten my driver’s license, and it would be my first driving date.
Well… the car turned out to be a good portion of the downfall. Here’s how the night went, as best I can recall…
7:00 pm – Pick her up. Plan to walk to the door to get her but can’t get the key out of the ignition. (The car wasn’t in park. I was nervous so I’d left it in drive. Having only two weeks of driving experience I didn’t know how to troubleshoot this problem.)
7:15 pm – Following my mom’s orders, I have to put gas in the car. This is my first time doing it solo. I had never had to lift the metal lever that holds the pump before, so I can’t figure out how to get the gas started. The attendants have to help me.
7:40 pm – I tell her I’m hungry. She says she’s not, but I should eat. Not knowing how to speak Girl at the time, I take that at face value and, inexplicably, decide I want Taco Bell.
8:00 pm – We sit at the Taco Bell in South Euclid, Ohio. I eat whatever nonsense I decided to get. She sits across from me, seeming distant.
8:20 pm – I unveil my big plan: We’re going to go to a playground! See, she had once told me that she loved going to playgrounds, so this is my big, brilliant seduction move.
8:40 pm – At the playground, she goes through the motions: I push her on the swing, she does the monkey bars, goes down the slide. At one point we’re both jammed into some little plastic clubhouse and I, ever so suavely, lean over to kiss her. She turns her head so I get her cheek. Had this been an episode of Blind Date a thought bubble would’ve popped up over my head saying, “Yo quiero kiss!” and one over her head saying, “I need to make a run for the border.”
9:30 pm – We’re back in the car. She declares she wants to go to Revco (a drugstore chain that would later be bought by CVS) to buy some stuff. I’m now chauffeuring her around for errands.
10:00 pm – I follow her around the aisles of Revco, bored and completely over it, as she buys something like $50 worth of stuff.
10:20 pm – We mutually decide, in not so many words, to euthanize the date, and I drive her home. I get out to walk her to the door (mercifully able to get the key out of the ignition)… but she runs to the house, saying “Good night!” over her shoulder, before I can even take two steps.
We didn’t see each other much after that — I quit the job a few weeks later for unrelated reasons — but I did bump into her a party a few months later. Where she met, and started dating, a friend of mine. Nice.
4 | The Punch Dancer (Winter 1999)
This is the only time I’ve ever been beat up on a date.
I’m at Northwestern, a sophomore in college. My friend Nathan’s sister is a freshman at Illinois Wesleyan, a college a few hours away. Her sorority formal is that weekend and she asks Nathan to come down and bring three friends to be dates for her friends. He recruits me as one of those friends.
The date was basically fine — the girl (whose name escapes me) was nice and attractive enough. In fact, everything was going pretty damn well… until the dancing.
She had a dancing style unlike any I’d ever encountered. She was a puncher. Literally. As if she’d modeled her dance moves after the endless left-right combo you’d use to beat Don Flamenco in Mike Tyson’s Punch-Out. As we danced (and, keeping with my theme of using period-specific references, I’d guess it was, ironically, to hit me baby one more time)… she was punching. She just kept punching.
I would get closer, and she would not take the hint to pull back the punches. This wasn’t malicious either… it wasn’t a “get back” technique or anything like that. It was just her dance style.
Lefts and rights were flying my way until, finally, I had enough. I was a college sophomore and I was going to dance the way college sophomores dance: creepily and ploddingly rubbing up against her.
I moved in closer. The punches continued. Closer. More punches. Closer. More punches. Finally, I made my big move… and as I swooped up against her, she was already mid-punch. I took the punch right to the stomach… and I felt it. A brief wave of nausea hit me, which I swallowed down, and started laughing. She apologized through laughter.
Although the laughs eased the tension, we stopped dancing at that point, and any forward momentum we’d built up that evening came to an abrupt halt. The night ended with a handshake. When she extended her hand to shake mine, her arm came at me at a nice, normal, non-aggressive speed.
5 | The Bitterest Girl In The World (Winter 2000)
One late February night, my junior year of college I (like any good junior) found myself at a room party in one of the big freshman dorms. There, I met a cute girl (whose name I can honestly say I’ve forgotten). She was a freshman and she was drunk.
After a sloppy conversation (during which she said something about “not having to be alone on Valentine’s Day again”), she threw up. I helped her back to her room, and, the next day, went by to say hi. She was embarrassed… and wasn’t quite as cute or talkative as the night before. We exchanged a few pleasantries and that should’ve been it.
But… I think I’d just watched Can’t Hardly Wait and that had convinced me to seize the moment. (Worst sentence in the history of this blog, right there.)
So I went back to the well. I called her up and invited her to a date party event. I wanted to see which girl was going to show up: The cute version who loved drinkin’ and, despite a few needy tendencies, was somehow charming… or the less cute, more more version.
It turned out to be neither — it was option C. The girl who I picked up for the date party was much less cute, much less talkative… and way, way, way more bitter.
Over the course of the evening she told me she hated sports, the Internet, video games, dating, shrimp, her roommate, college, high school, middle school, and, in one of the most terribly funny moments of my dating life, Jews.
That’s right: I was on a date with a girl who didn’t like Jews. “Wait, wait, wait!” I said, “I’m Jewish, you know.”
“Oh,” she replied, not even close to as embarrassed as she should have been, “Well, I don’t, like, hate Jewish people or anything. I just hate the ones who whine about the Holocaust every two seconds.”
I’m guessing she spent many more Valentine’s Days alone.
6 | ESPN Zone and Rolling Rock (Winter 2001)
Part of my college experience was school buses. Any time there was any kind of group outing, the mode of transportation was a school bus. Even when people were going to formal events they’d cram on a bus.
This story ends on a school bus. It starts innocently enough — Megan, a girl I’d been talking to, invited me to a sorority date party at the ESPN Zone in downtown Chicago. For some reason, before the date, I didn’t eat anything. I have no idea why.
We go to ESPN Zone and she doesn’t want to play any of the games there. She wants to drink. So we go to the bar and proceed to polish off no fewer than 12 Rolling Rocks each. By closing time, we were both extraordinarily drunk. However she had the benefit of dinner.
It hit me when we sat down on the school bus and it started moving. You know that feeling of doom when the alcohol all suddenly hits you at once and you realize you went overboard? I suddenly had the horrible realization that I had a 45-minute bus ride back to campus and, odds are, I wasn’t going to make it.
It was at this time that she decided we should make out. I share this not to brag but rather to embarrass myself further. Because as we kissed right there, in that school bus… and my brain kept thinking, “Oh dear God don’t vomit”… she put her hand up my shirt (?) and onto my stomach.
And at that point in my life, it was one hell of a stomach. By that moment in senior year of college the nonstop eating and drinking lifestyle had yielded a very healthy belly. On the rare occasion that a girl would touch the belly, I would try to fool her by sucking it in.
So that’s what I did. Even with my vomiting threat level at a dangerous tipping point, I clenched my stomach muscles to try to make my belly seem less spherical. And that move… that pushed it over the edge.
I pulled away, leaned over, and proceeded to throw up all over the floor of the school bus. If not for the insulation of drunkenness, this would certainly be the most embarrassing moment of my life.
When we mercifully got back to campus I staggered off the school bus — getting glared at like crazy — and sat down on the curb. Someone handed me a bucket of water, so I went on the bus and did a terribly mediocre job cleaning up the mess I’d made.
That night, Megan swore that she’d never go out with me again, and I swore I’d never drink alcohol again. Only one of those two promises came true.
7 | Hey, Come Watch Me Do Stand-Up (Summer 2003)
My first few years in Los Angeles I didn’t date much. I was doing stand-up comedy almost every night, I didn’t have a very large social circle and online dating hadn’t been de-stigmatized enough yet for me to consider it a viable option.
When I would meet a girl, my strategy, for better or worse, was to try to get her to come watch me perform stand-up. The reasoning behind it was elementary: If she saw me on stage making a room full of people laugh, that would be more than enough to woo her. After all, every woman in history has said that sense of humor is the most important quality in a guy. (And at that point, I was naive enough to believe that.)
There was one big flaw in the plan, though, that I hadn’t counted on: What if I sucked?
During my three-year foray into stand-up, I was pretty good. I was never transcendent, never the guy who people would talk about as the Next Big Thing… but pretty good. I’d own the stage, I had some solid jokes, people would usually laugh — sometimes quite hard. My confidence level, however, was disproportionate. I treated stand-up like a boxer treats a fight: Every time I got on stage, I believed I would kill it and be the greatest of all time.
So I met this particular girl, Veronica, through a friend, and invited her to come watch me perform stand-up that Wednesday night. I had a regular gig performing Wednesdays at a comedy club in Pasadena — so I assumed she’d be doubly impressed. Not only was I making people laugh, but I was a regular — and therefore, unquestionably, hilarious.
She actually showed up. And, naturally, I had one of the worst shows of my career. Sure, the time I got booed off the stage at a college in San Bernardino, California, was worse. As was the time I did a show at the Hollywood Improv and did so poorly that Freddie Prinze Jr. (who was randomly in the crowd) got up and left in the middle. But this was right up there with bad performances. My early jokes didn’t land and I wasn’t good enough to win the crowd back.
After the show, Veronica came up to me to talk. “Are you just starting out?” she asked me. I wasn’t. I’d been doing it for two years. She had one pity drink and we parted ways… for good.
8 | The Alan Greenspan Girl (Fall 2004)
I was at a bar and met a girl. We were talking and, at some point, my last name came up. “Greenspan?” she asked, “Are you related to Alan Greenspan?”
I get that question regularly; usually, I’ll make some folksy half-joke like, “If I was I sure wouldn’t be this poor!” For whatever reason, this time, I said, “Yes, yes I am. He’s my uncle.”
Her jaw hit the floor. “No way!” she told me, “I loooove Alan Greenspan.” This struck me as odd. I mean, sure, as far as Fed chairmen go, he was pretty high profile, but he’s not exactly J-14 centerfold poster material. We kept talking (turned out she was a big debater in high school and college which was when she developed her very, very odd affinity toward Alan Greenspan), I got her number and, about a week later, we went out.
By the sixth time she brought up Alan Greenspan (and the chances of meeting him) on the date, I finally had to clear the air. “I hate to say this,” I said, “But I was just kidding about Alan Greenspan. I’m not really related to him.” “Not even, like, fourth cousins?” she asked. “Nope.”
Our date ended about 15 minutes later when, for the first and only time in my life, the girl I was out with received a phone call that there was a “family emergency.” (Which, on some level, was true — Alan Greenspan wasn’t really a member of my family, so she needed emergency evacuation from the date.)
9 | LCS Game Two (October 12, 2007)
Somewhere around 2006, it became clear to me that I wouldn’t get many chances to see the Cleveland Indians win a World Series in my lifetime. So when they made it to the playoffs in 2007, I was glued to every pitch of every game.
This became a problem when I accidentally told a girl I actually kinda liked that I’d meet her for drinks on Saturday night — the same night as the second game of the ALCS.
Well… it turned out that game went 11 innings and more than five hours. That made me two hours late to the date. And I was so into the game I hadn’t noticed my phone had died… so it was quite a shock when I plugged it back in and saw all the missed calls and texts escalating in anger.
I tried to rectify the situation in the most upstanding, forthright and un-cowardly way possible: Via text message. Surprisingly, I got one back about an hour later. She was fairly understanding, all things considered — but suggested that maybe we don’t bother to reschedule.
I guess that wasn’t a bad date for me necessarily… but I did completely whiff on a date I had been looking forward to. And, even worse, that Indians win just set me up for crushing disappointment about a week later.
10 | The Armpit Hair Incident (Winter 2007)
Hey, a shorter story! I’d been dating a girl for a little while and we had plans to go out to dinner. This was our first real “romantic” date — it was going to be a nice dinner, then back home for some wine and, theoretically, awkward attempts at physical contact.
She picked me up (for some reason I didn’t drive, I sadly can’t remember why). I got in the car and, within 10 seconds, saw something that would change my life. With the short, short sleeves she was wearing, I got a full-on look at the bushy, bushy hair in her armpit.
It wasn’t a little stubbly. This was weeks, if not months, of neglect. I try ever so hard not to be shallow, but everyone has a few things that just cause a knee-jerk gagging… and for me, a medium-sized lamb’s worth of female armpit hair is a huge one.
It messed up the dinner… I spent the entire time having this internal conversation, “Don’t look at it, don’t look at it, don’t look at it… Ahhhhhh! Why’d you look at it!” Afterward I told her I wasn’t feeling well, so we’d have to skip the wine.
I tried going out with her one more time after that, but I just couldn’t shake the image. So, in the most Seinfeldian moment of my dating life, I ended things with her. It was as if her belly button was saying “Helllooooo” or her name was Mulva.
11 | The Date Where My Car Was Stolen (March 17, 2008)
This last date on the list was the worst of my life. In fact, it was so bad, I’ve got 11 things that went wrong with it.
- I met the girl a few weeks earlier at speed dating. Yes, we went speed dating. Yes, I actually tried to go on a real date with someone I’d met there.
- Even though it was a first date I suggested we go to dinner, defying the classic rule of not going to a meal on a date.
- Her name was Natalie, so I jokingly suggested we go to a restaurant called Natalee Thai. She thought I was serious — and just that lame — so we decided to go there.
- When I scheduled the date for “next Monday” with her, I failed to realize that was St. Patrick’s Day… thereby ruining both of our St. Patty’s plans.
- She was a half hour late to the date.
- When we met up at the restaurant, I realized that the light in the speed dating bar was quite forgiving.
- Most of dinner was spent with her trying to get me to use the ultra-spicy sauce and me not wanting to.
- Our conversation was brutal as we realized we were in diametrically-opposed places in life: I was living the happy single life and she was in HusbandWatch ’08.
- We left the restaurant, gave each other a so-so hug and went our separate ways.
- I decided it was so bad I wasn’t going to go on another date with her ever again. Which was only reinforced when…
- I wandered the streets for 20 minutes looking for my car. I couldn’t find it. I eventually called the police. It wasn’t on the towing logs. I reported it missing. Two days later I got a call from the LAPD. “We found your car in South Central,” they told me, “it was stolen and stripped.”
While I was slogging through an incredibly bad date, someone randomly stole my car. My 2004 Jeep Wrangler was stolen off the streets of Beverly Hills. (I did two lists about this a few years back, 11 Things the Car Thieves Took and 11 Things the Car Thieves Didn’t Take.) The insurance ended up covering the car, but not my laptop that was inside.
I had approximately 200 hours of phone calls over the next week, trying to square away the insurance situation. During that process I was so preoccupied that I never called her again, not even to be polite. I assume she has no idea why (unless it was an inside job, and she got a cut of the chop shop payout).
So there they are. Very long retellings of my 11 worst dates. If this has inspired you to share yours, please check out Wow, My Date Sucked!. Alright! Plug over.