Illustration by Doug Ross
In every adult’s personal library of memories is a weird little room off the main hall marked “bad dates.” Bristling with curiosities (she vanished for an hour and came back in a different outfit!) and banalities made portentous by context (he ate all the popcorn—loudly), it’s a door best left shut.
This year for Valentine’s Day we gave readers and regular contributors a reason to open it, inviting them to tell us about their worst (and best, though the response on that count was less enthusiastic) dates, lured by the promise of Gabriella Café gift certificates for best happy story and best nightmare story. The winners of our informal office vote are denoted below. As for the rest of the yarns, we’ll let you be the judge as to what these tales say about human nature and Cupid’s impish ways.
—Traci Hukill
Material Girl
About five years ago, I went on a date with a woman who invited me to go see a Madonna concert. I wasn't really into Madonna at all, but I liked the woman, and I pretended to be super cool about it. I picked her up from work and headed to Oakland. My Mustang broke down twice on the way and we ended up needing to take a taxi. When the taxi driver found out that our trip was not very far away, he told us to walk instead. I had a heated argument with him for about 10 minutes until the police came upon the situation. I thought there was a chance I would get arrested, but instead they ordered him to take us. Phew!
Finally get to concert and the girl runs to the seats, disappearing. (I didn't know where they were because she has both tickets.) It took me an hour to find her, all the while listening to crappy Madonna music. The concert ended an hour later (thankfully!).
When we left the show, we went back to my car and my stepfather met us out there to help me get it working again. He told me, in front of her, that I needed a new transmission, he could get one for $1,500 and it would cost me about $900 or more to have someone put it in. As we drive off, my lovely date leaned over and said, “You owe me $250 for those tickets and I need the money before you fix your car.” This was never explained to me before, so it was a date for me and a way for her to get some idiot to pay for those tickets. I never went out with her again, nor did I pay for the tickets.
Anonymous
2 Become 1
I went out for drinks for a friend's birthday. I was VERY recently divorced at the time. So I meet this super cute, really nice, respectful guy and we talked for a majority of the night. At the end of the night he asked for my number and I gave it to him since we really hit it off. So we texted over the next few days and made arrangements to go out for dinner. Sounds perfect, right?
I met him at the restaurant only to find him sitting there with… his girlfriend. I was literally set up for a threesome! I respectfully declined and went and had a drink alone at a nearby bar.
Anonymous
Livin’ La Vida Loca
I finally get a call from a dreamy rockabilly guy I locked eyes with outside a bar. He invites me to dinner downtown. Full of anticipation, we meet on Pacific and he says he knows a “good taco place” up the street. He proceeds to lead me to a dimly lit Mexican place with vinyl seating. It’s dead. And we scurry to take a booth at the edge of the bar. I am quick to order my margarita as my date has arrived via Harley Davison and is wearing a heart melting leather jacket.
As our pitcher of margaritas is placed upon our table, the waiter asks for our order. A starving 23-year-old paying far too much for rent in Santa Cruz, I was prepared for a romantic feast. My date is quick to spew that he is not hungry, but “You should order if you are.” I did. Wanting nothing else in the world but to say, “A plate of enchiladas with carne asada tacos, to start,” I found myself awkwardly saying, “One chicken taco please, gracias”.
The date goes on with me shoving my face full of two-dollar taco and him watching in what, I have come to conclude, was shock. His phone rings abruptly. He answers to the deep voice on the other side that he was out having drinks with a friend and they should stop by. Curious, I say nothing, as he refused eye contact during the call.
Thirty seconds later, a group of leather-wearing men stomped into the bar making shifty eye contact with my date. They skip the vinyl booth and sit at a table in our peripheral vision. Uncomfortable. As he asks me what I do for a living and what kind of music I like, do I know Hank Williams III?, I answer, trying to ignore the fact that his body is turned and eyes driven towards the new table of men sitting adjacent from our homely booth.
Rockabilly then excuses himself to use the “little boys’ room.” I see him land at the adjacent table. Not even halfway to the bathroom. Hand exchanges were made discreetly under the table and my date rejoins me 15 minutes later. I had occupied my waiting time by singing aloud to Shakira's “Loca” playing behind the bar and sessioning chips and salsa.
He says nothing about the fact that the bathroom break was not at all about relieving his bladder and he requests the bill, which was $11. I look longingly at the abandoned half pitcher of margaritas as it grows smaller in the horizon and we exit the restaurant. “Thank you for dinner,” I say out of learned politeness. And he responds, “Oh, no problem.”
Anonymous
What Goes Around Comes Around (****WINNER!****)
I was 19, and my friend had set me up with a sweet, quiet guy she knew from school. We lived in Bakersfield at the time (a perfect setting for a date from hell), and since the County Fair was the only thing that sounded interesting at the time, we went there. It started out well—he bought me some cotton candy, we saw some exhibits—but then when I wanted to go on the rides (my favorite part), he seemed nervous and said he’d had a bad experience once on a ride. It wasn’t until I’d convinced him to give it a try and we’d been belted into a ride called “The Zipper” that he told me that his “bad experience” involved throwing up on a Ferris wheel.
Now, this ride was basically Satan’s version of the Ferris wheel, with a setup of two wheels, a chainsaw-like belt and cage seats that spin upside down and around in a circle, all very fast. Within the first cycle, he was feeling ill. I screamed at the operator to stop the ride, but everyone was already yelling so loud that he couldn’t hear me over the shouts.
Finally, it came—my date began vomiting uncontrollably in Exorcist quantities, all over me and the inside of the cage. At that point we couldn’t stop the cage from spinning, so not only was I thoroughly coated in spew, but the mess whipped out to hit the people in cages directly below and above us as well. It’s possible that there were more hit beyond that, though I didn’t stop to interview them later. Even as the people around us started feeling/smelling it and ALSO screaming at the operator to stop, he didn’t realize there was an issue until we’d made it to the bottom and had some of it actually start flying out of the cage towards him as well. At last, he stopped the ride and we tumbled out, mortified. He was so upset that he ran away. Just literally ditched and ran for the exit of the fair. I tried to clean myself up in the nearby restroom, but it was pretty hopeless (and I was pretty close to losing lunch myself, from the stink). I then realized I was stuck alone at the fair, covered in vomit and no ride home. So I walked. Four miles. In 90 degree heat.
Needless to say, there was no second date. From then on, if someone told me they didn’t want to go on a ride—ANY ride—I believed them.
Sarah
You Give Love A Bad Name
I had gone out with this guy a few times and really liked him. We decided to hang out at his place one night so I could get to know his roommates/best friends over dinner. Everything was going smoothly until his ex called and his roommate handed him the phone and said, “It's your better half.” He took the call in his bedroom and stayed on the phone with her for over an hour while I sat at the dinner table by myself waiting for him to get off the phone and drive me home 
Anonymous
Hello, I Must Be Going
When I was a student at Beverly Hills High way back in the last century I had a reputation for dating every cute girl I could find. “Kessler will go out with anyone who’ll kiss him,” one of my so-called friends once said behind my back. It’s true, what can I say, and what after all is wrong with wanting to kiss as many cute teenage girls as possible? Anyway, one of the cutest girls in my class was Melinda Marx, daughter of Groucho. She had pale skin and dark eyes and thick dark hair and was slim and little, like me, and she seemed kind of shy and sweet, so I asked her out. She lived in Truesdale Estates, a new development in the hills just west of West Hollywood; most of the lots had sleek midcentury modern houses with spectacular views of LA, at night especially, when the lights shone up through the smog and spread in an endless grid all the way to the ocean. It was a Friday night when I went to pick up Melinda. I rang the bell and was invited in and stepped down into the living room where sheets of plate glass revealed the vast city below. Her father, Groucho himself, emerged from another room and she introduced us. He greeted and dismissed me perfunctorily, as if to say Nice to meet you, kid, now get out of here. (He wasn’t smoking a cigar and he didn’t say anything funny, like Pull down your pants, kid, and let’s see if you’ve got any balls.) I think our curfew was midnight. We probably went to dinner and a movie. Our date, alas, was less than memorable. Melinda was not very talkative or witty or interesting or interested in me. In conversation—whatever 16-year-olds could have to say—her cuteness was somehow diminished. Groucho’s daughter, oddly enough, struck me as rather dull. And her dad was decidedly grouchy. We didn’t make out in front of that fabulous view, and I honestly can’t recall if we even kissed.
Stephen Kessler
Queen of Pain
Most people have an ordinary grudge against Sting. It’s the way “Fields of Gold” turns up so regularly on the supermarket Sirius to harsh your shopping buzz. He’s a whipguilt about the state of the world, yet he overpopulates said world with his half-dozen children. But my grudge against Sting is specialized.
Amy was a particularly intellectual looking girl, with gentle, even calf-like bespectacled eyes and with a nice thick pony tail I longed to free from its elastic prison, maybe at the same time I was removing her glasses. She looked like the perfect answer to a long painful drought in the dating department. I had a rich evening in mind: some kind of inexpensive Szechuan dinner on the Mall and then “The Secret Policeman’s Other Ball” at the Nick. That revue had most of the Monty Python gang, with Rowen Atkinson, Alexei Sayle, and a number of other musical comedy types. It was imported from swanky England and therefore sophisticated. At the same time, it was lowbrow enough to stimulate a baser response later in the evening. Or so I hoped.
In the middle of the film, here comes You Know Who, Mr. Sincerity. He plugged in his acoustic guitar and started up his solo and therefore more horrible version of “Roxanne.” I am disgusted with all cheap cynics who claim this moldie-oldie, in which “Roxanne” is urged to “put out the red light,” is the song of a man who is trying to get for free what he is reluctant to pay for. As soon as Sting started singing, Amy stood up bolt upright and walked out of the theater, fast. I followed her. It took me two blocks to catch up.
“What’s wrong?”
She told me, coolly. It turned out that she had a brother, killed in a car accident years before. Maybe it was the stage lighting or the new haircut, but Sting was exactly, but exactly, a dead ringer for the brother. Refusing consolation, she let me walk her home, saying her goodbye from a distance of 20 feet. I couldn’t “Bring On the Night” because it was “Perfect Love Gone Wrong,” so I was “Driven to Tears.” (Or maybe Amy thought I just wanted to “Fill Her
Up.”)
Richard von Busack
Just Like Heaven
My best/most romantic date ever took place in Paris. I was doing a semester abroad and my boyfriend flew out to visit me for a week. We had a romantic three-course dinner cruise down the Seine. The atmosphere was beautiful with the lights sparkling off the water and there was also live music on the boat. It was definitely the most romantic date I’ve ever been on. We had an amazing night.
Anonymous
That’s Amore (***WINNER!***)
September 9, 2006. Rome, Italy. One week after we burnt the Man out in the desert of Black Rock City I was in Rome, headed for a yoga retreat in southern Italy. the yoga teacher, Maria Alfaro, grew up there, and I was to meet her and her family for pranzo, the afternoon meal. After taking the wrong bus and getting a bit lost, her brother Franco came on his bicycle to fetch me. Maria encouraged me to hang out with him, as he was single, and i was soon to be divorced. The three of us ventured out that night to experience La Notte Bianca (the white night), a huge arts and entertainment festival in the city. All the roads were closed to car traffic, the museums were open all night for free, and much like Burning Man, there was a guidebook indicating what you could see and where you could see it. Maria graciously left me and my limited English speaking tour guide at the appointed hour, and we walked alone for a bit. I remember saying to him, “talk to me, even if it's in Italian and I don't understand you!” We came upon a small square with live music playing, and people gathered around on the steps. As we listened to the music, I became aware of a distinct warm feeling on my ankle, and looked down to see a dog peeing on me! I looked up to see the people on the steps pointing and laughing. Well, if that's not an ice breaker, i don't know what is. We spent that night together, and the next day roaming about the city, kissing at all the great landmarks, under just about any tree, and watched the sun set at the Spanish Steps. Hands down, absolutely THE most romantic experience of my life. I married that tour guide. We are currently living in Santa Cruz.
Inga DeAngelo
Come On Baby Light My Fire
For over three weeks, this cute guy used to come into the Starbucks I worked at just to say hi. He obviously liked me (sometimes wouldn't even order a drink) and was super nervous to ask me out. Finally on the Fourth of July he came in and casually asked me where I was watching the fireworks. In a pissy mood, I complained that I get off of work right when the fireworks start so I'll probably be on my way home and miss them. He found his opportunity and asked if I'd like to come to his work (he worked at a waterfront hotel) and watch them from their gazebo by the wharf. Not understanding his intent for a romantic first date, I showed up with all of my co-workers, who destroyed the lobby of his hotel and got him in trouble for the mess they left behind. He didn't come in for coffee for a whole week but he still asked me to marry him a year later, and I said yes.
Anonymous
Just The Two of Us
I think the year is 2005. My buddy Travis just got a job in marketing for the brand new Wells Fargo Arena that opened in Des Moines, Iowa. The Arena was the new home to the Iowa Stars, a farm league hockey team. I convinced Travis to give me tickets to a game on Valentine’s Day Weekend. The day of the game, he called and asked me if I would participate in a chocolate eating contest on the ice between periods. I reluctantly agreed moments before we rushed out the door to the game. We arrived at the game just in time, but decided to eat at the arena restaurant before going to our seats. The waitress kindly gave us balcony seats for dinner so we could watch the game while eating. The location and view made us feel like stars ourselves. At the end of the first period, the announcers requested that all contest participants report to the ice. Travis then escorted us from the restaurant, through the locker room area, to the ice. With the spotlight on us and the other four contestants, we felt as if we were celebrities waiting to be announced to the crowd. With our nerves jumping, we carefully made our way to the middle of the ice and sat at the arranged tables. Next thing I know, the crowd is yelling and we are all face-first in a plate of Hershey kisses. As the buzzer rang, I look to my left and notice my girlfriend attempting to gobble a few more kisses before the officials came around. Apparently the intoxicated gentleman to her left also caught a glimpse of it. He quickly attempted to yell at the officials, calling us cheaters but the officials shrugged off his drunk antics and began to count each plate. To our surprise, my girlfriend and I were unanimous winners. The prizes were nothing to write home about, but the experience and laughter from cheating was priceless. After getting escorted back to our dinner seats, we received a standing ovation from the other diners. Full from chocolate, we got the rest of dinner boxed and decided to check out our ticket seats. The seats were amazing, three rows behind the goalie and not many people in our section at all. Again making us feel like stars! After watching an amazing conclusion to the game, Travis informed us the game just set a new team record for fights in a game. All in all it was a perfect Valentine’s date for my queen in training.
Tariq Lundy
