Awful First Dates

by Sarah Wexler

  I decided to cancel—our first conversation was me waking him up like I was his mom!

  A RASH DECISION

  We met for dinner and drinks, and I mentioned that I liked his beard; he told me he had a terrible neck rash and couldn't shave. We had a few glasses of wine, and as he got drunker, it came out that he was not only unemployed but was also homeless, couch-surfing, and still messing around with an ex-girlfriend whom he bitterly rambled on about for way too long. At the end of the night, he asked me to go "home" with him! Not excited at the prospect of waking up wedged into a couch next to a guy with a skin rash, I politely declined. Then he offered to come stay over at my house—and infect my pillows? No thank you.

  DISHONORABLE DATE

  As he drove me home, he told me how he had recently gotten out of the army. He (an enlisted soldier) was friends with a female officer, but another officer was jealous and so "made up a story" about how my date and this female officer were sleeping together (which can get you a dishonorable discharge pretty fast), so instead of going through that, he "pretended to be depressed" so he could get out for medical reasons instead of bad behavior.

  PROZAC NATION

  We agreed on meeting up after work for dinner and drinks. As I eyed the menu, I noticed that he hadn't touched his menu and asked, "What are you ordering for dinner?" He said, "Nothing. I've already eaten." Okayyy. Then I asked, "What are you drinking?" "Oh, I don't drink," he said. We'd been at the table fewer than five minutes. "I'm on Prozac because I'm absolutely crazy, and Prozac doesn't mix with alcohol."

  SON OF DEBBIE DOWNER

  I met this cute guy for a blind date at a coffee shop. From the beginning, his expression was mopey, and as soon as I sat down, he began methodically listing off every terrible thing that had happened to him in his life. His car got broken into, his band's equipment got stolen another time, his cat got run over by his mom when she came home drunk one night. I tried to look sympathetic, but I realized the only thing I was contributing to our conversation was, "Oh no, how terrible!" My breaking point with his sob stories was when he started describing how he once got kicked in the junk with another kid's cleat so now only has one testicle. I thanked him for the fun time and left.

  THAT’S SOME HEAVY BAGGAGE

  On our first date, he talked a lot about his ex-wife (except he'd sometimes refer to her as his wife), about how she left him, and his subsequent suicide attempts. When he said that, I touched his arm and said I was sorry. All of a sudden, he froze. He closed his eyes and started taking these big deep breaths. I asked if he was okay, and he said that he was so emotional because it had been five years since another human being had touched him.

  THIS DATE BLOWS

  I met a guy at a very noisy bar, so I had no idea that he talked that loudly in everyday life. On our date, sitting at a coffee shop, he yelled through the entire conversation, which was embarrassing enough...until he decided to tell a story about how when he was fourteen, he was flexible enough to give himself oral pleasure. I turned bright red and tried to change the subject, but he went on about how he used to do this all the time until he was no longer flexible enough to reach. The people around us looked like they were trying not to laugh...or vomit.

  THE BOOKWORM

  I'm an avid reader so I decided to ask him about his favorite novel. His response was, "I haven't read anything in a while. Well, maybe in high school?...Nope. Hmmm, maybe in middle school?...Nope. I may have read something in elementary school. Come to think of it, I have never read an entire book in my life."

  FAMILY TIES

  Things were going well—conversation was easy and we had a lot in common. I didn't realize how much, though, until he told me his rather unusual last name, and I asked him if he knew a woman in the city who had the same last name—who turned out to be his sister. And my gynecologist. Who recently treated me for herpes.

  TOO-HONEST ABE

  After a dinner heavy on pork belly, we went to a tequila bar, and two drinks in, my stomach started doing flips. I politely told my date that I wasn't feeling well (not mentioning specifics) and needed to head home. Ever the empathetic guy, he told me not to worry—he'd had diarrhea while on dates before.

  HE’S A SAMANTHA

  MY DATE: So I have to ask you something. It's extremely important.

  ME: Okay.

  MY DATE: When you go to Bloomingdale's, where is the first place you head?

  ME: The second floor, I guess. Women's clothing.

  MY DATE: Me too! I love women's fashion. I used to watch Sex and the City just to see all the clothes and shoes, like Manolo Blahniks. Do you have any Manolos?

  THE PUPPET MASTER

  He said he'd cook me dinner at his place. The apartment was sparse and not really decorated, like a typical guy's apartment, but the dining room walls were covered in ceramic Mardi Gras masks, and a marionette of a clown.

  I didn't even know what to say, so I asked why he had a marionette. "It was really expensive, but worth it," he said, "because I like to put on puppet shows."

  THE AMATEUR DERMATOLOGIST

  He told me he didn't really like his job, so I asked what his dream job would be. "I'd like to take care of people, to make them feel better," he said. I thought that might mean becoming a personal trainer or a nurse. "Maybe," he said, "but I really just like to help people feel good by taking care of their skin. Suppose you had a pimple on your face. I would like to pop it for you."

  Awful First Dates: Hollywood Dispatch

  "It's very odd to start dating after being married for a long time, and this was one of my first dates since the divorce from my husband. My date might have only been six or seven years older than me, but my kids see me as very youthful. He came to the door to take me out. My daughter was teeny tiny at the time, and she announced, 'Mom, he is too old for you' right in front of him."

  —Andie MacDowell

  Chapter 8

  MR. MALADJUSTED

  This is the type of man who makes you think you've gone crazy, even though he's the one acting a fool. He runs over animals and keeps driving; he says things that are completely inappropriate; in the middle of a fancy restaurant, he starts eating soup with his hands. I mean, who does that? These guys. Faced with this kind of date, you might worry you've hallucinated his behavior, that no one could seriously be that clueless. Or wonder if Ashton Kutcher is punk'ing you. Or figure that at least this will make a good story, if anyone will believe it. Or you start making excuses for your date: maybe he came from an "anytime is naked time" home, or he has undiagnosed Asperger's, or he's just a free spirit who doesn't feel constrained by societal norms, and good for him. Still, his wack-a-doodle behavior is too much to handle.

  Dating should be about enjoying your time with a person you respect and are attracted to—not about rehabilitating a man who acts like he was raised by wolves and is only now entering civilization. You're looking for a partner, not Encino Man. So if he's lacking the kind of basic skills the rest of us mastered in elementary school, make a dash for the door. The good news is that he's probably too clueless about social cues to even know he's being ditched.

  BLOODY PERFECT

  He was fifteen minutes late, even though he'd told me on the phone he only lived two blocks from the restaurant. When he finally showed up, we shook hands and he said, "I'm sorry about my face." Noting nothing of offense, I asked why. He pointed out a teeny-tiny scar above his lip. He told me he'd gotten so drunk a month before that he woke up in his apartment covered in dried blood with a paper towel stuck to his face and never found out what happened. "The worst part is, that's not even the first time I woke up bloody this year," he continued. "In February,

  I woke up with a bloody hand at 6:30 a.m. on a subway platform." We hadn't even sat down yet.

  DISAPPEARING ACT

  We were half an hour into a great date. But in the middle of me talking, without him giving any reason (or even looking at his watch), he suddenly jumps off the bar stool and goes, "Okay, nice
meeting you," throws down some cash, and runs off, leaving me sitting there with a nearly full beer. I stayed there to drink it, figuring you just can't hit it off with everyone. But the weirdest part was that when I got home I already had an email from him saying what a nice time he'd had and asking me out again.

  FRO-YO IS A NO-GO

  I was happy to meet my set-up: tall, handsome, and passionate about desserts. He was opening his own frozen yogurt store in a few weeks and suggested we get froyo at a busy competitor's place. Once we got inside, he completely ignored me, hounding the other customers in line about why they chose this place, their flavor preferences, and even handed strangers his business cards, saying they should come to him instead. The only time he talked to me was to analyze my thoughts on their topping offerings.

  THE DAREDEVIL

  He seemed like a pretty responsible, down-to-earth guy: he liked sports, worked in finance, and took me to dinner at TGIFridays. But on the way home, he started showing off by driving down one of the busiest roads in town with no hands on the steering wheel. He really thought he was impressing me, and as we swerved over the center line, he asked, "So, do you like bad boys?"

  CALL HIM KERMIT

  When I showed up for our date, he was reading a book of poetry—and started reading to me aloud. After our drinks, we decided to walk down to a sidewalk sale to do some people watching. There he bought a frog hand-puppet. For the rest of the date, every time he talked, it would be through the puppet. We stopped at a coffee shop and I ordered a drink. Then he held up his puppeted hand and, in a squeaky frog voice, told the barista, "I'd like one too, please!"

  MAGIC MAN

  I was set up with a guy my friend told me was a lawyer, since I'm one also...but it turns out when I asked him about it, he defines himself more by his hobby: being a magician.

  I thought it was kind of odd and didn't know what to say, so I jokingly asked if he was going to cast a spell on me, making me fall in love with him. He got really offended and started lecturing me, his voice rising to the point that other people in the bar were turning around and looking at us, that only witches cast spells.

  NOT-SO-SILENT BOB

  A friend asked if I'd like to be part of a silent date auction, just using my photo and bio, to benefit his nonprofit, and I agreed. A few days later, he sent me an email connecting me with the winner, DJ Valentine (who, as it turns out, had actually never DJ'd). When we met up, I could see why the guy had participated in a silent auction: he talked nonstop, without even pausing to breathe in between thoughts. I asked him about work; he said, "I hate my job because I hate helping people. I want to work with less human interaction." So I asked him about his hobbies outside of work, and he told me, "I do jujitsu in the mornings. Monday and Tuesday morning. Wednesday after work. Thursday and Friday mornings. What I've learned is that you have to cut your nails really short or else they'll rip off." His other major hobby? "Sleeping on the subway. Sometimes I wake up at 7 a.m. and I've just been going back and forth on the train all night." I tried to excuse myself four times, but he wouldn't stop rambling enough for me to even finish saying I needed to head out. Eventually I got so fed up I grabbed my coat and said, "It's late—gotta run!" and bolted out of there.

  MAYBE HE’S IN THE FBI?

  At brunch, the waiter passed me a note with the bill, asking me out. I thought it was kind of ballsy and cute, so I called him and we set up a date to meet for coffee. But once we got there, the guy refused to tell me anything about himself and kept dodging anything I asked. I'd say, "So, how long have you lived here?" and he would say, "Oh, on and off for years." When I asked, "Where are you from?" he said vaguely, "My family has lived all over." He didn't want to tell me his last name, how old he was, or anything else you find out when you're getting to know someone. When I said it was kind of strange that he was hesitant to talk yet he'd asked me out, he told me he'd prefer to "keep the conversation more general, philosophical." Oh, really? Because I'd prefer to end it.

  HE’S PUZZLING

  After a pleasant dinner, the guy seemed a little nerdy and awkward, but I waved it off as endearing. We went back to his apartment and he showed me around. His bedroom was lined with action figures and comic-book posters, which seemed a little immature and more nerdy than I'd expected, but okay. I was hoping we might make out for a little in his bedroom, but he was eager to take me somewhere else: the empty dining room. That is, the room that was empty except for a gigantic framed jigsaw puzzle on the wall, depicting the Simpsons sitting for The Last Supper. Maybe I could also get over that the guy spent a lot of his free time putting together puzzles. But the red velvet rope in front of it, so I didn't get too close like it was a priceless Picasso, put me over the edge.

  HE’S STRIKING OUT

  During dinner he informed me he had been to the dentist that day and was all loopy from the pain meds he'd gotten—which would explain why he kept dribbling his soup. Afterward, we went bowling and he kept trying to stand behind me and "guide" my arm to show me how to get a strike, yet didn't seem to notice that my score was actually better than his. In between frames, he proceeded to tell me about how he makes money despite being unemployed: he scams buyers on eBay by making another account and fake bidding to drive up the price. He was very proud of himself for coming up with that one and kept rambling and doing loopy laughs, which I hope was from the pain medicine.

  BAG IT!

  I went out with a guy who was really hot and tough—he built motorcycles. On the date, he asked me a lot of questions about what countries I'd been to, and I thought it was cool he was so interested in travel. We went back to his apartment and he pulled out a big plastic box the size of a moving trunk. I had no idea what he was going to show me, and it turned out to be his most prized possession: his chip bag collection. The guy was obsessed with collecting potato chip bags from all around the world. He told me that he had the second most in the world, according to Guinness World Records. Trying to feign interest, I asked if I could see some of his favorite ones, but he said they would all inflate if you took the lid off.

  AWFUL FIRST NOT-DATE

  A guy I knew liked me—he followed me around school, always complimented me and tried to touch my arm when we talked, and repeatedly asked me to prom. I said no because I didn't have feelings for him and my parents wouldn't let me date yet, so I was just going with friends. On the day of prom, my friends and I congregated at one of our houses, and he was part of the group. Even though I'd told him I wasn't going with him, he'd brought me a corsage, introduced me to his mother as his girlfriend, and hung around me the entire night. When I stood up to dance with the rest of my single friends, he would always come and dance next to me; everyone thought I was his date. When people asked him if we came to prom together, he'd tell them yes, because technically we'd ridden there in the same limo.

  A REAL T-BONER

  My parents pressured me into a date with a friend of a friend's son, who went by the nickname T-Bone. I assured my parents that though I was living in the south, it didn't mean I would date someone named T-Bone, but they told me I was being a snob and so, to prove them wrong, I went. He suggested meeting at a chain steakhouse called T-Bones; I could not make this up. When we met for dinner,

  I was surprised to find that he was missing two front teeth. He told me about the double-wide trailer he lived in on his father's property and proudly told me about his pet goat. I'm an animal lover, so this was kind of redeeming, until he told me that he kind of hated the goat but kept it around so he wouldn't have to mow the lawn. We made small talk about my job as a Latin teacher. He responded by telling me he was fascinated because he's always wanted to visit Latin America. Sigh.

  SHOW-STOPPING PERFORMANCE

  He seemed great and asked me out to dinner and an improv comedy show. An hour before he was supposed to pick me up, he texted that he wasn't hungry and we should just meet at the show. I sort of frowned at that, but I refused to let the little setback dampen my mood. When he picked me up
and we headed over to the theater, he was a lot quieter than usual. He sat stiffly in his seat, didn't move, and eventually started clutching his stomach. I pretended not to notice, but what I couldn't ignore was the vomit that started spurting everywhere—he leaped out of his chair, clapped a hand over his mouth, and bolted for the door in the middle of the show. I felt awful about it and followed him outside. When he stopped barfing, I asked if he was okay. He said, "That's why I didn't want to go to dinner," and went to wash up in the bathroom. When he came out,