Awful First Dates

by Sarah Wexler

  DEJA VU

  At my favorite bar, I kept catching this guy looking at me. Finally one night he introduced himself. Then he said, "I'm not interested in playing games. I just want to get to know a pretty girl—is that so wrong?" He came across as super sweet and earnest, if a little tipsy—he said drinking helped with his shyness. It was super flattering, because he really seemed excited about going out with me. But then a week went by, and he never called. I figured we'd just catch each other at the bar. And we did. He hobbled over, blitzed out of his mind, and reintroduced himself with the same damn speech.

  RED RED WINE, MAKE ME FEEL SO FINE

  I'd agreed to meet my date for an early drink at a wine bar, but when he got there it was clear that he'd already hit up a few happy hours on his own. He stumbled past me twice before he recognized me, teetered on his bar stool, and then ordered some pasta to help him sober up. I was impressed that he managed not to spill too much marinara on himself, but not enough to ever call him again.

  Awful First Dates: Hollywood Dispatch

  "I've been on a lot more bad first dates than good ones—there's been so many. For one, my mother set me up, which should have been a red flag. He and I didn't talk for the majority of the date—we just sat there in awkward silence. I ate as quickly as I could to speed up getting out of there."

  —Lauren Conrad

  Chapter 3

  MR. SEXUAL SUPER-FREAK

  After a great first date, it's perfectly welcome for a guy to go in for a good-night kiss...but it's never okay for him to go for the good-night leg hump. Maybe he's overly aggressive, or maybe he's just clueless, but either way, there are few things that have you reaching for Mace faster than a guy who gets too grabby too quickly. There are a surprising number of stories, too, of men who know there's zero chemistry and try to take you home regardless. It may seem ridiculous for them to try to score when a date is going so poorly, but it's actually a totally logical Hail Mary play: the guy has nothing else to lose. Since you already don't like him, maybe if he comes on strong you'll offer him some pity-makeout, and worst comes to worst, you'll just leave, which he was planning on happening anyway. Still, the audacity is impressive (and gross).

  Or maybe you were into him and sending him the green light, but his moves just didn't do it for you. After all, to one woman, a man who baby-talks might be superhot sexual kryptonite; to another, it's "Oh my God, did he just ask for a 'widdle kissy-wissy'?" And if a move worked for a guy once, he's likely to keep trying it on every woman he takes out...which means the one woman who encouraged baby-talk—or eyeball-licking, or a sex swing—may be the reason your first date is trying it out on you. But there are also stories of moves that are so hideously bad (coming in for a first kiss with your mouth full of deviled eggs? Really, dude?) that we can't believe they worked on anyone, ever.

  Then there are the cases of showing his kinkiness too soon. In the context of a happy, healthy relationship, full of trust and commitment, the average woman would probably be into, or at least willing to try, experimenting with some nonvanilla sex moves. But there may be no bigger turnoff than a guy trying to masturbate in front of you, drink your pee, or handcuff you to his van before you even know his middle name. But assuming you didn't meet by responding to a Craigslist fetish posting, it can make you wonder, if this is his first date move, how much further freakiness lies ahead? We all have our freak flags—but it wouldn't hurt these guys to fly theirs at halfmast for a few more dates.

  SOLO ACT

  We immediately hit it off—he was funny, intelligent, and fairly cute. After dinner, we began kissing in his living room. When he tried to take it further, I made it clear that I wasn't ready. In response, he immediately unzipped his pants, whipped it out, and began furiously masturbating in front of me.

  EAT ME

  I met a guy in Australia who was a good-looking surfer type. We went out for dinner, and over appetizers, he leaned across the table and reached toward my face. I thought he was going to stroke it (which would have been too intense anyway), but instead he pulled some sleep out of the corner of my eye, licked his finger, and said, "I can't wait to consume you."

  AND NOW, FOR DESSERT

  I went out with a guy for dinner, and we were having a pleasant chat about very general, superficial topics. About thirty minutes in, he paused, took a sip of wine, and then said, "So, can we go have sex now?" I looked at him, put on my coat, and left.

  THE JELLY MAN

  After hitting it off over dinner and drinks, we went back to his place and started some innocent kissing on the couch. After a few minutes, he got up and said he had to go to the restroom. When he came out and sat back down on the couch, I saw he'd brought with him a tube of KY.

  THE SUBWAY HUMPER

  After a great date, we decided to get on the subway home together, since we live in the same direction. I was even kind of excited when he kissed me in the middle of the crowded train. But then he grabbed my ass, jammed his hand into my back pocket, and gyrated awkwardly against my knee. He stuck his tongue in my ear, moaned loudly, and said, "Oh baby. You've got me all fired up." Ew.

  AMERICAN GIGOLO

  I found out at the end of the date that he was a prostitute.

  WORTH A TRY

  I met a cute guy at a convention, and we agreed to meet up the next night, since there was supposed to be a big party. But when I texted him to make plans, he said he wanted to hang out, but wasn't sure we should go to that party.

  I asked what he wanted to do instead, and he responded: "Well, there's a party in my pants."

  BUT IS HE A MAC OR A PC?

  After a nice dinner and some drinks, I mentioned to him that I was having problems with my computer. My date, who was a computer science major, told me he could fix it, so I invited him back to my apartment. He seemed like a great guy and I was interested, although I'm not a hookup- on-the-first-date kinda gal.

  I left him in the living room to get us some coffee. A couple of minutes later, I heard my roommate scream. She had walked in and found him standing in the middle of the room, completely naked. He said he'd heard that this move works one-third of the time and figured it was worth a try. I asked him to please leave. Instead, he sat down (still naked!) in my desk chair and continued to work on the computer. He didn't leave until I called the police, who arrived and asked him to put on some pants before they escorted him out.

  GETTING HANDSY

  He was super boring to talk to, but it was a harmless enough evening. But when he was driving me back to my place, he offered up that he had a hand fetish and proceeded to rub my hand in a creepy manner all the way home. Then, when we got to my door, instead of kissing me on the mouth, he reached for my hand and kissed it, which was kind of weird but also polite...until he started tonguing between my fingers and I had to yank it away from him and go inside.

  DINNER 'N' HUMP

  After buying me a Subway sandwich for dinner and then saying, "Don't say I never bought you anything," he told me he had to run an errand to his grandparents' house, where he tried to get me to have sex with him on the washing machine in their basement.

  HE'S A HOOVER

  After a wonderful date, he walked me to my door—very gentlemanly—and asked for a goodnight kiss. After I gave him the green light, I felt this crazy pressure on my lips, like he was trying to suck them into his mouth, so I pulled away. First kisses are always awkward...so I gave it another shot. Again, he started sucking on my lips and after about thirty seconds, the pain became unbearable, so I said good night. The next day, my mouth was covered in deep purple hickies that hurt too much to try to cover with lipstick.

  THE VAN MAN

  I'd been talking to a man online for a couple months and agreed to have dinner with him. Turns out, instead of being in his early thirties as he'd claimed, he was clearly closer to fifty. We had strained conversation over dinner, mainly talking about how he didn't want to live with his mother anymore. As we walked out, he told me he wanted to show me hi
s new wheels: a shiny, black conversion van, aka a kidnapper-mobile. He then asked if I wanted to go for a ride and opened the side door. Inside was a sex swing and handcuffs attached to the ceiling! I ran back inside the restaurant and had a waiter walk me to my car.

  OH SNAP!

  We went out bowling, and we were having a good time. For our second game, we decided to make up funny names for each other in the computer. While I was sitting in the chair typing, he came up behind me and, over my shirt, started fumbling around the middle of my back. I started flailing around and yelping—I thought there must have been a bug or something on my back he was trying to get off me. He said there wasn't and he stopped, but a few minutes later I felt him grabbing at my back again—I asked him what the hell he was doing, and he proudly admitted he was trying to show me his skills at unhooking a bra!

  IF THAT'S WHAT YOU'RE INTO

  I'd been warned before going to see the movie Irreversible that it included some graphic sex scenes, but my date and I joked that we could handle it. Turns out, I couldn't: it was a horribly depressing story that ends with a crazy-intense, nearly ten-minute long street-rape scene. It was so gnarly that people were sobbing and walking out of the theater; I thought I was going to faint. But apparently the scene had the opposite effect on my date, because the moment we got out of the theater, he was all over me.

  TOUCHY-FEELY

  I knew a guy who told all our friends that he really liked me, but I didn't find him attractive at all. He kept asking me out and I always made excuses; one time, to be nice, I finally agreed to go to the movies with him. At one point during the film, he started stroking my knee; I moved it away.

  I guess he realized I had a hole in the knee of my jeans, because a few minutes later, I thought there was a worm in my pants—i t was actually my date, who had shoved his fingers inside the hole and was basically fingering my leg.

  THE OCTOPUS

  He picks me up and says we're going to his friend's bar. When we get there, it's in the middle of nowhere in a shipping area for freight trucks, completely surrounded by giant deserted warehouses. We go into the bar, and we're the only people there besides his friend, the bartender. My date does shots all night and starts eating those nasty pickled eggs and sausages out of the jar behind the bar. I ask him to take me home, and he grabs me and starts open- mouth kissing my face, covering it with pickled-egg and sausage slobber as he grabs my breasts and butt and chants, "Spend the night! Spend the night!"

  THE NO-CUDDLE ZONE

  He was a dark, handsome grad student, and we bonded quickly over our mutual appreciation of sci-fi and craft beer. So I didn't regret going home with him.until I woke up in the middle of the night and he'd disappeared from his own apartment. I called his cell phone in a panic, and he explained, "I don't like to cuddle, so I'm staying at my office overnight. You can let yourself out in the morning."

  IN A PINCH

  We went back to his house and started kissing. Then we were just lying in bed enjoying pillow talk when he started randomly pinching the skin of my elbow and twisting it—hard. I asked what he was doing and he said he had always done that to whomever he shared his bed with, and then gave the example, "You know, like my mom and my sisters."

  THE NAKED TRUTH

  We hit it off, so I said I'd watch a movie at his apartment. A few minutes into it, I realized I was not interested in him and just wanted to go home. After his numerous attempts to try to kiss me (and me telling him it wasn't going to happen), I asked if he could take me home. He said he was too drunk to drive and that I should just spend the night. I may have considered sleeping on a couch, but his apartment was a studio, so that wasn't an option. He informed me that he sleeps naked; then he stripped down and hopped into bed.

  I walked out and called a cab.

  THIRSTY THURSDAY

  I had dinner and great conversation with a man I met online. In front of my apartment, I thanked him again for treating me to dinner, and he asked if he could kiss me good night.

  I said yes and we had a hot first kiss. Then he paused to ask if I would be willing to urinate in a glass so he could drink it.

  I guess I'll have to think about that—from the other side of my locked apartment door!

  SMOOTH SEXTER

  He picked me up to go to the movies and proceeded to chain-smoke cigarettes and spit out the window. Then he spent the whole movie trying to kiss me and cuddle (I managed to avoid all of his advances). After the movie, he asked me to dinner (I said no) then asked me out for the following night (I also said no). Finally, I got him to drop me off at my apartment. A few minutes later I got a couple calls from him that I ignored. This was followed by a text saying "SEX?"

  MR. SANDMAN

  After a fun date, we started making out. I was really into it and started kissing his stomach...and then I looked up and realized he had fallen asleep.

  MODESTY LOST

  I started talking with him online, and when we met in person, I realized he looked a little familiar, so I asked if he recognized me too. Yes, he informed me—I had dated his roommate. As if that wasn't awkward enough, my date then told me that though the roommate had never formally even introduced us, my date had already seen me naked. He then said that my ex, unbeknownst to me, had a habit of leaving his door wide open after I'd gone to bed, not caring that both of his roommates would see me sleeping naked.

  A STRAIGHT SHOOTER

  I went on a first date with a cop who I'd met in a bar. We went out to dinner, and although he wasn't in uniform, he was still wearing his gun. I told myself it was no big deal; he was nice and funny, and I figured maybe he was required to wear it at all times for work or something. As he started having more drinks, he told me that actually, he specifically strapped the gun on for our date. He also told me that he wasn't supposed to be wearing his gun at all while he was drinking, but he just liked it. As he got progressively drunker, he kept asking me if I wanted to touch his gun. I politely declined, but he was insistent. Eventually, he grabbed my hand, put it on his gun, and held it there, purring, "Mmm…how do you like it?"

  IT'S IN HIS KISS

  We went out for coffee, and he insisted we stay and order food. I took my first bite, a huge mouthful of bruschetta; that's when he chose to lean over and give me a big open- mouth kiss. I said something like "'BLLLERRRRCHHHHH!"' and pushed him away. We finished up and he walked me to the train station. He goes, "Let's continue what we started earlier." Totally confused, I said, "What?" and as I had my mouth open, he came at my face again, tongue out.

  WITH FRIENDS LIKE THESE

  My ex dumped me and I was heartbroken. A few weeks later, when he was out of town, I went out with his group of friends, including the mutual friend who originally introduced us. The guy was being very complimentary all evening and I was starting to remember what it was like to flirt. We kissed at the end of the night and I thought maybe I'd been dating the wrong friend all along. Then he tried to push my head down and said, "Oh come on, just go down on me...[ex's name] says you're good!"

  THE RUNAWAY

  I met up with this guy at a bar, where we were having a great talk. We ran into a couple I'm friends with, so they came and sat with us for a while. Suddenly my date announced he had to go buy cigarettes. Instead of going to the grocery store across the street from the bar, out the big front window we could see him cross the parking lot in the other direction, get in his car, and drive away. A few minutes later I received a text message from him asking me where I was. I answered, "Uh, still sitting in the bar where you just ditched me." He then texted back, "I'll pick you up and we can go have sex." Needless to say, I didn't respond and my friends laughed about it all night.

  MASTER OF HER DOMAIN

  We went back to my apartment and started making out. We were still fully clothed when he suddenly asked me if I would masturbate in front of him.

  Awful First Dates: Hollywood Dispatch

  "I was out walking around with a woman on our first date, and she ran int
o two of her friends. While she was turned around to talk to them, a bird shit on me. I have a horrible gag reflex, so I knew that if I didn't get away from it I would vomit.