27 Worst Dates Ever

The bad, the ugly, and the uglier a collection of the worst date stories ever.
nerdy guy
The bad, the ugly, and the uglier — a collection of the worst date stories ever.
nerdy guy
1 of 27
Dating Disasters
After a bad breakup, I let my mom set me up with the son of one of her friends. I knew nothing about him other than his name and the fact that he was 16 years my senior. I like older men, so I agreed. It ended up being the shortest dinner date in history — a total of 22 minutes, mostly consisting of him making outdated pop culture references in an attempt to relate to me. Every time I tried to steer the conversation towards his interests or some kind of mutual ground, he would come out with questions like "So what's your favorite show on MTV?" and "So how about that Tom Cruise and Nicole Kidman?" (You're a little behind, buddy). I was bored to tears and couldn't wait to get out of there. —Dee, NJ
2 of 27
Dating Disasters
I once went on a date with a guy I met online. He looked normal enough, and I agreed to go on a date with him. We met for drinks, and things were really going well. Handsome, charming, seemingly normal, so I agreed to go on another date with him. We head to a really nice steakhouse, and after appetizers and his third martini, he starts to speak baby talk to me, as in "Would you wike a wittle kissy-wissy?" Our steaks arrive and he reached across the table to cut my meat for me! I'm completely freaked out, decide I'm going to the bathroom, and he asks if I need help wiping. (I wish I was making this up.) I make it to the ladies' room, where my waitress walks in after me as I'm planning my escape route, and she says, "Um, I was just listening in on your date. Your guy has put a pacifier on your plate. Do you need to get out the back?" She winds up sneaking me through the kitchen, and I slipped her a $20 tip. —Kristin, NY
woman shocked at laptop
Muharrem Oner/iStock
3 of 27
Dating Disasters
Though we had really hit it off on the phone, when we met in person, my blind date looked nothing like he said he did and spent our entire date talking about how unattractive he is and how women constantly reject him, asking me if I thought he was ugly. I cut the date short, declined a second date, and thought I was in the clear when I didn't hear from him for a couple of days. Then, I got an e-mail from him: not a single word, just a photo of his penis. —Diana, NJ
woman annoyed at date
Image Source Photography/Veer.com
4 of 27
Dating Disasters
My date told me he wanted to take me to a restaurant out in a ritzy town that was pretty far from where I live. Less than a minute after I get in the dude's car, he's like, "I forgot that you lived so far out. Do you mind if we don't go to the place I suggested?" I said no, not at all. Then he says, "Good, 'cause I don't really feel like driving way out there and then bringing your ass all the way back home. I mean this is just a first date." I decided to give him the benefit of the doubt, and we went to one of my favorite restaurants. We eat and he orders two drinks. He does not pay for my meal. Then once I pay for my half and leave my tip, he puts down $20 and asks me if i have any more small bills because he doesn't want to break his other $20. I told him to ask the waitress to change his damn $20. We leave the restaurant, and he says, "This always happens to me when I drink rum. It makes me have to pee." We keep walking, and then I realize I'm walking by myself because he stopped to pee in the alley, right in front of me. —Erin, DC
bottle of pills
Hugo Chang/iStock
5 of 27
Dating Disasters
A guy took me to the Tompkins Square Park dog parade on a date, followed by brunch, where he told me about how he can't have orgasms because he's on Prozac. And oh, could I cover brunch, because he makes like zero dollars. —Julieanne, NY
heart key on a keyboard
Maya Kovacheva/iStock
6 of 27
Dating Disasters
It was my first date with a guy I met on an online personals site. We had a couple quick conversations online, but he said he wasn't a great writer so we had agreed to meet for coffee. As I sat, I imagined the really cute guy and unbelievable credentials, and was extremely excited to meet him. Finally a guy sat down and introduced himself as my date, but instead of the 25-year-old I was expecting and was pictured on his profile, he was overweight, balding, and at least 50. He ended up talking to me for at least a half hour about how he was a 25-year-old in a 50-year-old's body, and that the picture was from his youth. Needless to say, I didn't call for a second date. —Samantha, AZ
Jeffrey Westbrook/Studio D
7 of 27
Dating Disasters
I was 25 and working at a restaurant in a busy mall. There was a guy who worked at the art store next door to us who asked me out. We went to a nice restaurant and had just ordered when he leaned over the table and said, "I shave my balls." I excused myself, went through the kitchen and straight out the back door to a bar to use the phone to call my friend to pick me up. —Viki, WV
police car
Maciej Korzekwa/iStock
8 of 27
Dating Disasters
On my fourth date with a guy my mom set me up with, we were playing pool and enjoying a couple of beers when a girl came up to our table, introduced herself, and then threw her beer on my date. The girl left, and about 30 minutes later, the police showed up and arrested him. They then took me in for questioning and asked me how long I've known him, where I was on this day, and so on. I then found out my date had set his roommate on fire and thrown him down a flight of stairs. Now he's in prison, and I never accepted another blind date invitation again. —Kim, GA
woman being ignored by two men
Joseph C Justice Jr/iStock
9 of 27
Dating Disasters
The worst date I ever went on was with a guy I'd known in high school. Jack was the captain of the basketball team, an A+ student, and all-around good guy whom I'd only admired from afar during my senior year. I saw him at a party 10 years later, and we ended up having a conversation. By the end of the evening, we had dinner plans for a few nights later. He picked me up right on time and had the reservations made — all good signs, right? WRONG! The gregarious guy from the party apparently had left on a permanent vacation, and I was suddenly sitting next to Mr. Silent. Then, a couple Jack knew sat behind us, and he proceeded to turn completely around and have a conversation with them. He didn't even acknowledge my presence! It was horrifying. My saving grace was a friend of mine who happened to be waitressing that night. She saved me with an "emergency" phone call. Jack didn't even offer to drive me home when I announced I had to leave; he said "okay" and kept on talking! The best part of the story? He actually called me the next day and asked if I wanted to go out again! —Bethany, MA
20 dollar bill
Emrah Turudu
10 of 27
20 Dollar Bill
A Better Way to Spend $20
man whispering secret to woman
11 of 27
Dating Disasters
Last weekend marked yet another futile effort at getting a date. It all took place at a brunch birthday party for my friend. After finishing brunch, we were having a few drinks. I sauntered over to a table where a really cute girl named Jessica was talking to her roommate and three of my buddies. I thought Jessica was cute as soon as I walked in. This does not explain why I started talking about a porn I had written in my head with my friend Luke. Luke and I are not a good combo. We egg each other on, and horrible thoughts that lurk in the depths of our minds somehow make it out for discussion. With Luke at the table, what should have been a done and done sentence about my porn turned into a full-scale discussion. We moved to another bar, and I decided that my porn discussion had not damaged my chances. What transpired next may have done the trick. At the bar, there were a bunch of beer-pong tables. As Jason and I took the table against Jessica and her roommate, we declared University of Delaware dominion and started sinking shots. With each shot, I peppered them with banter, infuriating them. By the time Jason and I had defeated them, a beating similar to Vikings raiding and pillaging a peaceful seaside town, Jessica was telling me to get away from her. She also smacked me. —Rich Santos, NY
couple kissing in a car
Patrick Heneise/iStock
12 of 27
Dating Disasters
After a late dinner, my date and I decided to take advantage of our remote spot in the parking lot and started getting hot and heavy in the car. Ten minutes later, I was putting my clothes back on while being escorted out of the car by a police officer. My date was behind the wheel and had to convince the cop that he was sober while I had to swear up and down that I was undressing of my own volition before he let us go. —DV, NJ
woman sitting on the couch
Mei Tao
13 of 27
Dating Disasters
I was out with a new man I'd met. We had a great time, and he suggested we go back to his house and watch a flick. So we were talking and watching a movie and were having a glass of wine when he mentioned something about going up to get a cigarette. He slipped away and I didn't think anything of it, until 30 minutes later when I realized I was still sitting on the couch in this stranger's home. Alone. To keep from bothering him, if he was talking to some friends or something, I texted him to ask him where he went. He texted me back 10 minutes later to tell me he was in bed. He left me, the first time in his home, alone. On the couch. For 40 minutes. And went to bed. I was so irked I just got up, put the wine away, and walked out quietly. Needless to say, I didn't call him again. —Ashley, CA
drunk couple fighting
14 of 27
Dating Disasters
My friend Carrie met a guy named Robert on Match.com, and the two went out on what started out as a normal, delightful date. Robert stretched the truth slightly, telling Carrie he lived on the Upper East Side. Turns out he lived in Harlem (at least another 1/2 hour from her place in New Jersey), so there was no way she was going to do the late night trip back to Hoboken. When they got to Robert's apartment, they were having some wine and discussing regular topics while sitting on the couch, when suddenly Robert flipped out about his career. He got up, paced about the room, and muttered to himself about his career failures. Carrie, creeped out by his sudden shift in behavior, decided to turn in for the night, went to bed, and pretended to sleep. Once Robert thought Carrie was asleep, he downed a handle of Jack Daniels, while his ranting grew more and more disturbing. Carrie tried to calm him down and urged him to come to bed and go to sleep, which he finally agreed to do. But he got up again and went back to his Jack Daniels, downing shots of it this time. After things had finally quieted down, she noticed a strange sound coming from the corner of the bedroom. She got up and saw Robert in the corner of the room where all of her stuff was sitting on the floor, peeing on it. Finally, Carrie made her way home to Hoboken at 2 a.m., clutching her urine-stained belongings. —Rich Santos, NY
empty wallet
Radu Razvan
15 of 27
We’ve all been there. You join friends for dinner at a pricey restaurant. They order steaks while you stick with the cheaper salad, then cringe when you all split the bill. If you can’t afford the restaurant or vacation with the girls, then say so. They won’t care. And you’ll save yourself the painful position of maxing out your credit cards.
dog in car window
16 of 27
Dating Disasters
When my date picked me up, he was with his friend, and my sister told me that his friend was married to her archenemy. Great, I was going on a double date with a girl who hated my sister. When I got to the car, I saw a dog inside — it belonged to the husband of my sister's archenemy. After we were on the road for a few minutes, the dog climbed into the back seat where I was — yes, I was in the back seat — and threw up. I rode the rest of the way to his friend's house right beside dog vomit. The weirdest part of the date was that my date brought his camera and took pictures of the two of us like we were already a couple. I never spoke to him again. —Sharon, NC
man unbuckling belt
Andrea Gingerich/istock
17 of 27
Dating Disasters
I worked at a gym and was introduced to one of the trainers at a different location. We decided to meet up for a date after work. The whole time we were eating all he kept talking about was his "special guy friend." We then walked around the outdoor boardwalk and headed back to my car. He told me he had some great CDs in his car, so I climbed in and we started listening to music. Then, he asks me if I want to see a trick. I say okay — and he pulls out his penis and begins to flex it and make it wiggle. We never spoke again. —Audrey, TN
18 of 27
Dating Disasters
My blind date had been racking up major points throwing in French throughout the night (I don't speak it). We hit it off, but I declined when he asked me to come home with him at the end of the night. He said something in French in response but wouldn't translate. It wasn't until after our second date that I found out the translation of the word — turns out, he had called me a whore! —DV, NJ
woman taking off top with man in the background
Max Power/Corbis/Veer
19 of 27
What He's Thinking
Confidence is key in the bedroom. I know if a girl seems unsure of herself in bed, it gets distracting and starts to feel awkward. The best thing to do is to act like you have some experience, and not question anything. I think back to the advice my dad once gave my sisters and me when he snuck us onto the "premium members only" tennis courts at this fancy resort at the beach. While we played, security goons watched closely, and my dad could tell that we were nervous: "Just act like you are supposed to be here, and they won't ask any questions." Sure enough, it worked.
Michal Rozanski/iStock
20 of 27
Dating Disasters
On a visit to a theme park with an ex-boyfriend, we went on the Pirate Ship ride, and halfway through, he started vomiting over everyone. I'm still traumatized to this day! —Morag, NY
couple fighting
Ellen Moran/iStock
21 of 27
Dating Disasters
John seemed sweet and romantic, and I had known him for years, so when he offered to take me out to a fancy Italian restaurant, I couldn't say no. I got all dressed up in my favorite little black ensemble and waited for him. He called and asked if I could just meet him at the restaurant. Arriving outside the restaurant, he came over laughing hysterically, and he had a friend with him. I asked him what he was doing, and he said he had been to the town bar next door drinking, and "oh my god, they had boiled eggs for 25 cents" and he had eaten a ton of them. Who wants to hear the words "boiled eggs" on their first date? His friend said goodbye, and we headed into the restaurant. John, however, had no interest in actually eating dinner. He wanted immediately to head to the bar. After asking if we were actually going to eat, John told me eating was "overrated." So there I am looking around while no actual conversation is taking place, and he turns to me and says, "Hey, you know what? You f***ing disgust me." Absolutely horrified, I had no idea what to say; I just sat there stunned. "What!?" John asked a little irritated, "Lighten up, it's a line from a movie." At that moment, although I had no idea which movie he was referring to or what planet he came from, I realized, hey you know what? I'm a smart, beautiful woman, and the last thing I need is some asshole alcoholic telling me I disgust him, joking or not. —Koty, MI
man with mullet and facial hair
Pete Collins/iStock
22 of 27
Dating Disasters
He was a bartender with an unfortunate mustache. And that probably should have been my first clue. We had a one-night stand, and I didn't think much of it when he asked if he could take me on a date. I was a little surprised when he did call, and we actually made plans. We went to dinner, where he picked what I would be eating for dinner off the menu without consulting me. We then went to a movie, and he wanted to see a horror movie. I declined and suggested two other options: one comedy, one action. The man literally pitched a fit over the movie and caused a scene over it. I gave in to the petulant child he had become and watched a horror movie featuring a vivid and graphic rape scene within the first 20 minutes. After we left the movie, we drove to Wal-Mart. Why you may ask? Because Mr. Mustache needed to buy a gun rack. Yes, he took me on a date that involved buying a gun rack after two hours of on-screen rape and murder. It was delightful. And let me clarify about the mustache: it was pencil thin across the upper lip before jetting out into thick chops that ran down a 45-degree angle to his chin! —Leah, CO
couple at a bar
23 of 27
Dating Disasters
In college, I found out from a friend that this guy who I never even met thought I was attractive. (Apparently, we frequented the same parties.) I finally talked face-to-face with him about a month later, and he asked me out on a date to a coffee shop near campus. About an hour and a $2.50 pot of some weird tea later, he explained that he had a girlfriend. Well, he lied, and afterward I found out that he wasn't into me because I wasn't "Asian" enough, and thus started dating some Japanese exchange student. Who knew I didn't pass this white boy's test of Asian-ness? Had I known he had some weird Asian fetish, I would have NEVER have gone out with him. —Arianna, NY
client dinners
Jill Fromer
24 of 27
Even if your job hasn’t bestowed on you a corporate card (the holy grail of business perks) you aren’t responsible for bills related to wining and dining clients after hours. Submit the bill for reimbursement to the firm or as business expenses at tax time—but not both.
drunk guy passed out on table
Nuno Silva/iStock
25 of 27
Dating Disasters
My friend Margaret's debutante dinner was a gala event. Her on-and-off boyfriend at the time, Jake, "invited himself" to be her date, promising that he'd behave — despite his history of reckless behavior on dates. Jake's promise evaporated faster than a gasoline puddle in the sun. After dinner, Margaret went to her hotel room to change into her ballgown. In the meantime, Jake decided to "tailgate" the ceremony. He found Margaret's friends in a hotel room and proceeded to down an entire bottle of Goldschläger. Wasted, he headed back to the ballroom and accosted Margaret's grandmother. Margaret found him muttering about fishing and pried him away from her grandmother. After returning to their hotel room, he promptly got bored and left, informing Margaret that he was going to "look for drugs." He then walked up and down the halls of the hotel, asking guests in every room if they knew where he could score some Ritalin. Upon his return to the hotel room, his drug run coming up empty, he propositioned Margaret and her female cousin for a threesome. After Margaret turned down his romantic request for an incestuous threesome, he passed out drunk. —Rich Santos, NY
guy smelling his armpit
Alloy Photography/Veer.com
26 of 27
Dating Disasters
My body betrays me during intense moments on the spot, such as first dates or fancy nights out. Here is a list of the ways my body betrays me and makes me look disgusting to my date:

1. Constant nose running: It's really tough when you're at a nice restaurant where they only give you those fabric napkins. I can get away with blowing my nose on paper, but blowing a snot wad into one of those fabric napkins is pretty foul.
2. Sweat: Body odor does not usually plague me, but I fear it. If I ever smelled body odor emanating from under my clothes, I'd just shut down the date and head home. Lately, also, I've been getting puddles under my pits. When this is happening, I just sit there like I'm in a straitjacket.
3. Breath: Why do I insist on eating garlic earlier in the day before my dates? It must be some sort of self-sabotage because garlic takes about 24 hours to exit from every pore in my body and get off my breath. There are certain things out there that you can eat that don't respond to toothpaste and mouthwash, and they just leave your breath on their own time.
4. Dry skin: When I get dry skin, I look like I have fleas, and I just can't stop scratching — not a very attractive thing to do on a date.
5. Spraying it: I usually don't do this, but when I'm drunk, sometimes I spray it instead of saying it. The worst is when food particles fly out during dinner. Again, one of these things that your date should just call out and laugh at. Covering it up is just as awkward as the act of spraying! —Rich Santos, NY
frustrated woman on phone
Picturenet/Jupiter Images
27 of 27
Dating Disasters
I'm off work early, on my way to a cupcake place. A guy walking toward me flashes me a big grin, then passes by. The guy suddenly comes back and stops me. "Listen," he says, "I didn't want to regret not saying hello." He's strapping, short-haired, dark-eyed. We chat, and he asks for my number. I'm nervous about handing over my info, but he seems normal enough. So I jot down my first name and number on a scrap of paper. Heading home. There's a message on my cell phone from the guy on the street: "Call me back." I don't. The next morning, I see several missed calls from the same guy, starting at the crack of dawn. There's a more urgent tone: "I think we have a real connection!" Calls are pouring in, from two different numbers, one private. Then come the texts: "I thought you were special, but you are SELFISH and inconsiderate." In a cold sweat now, I turn off the phone. What have I done? I turn the cell back on, and a new text awaits me. "You are going to die ALONE. Bitch." Off goes the phone. The next day, more diabolical calls. I'm too embarrassed to tell anyone I gave my number to a guy on the street. The texts take a new turn: "My cock is hard. I want to lick your pussy." Payback, I guess, for being momentarily open to a stranger. —Maureen, NY
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