bad date stories contest
Everybody's had one.
Share your bad date story!
Send us your "bad date story" via email or video and the best—er, worst—story will win dinner and a show for two: dinner at Frankie's in Lenox (a perfect choice in town for a little romance!) and tickets to Shakespeare & Company's Bad Dates. Turn your bad date into a great date! Check out this page to read the stories and share your own. Rules/How to Enter »
Latest Stories
the winning story
When I graduated college, I thought I was so cool. I had a decent job, a nice apartment, a car that went from point a to point b with no problem, and was living in Boston. What I did not have was boyfriend. There was a guy just a couple of years younger than me working in the same office as the mail clerk. He seemed to be flirting with me... but i kept thinking no mixing work and pleasure. Well he was persistent and finally asked me out not once but about a dozen times before I finally agreed.
The big date night arrived, and I was dressed to the nines. He said he would pick me up and we would goto dinner, dancing and drinking. He was prompt and dressed up nicely too nice clean white jeans and disco shirt. It was late winter and mild so I wore a lovely full length off white sweater over my skimpy sheer disco dress.
We leave my apartment and he lets me into his "car". He apologizes that he borrowed it from his mom and it is cluttered. It is white AMC (but not a gremlin). We leave proper sophisticated Boston and head for Dorchester, where he promptly takes me to the Electrical Workers hall that is having a disco dance that night! It is full of South Boston's finest all drinking heavily and smoking like chimneys. There is not a drop of food in sight. I am starving and drinking on a empty stomach. I am not having fun.
Finally it is closing time and we go outside, to leave. The car seems to be stuck in the mud. It is raining and damp and chilly. Several people try to help push the car out of the mud. We are all coated in mud and soaked through but the car is still stuck. There is not a taxi or any other means of transportation available.
He says hold on a moment I have a dry set of clothes in the trunk. Then we can walk to my mother's house and call a taxi. (This is the 70's after all)He steps behind the car and comes out wearing a cassock!!!!! He had just dropped out of the seminary.
It is now 3:00 am I am drenched, muddy and barefoot (heels are way to high to walk through the streets) and walking through Dorchester with a man in a cassock!!!
We get to his house and he calls a cab. The next day he calls to tell me that he forget he had put on the emergency brake. Can we go out again?
I figured if that was our first date it could not get worse. So I went out again. We dated for a while and we bought each other little rings. He used mine to "marry" his boyfriend and invited me to the ceremony. So much for it not getting worse.I found another job and left him behind. Times have changed but the moral of the story is still the same. Do not date at work. — Cindy B.
oooh .. bad dates - I've had plenty! I internet date. I know, awful! So the worst date? Was it the one where I had a waitress drop a tray of drinks on the guy so he would leave, because he wouldn't leave when I asked him to? No. Was it the one where the guy was 45 minutes late because "his drug deal took longer than he expected". No. How about the one with the guy who spent 45 minutes telling me how much money he made, gave me business cards to give to my friends and stuck me with the check? Nope, not that one either. It was the one where I met a guy for lunch, and even though he was about 10 years older than he said, he seemed like a nice guy - it's a beautiful day, he invited me to his house on the waterfront on a nearby island. We took the ferry over, had a nice conversation. His car is parked at the ferry dock and we drive to his house. He proceeds to drink massive quantities of alcohol. I decide I want to leave. He is too drunk to drive. I ask him for a phone book to call a cab. He says no. I ask him the name of the cab company on the island, he says he doesn't know. His brother, sister in law, and neighbor are there too. They are no help. No phone book, no cab company name. I excuse myself to go to the ladies room, grab an envelope with the address on it and my cell phone and call 911 from the bathroom. The police come and get me. They want me to press kidnapping charges, the guy is yelling that he was just kidding - I just want to go home! The police dropped me off at the ferry dock. So much for nice guy! AND last time I go to a guy's home. — Ann M.
I had a great date end badly...
In college, I asked my friend to use her car to take this girl to dinner. My friend agreed but only on the condition that I pick her up from class at 9:30 because she needed her car. I said no problem. At 5pm I picked up my date from her dorm on the other side of campus, we went to shoot pool for an hour or so and then went to dinner. Dinner was over around 7, still plenty of time to get back to campus and get my friend her car. So my date and I went back to my apartment, had a couple drinks (yeah, I know) and things started to get hot and heavy. Yadda Yadda Yadda, I wake up...yes, WOKE UP, to pounding at my door along with simultaneous bell ringing. I jump up, throw some sweats on and head to the door...as I walk through my living room I glance at the microwave clock...
2:07am!
Me and my friend Cindy went almost 3 years without speaking after that incident. I was humiliated, embarrassed and ashamed...I saw the girl for another 5 months or so, but our first date was always a sore spot for me to talk about. — Goose
Sitting close to him in the warm crowded hall, I noticed a strong smell of garlic from his direction. The music soared, and so did the garlic; I longed for the intermission when I could breathe the cool mountain air.
The garlic followed into the car and into the restaurant after the concert. I couldn't bring myself to ask him about his puppets, but he did share his interest in women: "I decided to find a woman after I had a delightful relationship one evening with a young woman. She made me realize that I was physically capable."
Now I tried to change the subject, asking if perhaps he regularly ate some particular food as a dietary practice?
"No."
On the way home, I decided that spending more time breathing the air around him was out, even though he was a passionate liberal. — Miriam R.
July 14, 1984 we met a party, he is the cousin of my friend who was hosting the party. Spent the night talking and getting to know each other.
Our first date, he took me to a party and had a little to much to drink. I drove him home and then took myself home in his car. I was woken up the next day by my father asking me "Why is his car parked in our driveway?"
Second date - he takes me to see the movie "Red Dawn" (a cinematic masterpiece), after the movie his 1972 Dodge won't start and his brother has to come to pick us up.
Third date - He takes me to see his friend play in a band at some bar in New Jersey. On the way home we are following behind some of his other friends and get stopped at a DWI checkpoint. Needless to say, the friend is arrested and we spend the night in a nearby diner waiting for him to be released from jail.
This all happened three weekends in a row. On the Monday morning following the third bad date, I was on my way to see him and break it off. Halfway there I turned around as I was having second thoughts and decided to give it another try. What followed the first three dates turned out pretty well; we were married in September of 1986 and have been together ever since. — Ellen C.
After 10 months on Yahoo Personals, I met my new husband through it. We were married last September. During those 10 months I had a lot of bad dates and here is the worst . . .
He contacted me. From his profile, I could check off some of my "must-haves" and he had impressive pictures. After a week of emails, we agree to meet at Barnes & Noble for a coffee. Arriving on time, I surveyed the small café and immediately thought "oh well, another no-show" — not so lucky — I heard my name and turned to face a "Jabba the Hut" look-alike far from the "athletically built" description listed on his profile. Strike One.
At the counter, I ordered my usual and when the barista asked Jabba for his order, he said "I'm OK" and walked away leaving me to pay for the coffee. In retrospect, I should have picked up my coffee and continued walking out the door but I stayed. Strike Two.
His conversation dwelled too much on personal information for my comfort level, so I switched it to vacations. Jabba talked about a recent Las Vegas trip.
ME: I like Las Vegas - what shows did you see?
JABBA: They were all booked up.
ME: Oh - how well did you do on the tables?
JABBA: They didn't interest me but I spent $5.00 on the 5 cent slots and lost it all!
Strike Three and I was out of there! — Kathy W.
Worst date, huh? I, like most folks, have to choose among more than one. But the worst has to be when I was youngest . . . and most vulnerable. I longed for Susan Lebe, from my generation "five feet of heaven in a pony tail". We were sophomores in high school. I finally got the courage to ask her out and she agreed, if I got a date for her friend, Ilene. So I did.
Although I was kind of broke, we went to the local bowling alley and, after I bowled a 7 in the first frame, I noticed some blood trickling down my tan chino pants. I had a bloody nose. I spent the next 45 minutes trying to stop the flow and, when I left the bathroom, the three others had finished the game. So I bowled . . . a strike. And then another strike and then another . . . seven strikes in a row. The manager of the Alley came over and said: "If you finish the last two frames with all strikes, you will bowl a 277 and I will give you a trophy".
My luck had changed. After that, I got so nervous I never bowled another strike. In fact, I would have been happy with a seven in the last two frames. If I would have gotten a spare in the tenth frame I would have broken 200 for the first time in my life. Not to be. A happy ending on the date was also not to be. Susan wanted to go directly home. I wanted to walk but she made me pay for a cab and, of course, the next Monday everyone in school knew about my bloody nose. A bad date? Yeah . . . I guess. — Gerald T.
I was on a first date with a man I had recently met. We agreed to go to a restaurant in one car — mine. That was my first mistake.
After a long search for parking, I saw a spot and grabbed it. My parallel parking skills are basically non-existent. After my fifth try, I hobbled into the space. I was embarrassed, my date was silent and we were late. He got out onto the sidewalk. I fumbled around trying to find my pocketbook and my dignity (one of which was irretrievably lost).
Finally, I'm standing in the street with the car door open. I see a car approaching quite fast. My brain, already strained, goes into overload. I thought "quick, close the door" and "quick, get in the car so you don't get hit". Unfortunately, these thoughts got twisted in the synaptic space between my ears. From where my date was standing, all he saw was me putting my head into the car and slamming the door on it. Meanwhile, the car had already passed me, and I never was in any danger, so my date really didn't see my motivation for slamming a car door on my head.
My date never flinched while I daintily patted my bleeding cheek with a napkin all through dinner. Neither of us ever mentioned a word about this incident that night or the whole time we dated. Our first date was marred by self-inflicted wounds, but we didn't even share a laugh about it. We just weren't meant to be. Whatever problems my husband and I occasionally have, laughing at (oops, I mean "with") each other is not one of them! — Debbie D.
Okay...I joined a telephone dating site. Most of the time, I've enjoyed the energy of someone's voice in their voicemail...
Her name was Anne. We talked for nearly two weeks. Pleasant, funny, even inquisitive and open woman...on the phone. We even exchanged pictures. Finally, we set a date to meet. I got to the bar/restaurant about ten minutes early, so I sat down and waited. Reading the newspaper. At last she walks in. I stood up and said "Hi...Anne?" Extended my hand. She took it...looked into my eyes. Her hand slowly morphed into the feel and shape of a squid... "You're...Ron?" Not good.
We sat. The waiter came by. "Hi -- may I start you with a drink?"
She looked around. Looked at me once more and said "...I - I just can't do this." And she walked out.
Waiter: "First date?" Me: "Yeah." Waiter: "Tough. Lemme buy this one..." — Ronald K.
My only online dating experience was lovely until the not-so-gentlemanly gentleman started talking about how his brother made up his online profile to be more attractive to women. Methought this so-called "very wealthy", "uber intelligent", and "hilariously funny" man was protesting too much when he said he would never ever ever ever do such a thing. Then he started having wandering hands. His uninvited advances and undodgable kissing led to me giggling uncomfortably trying to back away from his advances. It was an awkward trap to find myself in and needless to say, both he and I went home disappointed. I cancelled eharmony the next day. — J.W.




