Saturday 24th February 2018
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Valentine’s day special: Tales of very bad dates

broken heart

I have been working on the chapter of my book in which I discuss dating, and having to face all of my romantic misadventures in one place has put me in a rather cynical state of mind vis a vis love.  The truth is, I’ve only had a handful of truly bad dates (although, somehow, many bad boyfriends) and they were bad in pretty boilerplate ways—men who wouldn’t stop talking about their ex-wives, or stop talking, period.  I realize this might sound rather bush league by some standards, so please, bring me your absolute worst.

Posted on February 14th, 2018 86 Comments

86 Responses

  1. Trina says:

    I was on a first date with a guy I had been set up with by friends. He was handsome. I was a single mom of a toddler and was insecure and got the feeling I was out of his league (and in the wrong direction). At dinner, we somehow got on the topic of dentistry, and I said, “I think I have a million cavities.”
    He said, “Yeah, I can see that.”
    I didn’t talk much the rest of the night.
    That story has helped a lot of my friends laugh at their worst dates.




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  2. CC says:

    Set up by my close friend from school with his colleague/ client, who lived 10000 miles away in Australia. What could possibly go wrong? (What could possibly go right?) 5 months of get-to-know-you via email. Sweet notes. Beware great writers – we were both adept at writing. Then, Date 1 in NYC: drinks and dinner, in which his former US colleagues sent him back to his hotel to rethink his clothing before our date. Date 2: he informs me I need to come to Australia to see what I think of it as a place to live. Date 3: I meet his NYC cousin and other friends. After he returns to Oz: We make plans to see each other, somewhere in the world, once a month for the rest of the year. 2 months after the dates, I visit Australia and can see the possibilities, through the haze of the worst jetlag ever. We shop for apartments, very cool, expensive apartments on the water. 5 days later, it is over. I send him to Qualia resort (def google it) by himself, rather than go with him and laugh about our mutual folly as he suggests. I should have done the opposite, sending him to work while I licked my wounds in Qualia. Not the bad date you’re asking for, but a fun and then super-not-fun vignette!




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  3. Trish says:

    I was 24 and was set up on a date by my boss. He asked if it would be ok to meet at Tiffany on Michigan Ave. because he had to buy his mother a birthday gift (bridge cards). I was admiring a sapphire bracelet and he encouraged me playfully to try it on, which I did. I almost threw up when I saw the price tag and took it right off. We strolled down Michigan Ave. afterwards and walked through the Gold Coast (fancy). He kept talking about wanting a one of those big houses with three kids and how he saw me as the type of person who could be part of that life. The dude hardly knew me! The worst is I accepted a second date (he kissed me goodnight at my door and was an amazing kisser, which is how he got the second date). We met at a very fancy restaurant. I left to use the ladies room and when I got back to the table there was a Tiffany box containing the expensive bracelet on my plate. I opened it and instantly felt claustrophobic and faint. I told him I was feeling a migraine coming on and that I had to go home RIGHT NOW. Our waitress must have sensed the situation because she whisked me out the door and into a taxi. BTW he did end up with three kids and one of those fancy houses. His wife looks just like me, too. I ran into them at a charity function a few years ago with my amazing husband. Creepily, she was wearing that same bracelet.




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  4. Tammy says:

    I really don’t have a truly bad date experience, just a LONG string of bad, shitty men, who treated me like dirt and stomped on my heart when I was in my 20s and early 30s.




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  5. joannawnyc says:

    The only bad date I can recall is with kind of well-known artist [name redacted]. It was at least 30 years ago in the the East Village of old. He took me to a now-closed club (it had a balcony) to see the Butthole Surfers. We sat with his good friend, a performance artist-turned-actress, in the VIP section. They offered me a tab of mescaline, which for some reason I accepted. I don’t remember the concert. What sticks out in my head is he offered to walk me home (I lived a few blocks south) and along the way he decided to grab me and kiss me, in the process stepping on my foot and banging my head into a nearby brick wall, at which point I burst into tears (it hurt!) and told him to stop and he got really angry with me. Fortunately he didn’t abandon me on Avenue A, or wherever we were, but he did stalk several feet ahead the rest of the way (and crossed streets without waiting for me) and then left me at the front door of my building without saying goodbye. And then the next time I ran into him him, asked me, hurt, why I didn’t like him anymore. PS he seems to be happily married now and lives part-time in Italy.




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  6. Nicole says:

    Oh, these are fun! I love storytelling and story reading.

    I’d like to volunteer the following nonsense.

    I grew up across the street from this kid, and he was 6 years my junior. Growing up (and away) somehow closes the gap, and with both of us back in Boston (and me at 32), he asked me out. He was leaving two months later for grad school abroad, and with nothing to lose, I said sure.

    We ended up on a day trip to Cape Cod, and during that time he refused to commit to any restaurant. As in “Where would you like to get lunch?” and he’d just say “I don’t know…” and change the subject. It was really strange, seeing as we were together all day, and at some point, you know, 10 hours later, regular people are hungry.

    At some point, I’d had it, but of course, everything had closed. CLOSED. A grocery store was open. He went in and STOLE a pint of Ben & Jerry’s and 2 plastic spoons (from one of those boxes of 100 spoons, you know?).

    There were no additional dates. Though he did later tell me 2 things that I’ve never forgotten. 1. He bought me a ring. (WHY??) and 2. He felt sex before marriage was ok but orgasms were not.

    So.




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  7. Maggie says:

    I had gone on a couple of dates with a hot guy who lived in my building, when a fellow tennant intentionally set fire to the place. We were all forced out while they did repairs, and the guy went to stay at his dad’s house out of town, where I went to visit one night. For some strange reason he lied and told me his dad was Dee Schneider of Twisted Sister (this was in the late 90’s). I have no idea why.

    His dad had a hot tub in the backyard, so we decided to go skinny dipping. I followed him outside naked, and as soon as I shut the door, he started screaming at me because it was apparently locked. So we’re standing outside a house where he technically doesn’t live, naked, in the winter, trying to figure out what to do. Luckily, we found a bathroom window that was slightly cracked, which he managed to hoist me over his head to pry open. We eventually got inside, where he was still pretty pissed at me.

    We then had sex for the first time, where I learned that not only was he terrible at it, but that he was a guy who refused to orgasm until I did. I’ve never been one to fake an orgasm, but after an hour of that shit, I was just cranky and sore, so I tried my best. He didn’t believe me, and we wound up bickering about it.

    I proceeded to date him for another month (he WAS really hot) and we had several other bad dates, including to a rave (so not my thing), where I smoked something that could NOT have just been pot and could barely stand up.

    Finally, one day he invited himself over, and by the time he arrived, I decided I just didn’t want to see him anymore. So instead of acting like a normal human being, I hid in a corner of my house crouched down eating Chinese take out while he knocked on my door, surely confused about why I wasn’t home. I then continued to sit there, watching out the window as he was calling me from the pay phone in the outside parking lot. He eventually gave up and left. Of course, he was the one ex I wound up running into on the street for years, and he never stopped making me feel like a jerk about it.




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  8. Mouse says:

    I went out with a guy I didn’t really want to go out with–I was in my 20s–and I suspect he actually didn’t really want to go out with me. Both ambivalent. We parked in a garage structure and exited through a door marked exit and went down the stairs to the ground level, where we realized we were locked in. Locked in from the upstairs too. We spent the next 15 minutes pounding and yelling, hoping that pedestrians would hear. The worst of it was that the guy didn’t laugh about it–he was mad.

    Metaphor…..




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  9. Heather says:

    These are all amazing. Like Kim, I’ve mostly just had bad boyfriends – my bad dates are pretty run of the mill (clearly crazy, on coke, 100 lbs heavier than in photo, etc.). The worst boyfriends I’ve had have started as first dates that ranged from OK to good, ironically.

    But please do let me say, on this most commercial of holidays that largely celebrates monogamous heteronormativity, how much I love this site and the community Kim has created and sustained. xoxoxo indeed to all of you.

    And I can’t WAIT to read this thread. Something tells me it’s gonna be one of the best ever.




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  10. Sharona says:

    He was fascinated by my being Jewish (I’m secular, nonpracticing).

    We live(d) in NYC.




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  11. Jennifer says:

    My all-time worst date, courtesy of the Internet, was with a graduate student from Germany doing a fellowship in New York. Besides seeming to be just a generally awkward person he told me a few appalling stories, one of which involved a friend of his who was so upset over a breakup that he “beat a bum.” He relayed this tale while laughing. Almost worst was the part of the date when he told me he’d recently discovered that he’s attracted to women who look like his mother, “even her body,” while looking directly at me. Then, as we were walking down Second Avenue toward my subway stop he told me in a very neutral and curious way, “You look mad.” Could not get away fast enough.




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  12. janine says:

    Once I went on a date with a guy who offered to take me out to dinner for my birthday and told me to pick the restaurant. I picked a moderately priced ($25 and under entrees) place I’d never been before. After we got there, sat down, and looked at the menus he declared he couldn’t afford anything on the menu (we were in our early 20s at the time), and he then suggested we go out for pizza instead, which we did. Later I found out his roommate was actually his ex-girlfriend with whom he’d only recently broken up. I wasn’t even that mad at him about any of this, I just thought, what a complete and total loser/idiot. Funny thing is we have friends in common so I still bump into him once in a while. I told our mutual friend about the bad date and he laughed and said “Oh, that’s classic”.




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  13. Mary Alice says:

    I met him at a party and he was so charming and good looking, so I was excited when he called a few days later and asked me to a concert. I was further impressed when he showed up in a fancy car and a bottle of champagne and two glasses in the center console ( I know, I know, but it was the 80’s and I was young and foolish). We drove down Pacific Coast Highway sipping champagne. Once inside the concert he bought us drinks ( I think I had a glass of wine) and suddenly things went south. He was suddenly, stunningly HAMMERED. As in, mean, loud drunk, standing and screaming at the performers, berating people sitting around us…I was mortified. Whatever pleasant buzz I’d been experiencing disappeared as if someone had poured ice water over my head. At intermission he stumbled off to the bathroom and came back to proudly informed me that he’d “hurled all over the mens room.”At this point, all I wanted to do was get home safely, so I said I wanted to go home but he was far too drunk to drive so I had to drive. He handed me the keys and proceeded to berate me and criticise my driving all the way home. When we got to my house he actually asked if he could come in and sleep it off. I told him he could sleep it off in the car or on the sidewalk, but he wasn’t setting foot in my house.
    Postscript: a few years later I met him (and his wife) at a wedding and he made a point of apologizing to me. Said he’d finally realized his alcoholism and been sober for years.




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  14. Kristin says:

    My very first date (and only date in high school) was a blind date; he went to a different school, saw me in a play and a mutual friend set us up. He came to pick me up and his car reeked of weed, and not in a fun way. He then took me to a spaghetti dinner at a Southern Baptist church to which he did not belong, where this atheist was quaking in her boots. For some reason I agreed to go to a movie with him after that. As we parked he handed me cash to get tickets so he could smoke a blunt. I hadn’t gotten into weed at that point so I was horrified, but too young and dumb to protest.

    I still made out with him in my parents’ driveway later, realizing that this was my shot for a kiss during an awkward adolescence. Desperate times…




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  15. Mimi says:

    This probably wasn’t my worst date ever, but it was the first that came to mind. Circa 1996, I was in New York for Fashion Week and a friend, (okay, actually the Married Literary Lion I had a bi-coastal affair with for 10 years,) suggested I meet an eligible guy he’d gotten to know at his tennis club. MLL wasn’t trying to get rid of me. He was a lover and a friend and quite the social networker. I had a drink with the guy, who was some kind of leveraged buyout financial hot shot, a red flag I ignored. When I got back to L.A. phone calls ensued. During one chat we spontaneously decided to spend the holidays in Aspen together. We met at the Denver airport and drove to the mountains. He played the same Celine Dion CD over and over for the whole 3-hour drive and related, in excrutiating detail, the history of his relationship with his ex. When he finally stopped talking he said, “I guess you must have your stories too” and I replied, “Yep.” He didn’t know how to ski, but was arrogant enough to think he’d learn in a day. When reality bit he spent every day in ski school, a blessing that left me free to ski with a group of his friends, who were nice and fun. He was bad in bed, pushy and rude to strangers and the type who would unsubtly check out other women while I was on his arm. The trouble with destination dates is that when they go south, you’re stuck. But what’s life without some impulsive decisions? Even dumb ones.




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  16. Helene says:

    I have 2 worst: Both guys I met at a club while out with friends on separate occasions. They seemed OK when I met them & so I gave them my number.
    1st guy I met for dinner. Prior to the date & after having agreed to go out he said he hoped I would buy a new dress just for our date. I did not, but when we met, he approved. UGH – I instantly regretted not cancelling the date. He proceeded to brag about that fact that he was a bowling champion. And didn’t I love his fabulous car? I was not impressed. When the waitress asked if we wanted desert & he told her “No, I’m having HER (me)for desert”, I wanted to vomit. I couldn’t get away fast enough! He did NOT get the desert he was hoping for…
    2nd guy looked like Brad Pitt in the dark of the club, not so much in the light of day. He was very sweet on the phone, so I accepted movie date. He picked me up & proceeded to drink a bottle of Nyquil as he drove to the movies! OMG! He said he had a cold, but I think he had a case of alcoholism! I prayed for safety the whole way there & back home again! Needless to say there was not a 2nd date.
    Looking back WHAT WAS I THINKING?? I like to think I would handle these situations differently today – older & wiser.




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  17. kb says:

    Very briefly, as was the date: I was set up with a man who told me, over dinner, that he thought cocaine was better than sex. Whether it was his way of telling me I was unattractive (?), or that he truly felt that way, it didn’t matter. At the end of the meal, I left the restaurant and took a cab home.

    Enjoying these replies….some real gems! Thanks, Kim.




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  18. Rachael says:

    About ten years ago, I went on a first date with a guy in SF I met online because his picture looked like a friend I had a crush on. When we met up, he of course looked nothing like his photo, and had a major Chicago accent, which is a huge turnoff for me (my family’s from there). We were waiting for a table at a restaurant in their back terrace, and he turned to me all of the sudden and said, “I’m about to do something that’s going to totally gross you out.” I had a brief internal dialog, freaking out until I saw him reaching for his jacket pocket, at which point I realized, oh, he’s going to smoke, which, yes, I find annoying and obnoxious, but gross? not a decade ago. And he does, in fact, pull a lighter out of his pocket. But then, he reaches into the ashtray in front of us AND PULLS SOME STRANGER’S CIGARETTE BUTT AND LIGHTS IT AND SMOKES IT, explainging that it’s too much of a trigger and he can’t help himself. In one of my prouder moments, I said to him, “you know what, you did gross me out,” and I got up and left. I have no clue if he did it as a test, or because he couldn’t stand me, and I don’t really care.




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  19. Erica says:

    Here’s a few I racked up in my mid-twenties following on from a monster break up: the Obgyno blind date guy who regaled me with stories of hysterectomies over dinner – “basically I just throw uteruses into buckets all day long”; the guy who asked me in the middle of making out if I was “cool with him being a dealer” (of drugs). Answer – no; and the real winner, the guy who literally fell asleep/passed out while giving me, ahem, oral pleasure. Let’s just say wild times were bad, lessons were learned, and ultimately, future assholes avoided.




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  20. Jocelyn says:

    I had so many, many bad dates (and frankly, garbage relationships) all through my 30s I started keeping a blog about them. Sometimes I was able to muster humor, or reflect thoughtfully, or longingly at why and how it had all gone so wrong. Hugs to all who have suffered through and who are still limping along!

    http://www.bigbookofbaddates.com/thebigbookofbaddates/2014/11/the-day-of-dead-jason.html




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  21. Katy says:

    First movie date ever. We made a terrible choice on the movie, seeing “Another Country” which was about English schoolboys and sex sex sex! I was 15 and so was frozen with embarrassment. About 10 minutes in, Sam lilfted his arm to put it over my shoulders and instead he elbowed me in the nose. The people sitting behind us burst out laughing and I wanted to die.




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  22. Jane says:

    I did a fun scavenger hunt with my cousins (a guy & a girl) and my guy cousins best friend, Rex. We were zip tied together at the wrists and had to run around the city finding things. It was really fun and we actually won (a Budweiser bar mirror). Regardless, a fun night and Rex was cute so when he asked me out, I accepted. But he didn’t actually ask me out. He asked my cousin to set it up and he did, which in hindsight should have been a red flag. I mean, I was right in front of him all night but he couldn’t work up the courage? Anyway, a few nights later he arrived at my door to take me out for a drink. The first thing out of his mouth is, “ So I’m sure your cousin told you I’m in love with you and want you to bear my children?” Um, nope. It was so awkward but off we went to a bar he made me choose. He said he never went out so wasn’t sure where to go. Did I mention he grew up there and was 6 years older than me? We sat down and he couldn’t look at me, could barely make conversation and asked me nothing about myself. I pretty much talked to him like I was talking to a toddler and it was about that exciting. Finally I told him I had an early morning and had to get home. He did not say one word to me on the way home until he walked me to my door and asked me out again! What?!? I very gently told him I just didn’t think we were compatible and he just nodded and left. Two days later the Budweiser mirror appeared on my doorstep.




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  23. sc says:

    Casual date – not a love match, but nice company – go back to guy’s aprtment for a drink – he excuses himself – and then –

    Returns the living room wearing a head to toe BLACK FISHNET BODY STOCKING – all his hairy junk stuffed in the worst places –

    “I just wanted to get more comfortable”

    We had so much as held hands yet. I was trying so hard not to laugh. I got the hell out of there as fast as I could. For the record, I’m not judgey of anyone’s kink – but you have to earn the introduction.




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    • sc says:

      Had NOT held hands I mean




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    • Heather says:

      Ha, awesome. My sweetie owns something similar that he wears when he is ACTUALLY fly fishing in cold weather (? it has some kind of insulating properties? not sure). We joke about him bringing it out for… other occasions. I sense that was NOT the case here (ie, let’s go fishing in January!).




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  24. vishy says:

    I always called it my date from hell because it was the longest date in history. I was working my way through school at a local grocer and this local businessman would come in and make a point of chatting me up. I was clueless he was interested in me until WHAM he asked me out. I was on the fence but feel generous after a pep talk from my roomie/coworker and said sure, why not. Ugh. He took me out for Mexican food…in Tulsa. Strike one. I’m from Deep South Texas where the Tex Mex is amazing. What was this “cuisine”?! Not impressive. Then we went to the movies. The absolute longest movie of the year, Dances with Wolves. FOUR HOURS!!! There was literally no escape. And then coffee afterwards. I was being SO NICE, especially as we really were not especially hitting it off. He took me home and I thought well that was that. UNTIL, my schmoozy roomie/coworker announced she had worked up a little scheme with this gentleman to surprise me with brunch the next day. Oh dear LORD. I was dragged to his apartment where he dined us and proceeded to blare and sing along with show-tunes on his massive stereo. This went on for most of the day, as he and my roomie/coworker were having a blast. Under normal circumstances, I love a good show-tune, but this day I barely survived. I was nice to myself the next time he asked me out and I kindly declined.




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  25. Emma says:

    I’ve got one! I met a guy through a dating app. We were the same age, and the conversation was pleasant. He’d done a Fulbright program in Germany and now worked for the German consulate in America. We agreed to get drinks at a bar and watch the weekly stand-up comedy show they host in the back. I took an uber pool to the date. If you’re unfamiliar with pool, it’s simply like car-pooling with strangers. Uber adds people who have destinations along your route so everyone’s fare is a little less expensive. Anyway, who happens to be in my uber pool? Yup, the guy I was meeting at the bar. It was very uncomfortable. We both said hi to each other but the driver was very talkative and didn’t seem to realize we knew each other so he just carried on chatting about his religious beliefs and asking each of us questions. Finally we get to the bar and both get out. The driver was very confused. Anyway, the date progresses and we have a couple beers. It’s a pretty good show. Afterward we sit in a booth drinking beers. At this point I begin to think he is a bit cheap because he bought one round and I bought two for us and he made no effort to pay or say he’d get another round. Suddenly he starts bringing up sex. He inserts sexual comments where they do not belong repeatedly. It’s so strange. I mentioned that I thought one particular joke was good, it was a sorta sexy joke. He said “yeah you loved that.” I ignore this and change the subject, pointing to a very odd little pocket on my sleeve that I’ve never noticed before. “huh why on earth would they put a pocket here?” I ask. He says, “maybe it’s for holding condoms,” and then he stares at me without blinking. I want to vomit and go home immediately. I feel incredibly alone. One of my favorite ice cream parlors is across the street so I ask if he wants to get ice cream. He says he doesn’t, so I say oh well I’m going to get ice cream, and he is welcome to come if he wants. He comes along and watches me eat ice cream. In between walking across the street to the ice cream parlor he ducks into a taco restaurant and gets a taco or burrito or something to go. As I sit in the ice cream parlor I see him scarfing down this burrito in the street, after finishing he comes inside and watches me eating my ice cream. After finishing the ice cream I say that I’m going to go home now. He suggests we go home together. I say that I don’t think it’s a good idea. He persists. I order an uber for myself. He says he’ll wait with me for it to come. When the uber comes he runs around and gets in the other side. I am visibly annoyed. I ask the driver if it’s okay if we can make two stops. I vaguely remember the neighborhood we picked up my date. My date does not correct my estimate of his address, he moves very close to me in the back seat to the point where I’m wedged against the door. He starts kissing me and I keep saying no and stop very quietly because I don’t want to weird out the driver. He starts groping my chest and I finally say “stop the car this is close enough” and practically push the guy out of the car. The uber driver is once again very confused!




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    • Emma says:

      Oooh I just thought of another ugly app date experience. I met this British guy who was going to a very prestigious graduate school. The conversation wasn’t stellar but he seemed handsome and smart so I agreed to meet up. I picked this cute neighborhood bar that has several hundred craft and Belgian beers. It’s called the Hopleaf, you get the picture. I am standing outside the bar and a man says my name. I say hello not recognizing who he is and then I realize it’s the man I’m meeting except he has recently gained quite A LOT of weight. I would estimate 60-80lbs. Maybe more because he was very tall and I’m not great estimating weight for men. I acted like I didn’t notice the drastic change in his physical appearance. We go in and get a table. He asks for a vodka and diet coke. Apparently this is his go-to drink, and the only thing he really drinks. I mention that they have a great beer menu and he says he doesn’t like beer. I apologize for choosing this bar, but he doesn’t seem to care or understand why I’m apologizing. The bartender says they don’t have much vodka, and my date has to settle for some brand he doesn’t like. The conversation is HORRIBLE. He mentions that he went to Exeter for undergraduate school and I say that the name is familiar and he is deeply offended and continues to tell me how difficult it is to get into that school. Then he asks me to google their acceptance rate. I tell him I believe him. He continuously tells me about his famous father and how successful his dad is. At one point I say, maybe I should go on a date with his father. He doesn’t get this joke. I ask if he likes cider because this bar has a decent selection of craft ciders. He says he does like cider but only Angry Orchard. I go order more drinks for us and wince asking the bartender if they have Angry Orchard. The bartender laughs at my facial expression. The date continues on and the guy offers to help me get a better job. He tells me to send him a resume and he’ll find me something where I’ll probably make more money than the nonprofit that I work for. I eventually make an excuse to go home. He asks if I want to hang out at his place (my god did he think it was going well?!). I say no and when I go to pay for the round of drinks I’d bought, the bartender tells me his name and when he works at the bar and says to come by if I ever want to hang out. The bartender hitting on me was actually very sweet. I was feeling like such a loser and it felt like this little nod, and someone saying “hey I see you.”




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  26. EW says:

    High school, somewhere in the 80’s…me about 16, date, guy about 2 years older, from a local prominent family, football star, a friendly fun happy guy..my parents were all gushy and excited; he took me to his grandparents for dinner, but it wasn’t a special dinner in fact I don’t think they were expecting us we just showed up but they were nice and I kind of thought it was sweet, but then we went and sat in a parking lot of a park with his friends where he proceeded to drink about a case of beer and practically passed out; I had to get his friends to help me load him into the back seat and then I drove him home, left him in the car and then I walked home! (it was smallish town, and not that far) no cell phones or uber back then. My mom asked me about the Big Date, and I just said it was fine. I think he is in local politics down there these days.




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  27. mlinky says:

    Ahhh, THE date from hell.

    I met a pretty good looking guy at an alumni function. He was a journalist and attorney, and head of the international law department at the university. He asked me out for drinks, I said yes, we set a time and planned to meet at a comfortable neighborhood bar the next evening after work.

    Right before I left, he called me and said his car had to go into the shop, and would I pick him up? Sure, no problem. We got to the bar and ordered a couple of drinks. He pays for his, and I pay for mine. Well, he did do the asking out, but no biggie. The whole time, he is talking about how great he is. Boring, but not nearly in ‘date from hell’ territory.

    He orders a second drink, and that is where things got weird.

    You ever deal with a seriously sick individual who doesn’t think right, but is smart enough to pretend to be normal? That is him.

    First, the conversation rolls to his work. He starts talking about his assistant, who he had apparently received a blow job from a few weeks before, because ‘she wanted him badly’; he was such a catch. Then he says ‘you know, I could fire her for that’ and seems to be looking for my confirmation that he is such a nice guy to have not done that.

    At this point, I am almost speechless, although I have barely gotten a word in. Then the bartender asks for us to pay for the second round and he says, ‘oops, I thought I had more money with me…will you pay?’ I handed the bartender some money, and he orders a third drink. I don’t object. I am busy planning my exit and figure it will be easier the drunker he gets.

    I was totally creeped out. It’s obvious this guy hates women. Seriously hates them, but usually has enough of a veneer to hide behind. He starts talking about various ‘conquests’ (including one that he claimed to have taken in the bathroom of the bar) and exhibits disdain for them all. I believe that I was hearing the honest thoughts of a sociopath/psychopath.

    He excused himself to go to the bathroom; I left and went home. It’s raining and I don’t care that he will have to find his own way home. I never heard from him again.

    Two ‘funny’ things later…

    About 5 years later, I was talking to a woman who I worked with, and comparing our dates from hell. She told me a strange tale of a guy who weirded her out, and it was the same guy.

    About 20 years later, I saw a news broadcast about a former university employee who was arrested after violating a restraining order and entering the library with guns. The name sounded familiar. It was him.




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  28. Achariya says:

    I dated a nice enough fella while working for CNN, a programmer. He refused to clean his bathroom while dating me, so I tended to leave in the early morning to head home and shower in my own clean apartment … Until one day I found him frantically cleaning his bathroom, because his “best friend” (a woman) was flying in to visit him from San Francisco. I really don’t know why I didn’t break up with the inconsiderate guy then and there, but it actually lasted another year. Ah, to be dumb and in my 20s.




    5
  29. AG says:

    I would say between the mid-late-90s into the 2000s I had more “date, not a date” experiences which ultimately made me just give up on dating all-together. This was before online dating, dating apps etc. What is a date not a date? You think you are on a date, it has all the hallmarks of a date, but then you start to get mixed signals and you start to question your perception, your sanity, your game, only to have a date-like gesture happen just to confuse you and then…nothing. OR you would find yourself on a date without knowing how that happened.




    7
  30. Bex says:

    I’ve never had a truly terrible date, just ones that were so boring I feared I would fall asleep sitting up. The worst was a guy whom I knew through mutual friends. He took me to a cheap taco place, and the “conversation” was excruciating.
    Me: “So did you grow up around here?”
    Him: “No.”
    [long silence as I gave him a chance to elaborate]
    Me: “Where did you grow up?”
    Him: “[Nearby town].”
    [long silence]
    Me: “How long have you lived here?”
    Him: “Ten years.”
    [long silence]

    Lather, rinse, repeat. He never did ask me any questions about myself. After about half an hour, I told him I needed to get home because I had to get up early the next day.

    The sad thing was, I found out through our mutual friends that he told his parents that we had a great time and he knew I was “the one” for him. Nice person but completely clueless.




    6
  31. Melissa says:

    No horror stories, but I just wanted to say that these stories are helping me get through my first single valentine’s day in 15 years (got divorced in October). Though I can’t say they’re giving me any confidence to start dating again!




    17
  32. Heidi says:

    The guy who told me he’d had a vasectomy on the first (and only) date just to be clear that he did not want to have kids.




    9
  33. Francine says:

    Love this post and all these great stories! I’ve been with my husband since the end of my sophomore year in college, so my dating is super limited! But here’s my “bad” date.

    It was spring after my father past away and I was living with my mom and brother in Southern CA. I was a sophomore in college, obsessed with good grades and the LA Dodgers. Trust me, I was no athlete, but LA baseball was hard to resist, especially in the spring. When the games weren’t televised, I actually followed them on the radio. I listened in the car on the long commute to school (the 405 was bad even then) or late in the evening while studying. But I was bound to miss some simulcasts, bound to miss the games. But crazy girl, I needed to know the score. Long before the 24/7 ESPN or the internet, the LA Times had a sports hotline (do they still?). No matter the day, no matter the hour, someone always answered. Most always sounded surprised when I called. It wasn’t long before I started to recognize the voices.

    His name was Jeff*. He was a young reporter, pretty fresh to the Times and typically manned the phones after 11pm. He was curious about me….why was a college girl calling about Dodger scores (they were awesome in 80’s!), did I play baseball (God, no!), what was I studying (political science…yeah, I know….career maker) and what I wanted in a guy (a baseball player of course). After a while, I called the hotline – even when I knew the score – just to talk. He was funny, sounded very cool – and better still – thought I was cool! Finally, a guy who thought my interest in sports made me a catch!

    A few weeks later, he asked me out. To a Dodger game! Honestly, could it have gotten any better?

    Sunday afternoon arrived. The doorbell rang. He was in his early twenties, dark hair still fresh from a shower. He was cute. (In my Dodger blue-clouded haze, I remember thinking that he sort of resembled a very young Davey Lopes.)

    We never described how we looked (no ‘selfies’ or Facebook pages, remember?). He was kind. He didn’t say what was clearly written on his face. He was disappointed.

    The drive from Orange County to Dodger Stadium was a long one. I remember trying to make small talk, trying to rekindle the phone chemistry that had kept us talking for two months.

    The game itself was uneventful. We didn’t talk much. It was strained. I’m sure he was praying for a rainout, or at the very least, no extra innings. The evening ended with some random thanks and pleasantries. I remember telling my mom how bad I felt that I wasn’t cute enough. I stopped calling the hotline for baseball scores and had to suck it up and wait until the morning paper hit the driveway.

    A few months later, I was with some friends in the stands of college baseball game and saw him in the bleachers taking notes. I walked over to say hello. I’d lost 30 pounds over the summer (not because of him – or any guy), lightened my hair and was wearing shorts. By then I was dating one of pitchers and I knew I looked good. To his credit, he didn’t do a double take or suddenly fall in love with my better-looking self. We talked about baseball and something about how he was now covering boat racing. He’s still a reporter for the Times, and frankly hasn’t aged all that well. I, on the other hand, am a stunner 🙂 !!




    18
  34. c.w. says:

    I haven’t actually dated since high school. I’ve only gotten married. So no bad dates, only bad marriages.

    Love reading all the postings. Such a brave, strong, funny group of women!!




    6
  35. chelene says:

    ummmm. I was the bad date.

    Yeah. Sooo, back in my mid-20s (am 47 right now), I somehow attracted the attention of a late-30s, early-40s male lawyer. Lemme back up and clarify: I worked in a bar, he was a frequent customer as his law office was directly above the bar, he and his buds came in quite a bit. On slow nights, I was “allowed” to drink with the customers. He and I drank.

    Fast forward to the holidays and his office is having a party at one of the senior level people’s lovely house, and he invited me. From the minute he picked me up, I committed a number of infractions: garlic pizza for lunch (i heart garlic, but was burping it up), over-dressed and over-makeuped, slightly drunk. Then we get to the party. The music wasn’t loud enough so I made my way over to the stereo and turned it right on up. Then smiled brightly and sat down in the midst of the wives and g-friends who were looking at me strangely. My date had semi-disappeared. So I drank. And I drank. (I didn’t eat.) Aaaand I drank some more. I puked in the bathroom, borrowed a towel and tried washing my hair. Reappeared by the food with a partially wet head and blouse and smeared mascara. Proceeded to drunk-eat my way through the table whilst the men just watched and didn’t say a thing. Still no date. Went to eat a carrot. Dropped the carrot on the floor. Squatted down to pick it up and then somehow couldn’t keep my balance despite being so close to the ground (and what I thought was a very graceful squat) and started to fall backwards. Someone hauled me up to standing (date? sympathizer?) and I said thank you and resumed eating the carrot, then thought “I’m drunk” and then started giggling. Spewed chewed carrot on food. Then farted. Then I laughed because why not. Even drunk me knew there was no going back.

    I can only surmise that someone told my date that I needed to go home because next thing I knew I was being hand-walked to his car and firmly belted in. Went to his house, had bad sex. I’d bathed in Samsara pre-date, and the smell of it woke me up at like 3 a.m., where I found his bathroom, puked again, and then went poop, which let’s be honest, poop smells bad but this smelled like someone had died. No air freshener or window to open, either. I took a shower then went and slept on his couch and woke up with a horrible hangover and probably slept it off the rest of the day once I got home and did the walk of shame to my apartment.

    He didn’t come around to the bar much after that. I moved on from the bar to a real job in my major and left the bar/partying/drunk scene behind. Yes, I’m a fully-functioning adult who (mostly) no longer embarrasses herself.

    I did see him once, though, about 2 months later, just showed up at my apartment unexpectedly with a poem and a bottle of wine. I still have the poem somewhere and I’ve since drunk the wine. Nice guy.




    19
    • Francine says:

      That’s some story! And yes, it sounds like you were a terrible date. His version is probably posted somewhere on Mantelligence or something.




      3
  36. Karen says:

    Bad Date 1: Date w/ a guy who was a friend of a friend. He showed up over an hour and a half late (this was before cell phones, so I was almost in tears thinking I’d been stood up). When he arrived to pick me up he asked if we could just go get fast food (I had been looking forward to fancy Italian dinner). We compromised at a chain restaurant (he asked me to drive) and then went for coffee where he discussed a boil he had recently had on his back, and having it lanced, IN DETAIL.

    Bad date 2: Drove to meet a guy I’d had a crush on for months at his apartment. We were driving to get drinks and meeting another couple for dinner. Turns out his car had no seatbelts and barely had seats (springs covered with torn fabric). I refused to ride in it for safety reasons so I had to drive (notice a theme here?) We went to a bar where I couldn’t drink because I’m a lightweight and was driving. Then we met my friend and HER date for dinner. Turned out the place we were dining didn’t serve alcohol. This was when I discovered my date was basically an alcoholic or at least, couldn’t function on a date without copious amounts of alcohol. Imagine your worst first date conversation X2 because it was TWO couples on a first date. Did I mention one of us was wearing leather pants? (Not me). Went back to his place after dinner for a drink. The apartment was covered with cat hair and we (he) talked about his passion for James Bond movies.




    6
  37. Alexa says:

    These are all amazing.
    I have quite a few doozies, but I’m not sure I’m ready to tell her hem. But I applaud all of you!




    2
  38. Francine says:

    BTW ladies, don’t you think this would make a FABULOUS topic for our GOACA conference? I volunteer to draft an agenda! Kim, your book will write itself.

    xxoo




    9
  39. Gables girl says:

    My mom set me up with a college mascot, which was a very big deal at the time to this Southern sorority girl. I saw his picture. Super cute sitting on a stallion in his costume. He picked me up at the front door and to my surprise he was under five feet tall. I’m 5’6 in stocking feet. No more mom set ups.




    5
  40. Laura says:

    These stories are all wonderful! Here are my contributions, both from back in the day Lavalife.

    1) A truly nice fellow who initially had pretty decent conversational skills and talked about a lot of cool bands and movies that he liked. I guess he then thought that we were comfortable enough with each other that a first date could include talking AT GREAT LENGTH about his prolapsed sphincter and “excessive mucous production.” I went out with him a second time, because I had some sense of a moral obligation, I guess, but suffice to say, the magic was gone. I’ve worked hard to repress those details for a decade, so congrats to me for recalling them.

    2) Another pretty nice fellow who invited me to watch him DJ at a bar near my place. I went to said bar and was hanging out in the DJ booth (feeling like a cool kid, obvi) when this woman walked in and started to interrogate me about who I was and what I was doing with her partner, to which the guy said, “EX! EX-PARTNER. We broke up six months ago.” The lady then said, “Yeah, but you knew we’re getting back together because we always do.” Um, yeah, my pretty fun first date didn’t just get super awkward or anything. She eventually left after they snarked at each other, and I politely made my excuses and left not longer after. We went out a second time, and one of her friends saw us walking down the street. Two minutes later, he gets a phone call from his ex, super upset that he’s out with someone who’s not her. They proceed to have a phone fight on the sidewalk, and I proceed to politely wave goodbye and, I don’t know, go watch a Bridget Jones movie or something. No third date needed.

    3) I could definitely also tell you about the time that I dated my good friend’s ex (yes, I was that person, and yes, it was a terrible decision for lots of reasons), but that’s a book on its own. I do look back at what was the most toxic two years of my life and think that I must have been drugged. That’s truly the only logical explanation for hooking up with such a total piece of garbage.

    Happy Galentine’s AND Valentine’s to you all!




    9
  41. Claude says:

    Went on an online date. The guy mentioned that he lived in the suburbs, in a four bedroom house. I asked what he used thd rooms for and he said “Snakes.” I asked for more detail, and he responded that he had three pythons. “I couldn’t expect them to share a room.”

    I saw him at Petco, years later.




    16
    • Linda E. says:

      In 1980 I was 21 and new to the bar scene. I met a cute guy who asked
      For my phone number and we made a date to go bowling. He picked me up at my parents’ house and said before we went bowling, he wanted to show me the house he had just bought. So he is showing me around when I spot a huge aquarium containing a huge snake. I told him I was afraid of snakes and he proceeded to take the cover off of the aquarium so I could pet the snake! I ran for the front door, which was locked and then went for the back door whichwas not locked. Just as I was opening the door he came up behind me and pushed it closed.

      Somehow we got out of there without getting the snake out and went to the bowling alley. Turns out he was bowling in a league and I was stuck watching the jerk bowl three games.

      When he took me home he said, “I won’t be asking you out again.

      Thank God!




      2
  42. Mamavalveeta03 says:

    I discovered why you don’t go out with the guy with the super-hot car: It probably means he is the most boring man on the face of the planet…the car isn’t just a penis substitute, it’s a personality substitute!

    My cousin set us up, and since he was a good looking Scandinavian from Minneapolis and drove an MG, which I thought was quite romantic, I said yes when he asked me out to dinner. He seemed very nervous during dinner but after, he asked me if I wanted to go for a walk by Lake Harriet and I was thinking, “Well, maybe he’s just not a conversationalist, but he’s great at makeouts.” He said he had a surprise for me, and tho I was cautious, I knew he was harmless…he was shaking, for heaven’s sake!…I said sure. The next thing I know, he’s knocking on someone’s front door…it’s got to be a celeb, right? Nope. Unless you consider former Minnesota Vikings coach Bud Grant’s NEIGHBORS celebrities! We spent an hour sitting around “Ole & Lena’s” table drinking beer, then walked down to the lake where he asked me if he could kiss me. I gave him a mercy kiss…I thought he was going to have a nervous breakdown after all of that excitement at the neighbors place. Never again!




    6
  43. Christina says:

    This last line wins it for me.




    2
  44. Cat says:

    Early twenties, I met a guy who was a few years older than me and had gone to the same university. He took me out to a fancy dinner and proceeded to tell me in great detail about his career as an investment banker. And that he lived with his parents because it was the wisest move financially while he saved for his Connecticut mansion. I was bored but naive and decided he was nice enough and perhaps just nervous.

    We went to a Cranberries concert (RIP) and because I was used to cheap lawn seats, didn’t keep track of my ticket. After leaving our seats to grab drinks, I couldn’t find my ticket for the worker granting entrance to the front area. My date proceeded to yell at me while I frantically searched my purse and pockets, and nothing. He stomped down to his seat leaving me alone. The guy working felt sorry for me, and let me find my seat after a few more awkward minutes of searching. My date acted like nothing was wrong, and told me his parents wanted me over for dinner that weekend. They were so excited he had found “the one” and that she was an alumnus. Oh and he told me that working at a non-profit was kind of a waste for someone who had graduated from a school like ours.

    I didn’t go to dinner.




    7
  45. Amy says:

    I’d started messaging with a guy and he said he’d be passing thru a nearby train stop and would I like to get a drink? I said sure! I walked up to him and said “hi, Jason?” and he goes “yes! How are you? You know, you’re a bit taller than I was expecting”. I told him that I had put my correct height on it, which is 5’11”, so there’d be no surprises. He looked a little confused then shrugged.

    We found a place to go for a drink and had a decent conversation for an hour, before things started to go downhill when I mentioned my mom was from the same area he grew up in.

    Me: My mom is from your area
    J: oh yes, you said she died from cancer
    Me: No, she had cancer but she’s in remission
    J: No, she died
    Me: No
    J: Yes, she died
    ME: NO
    J: YES!!
    Me: OMG, QUIT SAYING THAT, MY MOM DIDN’T DIE FROM CANCER!!!

    I couldn’t believe he was arguing with me about whether my mom died or not, and it was also at that point I realized he thought he was on a date with another girl. So, I wrapped things up quickly after that and turned down his suggestion to get a bottle of wine and go to my place.




    10
    • Lorange says:

      Arguing with you about the facts of your life is amazing. Familiar (because men), but still amazing.




      7
    • Heather says:

      During my internet dating days I loved it when they made it SO OBVIOUS that they couldn’t keep track of the myriad (ie probably 2 or 3) women they were chatting with. “Were you the one who…?”




      2
  46. Mimi says:

    More memories, with a theme: the surgeon who played a tape of the songs he’d composed and sung the minute we got in his car. They were terrible. And the businessman who begged me to read and critique his play. It was beyond terrible, but he didn’t want to hear constructive criticism, only praise. When I told him I didn’t think it would be a good idea for me to give it to the executive director of a theater company I knew, he pouted and said he’d rent a theater and produce it himself. It felt like these guys thought that because I was a writer I would enjoy and support their “creative” endeavors. One actually said “I feel more creative around you.” I felt like they were vampires who hoped if they bit my neck and sucked out my skills they would be transformed. Yuck.




    7
  47. Krista says:

    I thought I didn’t have a bad date story…then I remembered the time my boyfriend got us entangled with the Japanese mafia.
    I was living in very rural Japan and met an incredibly fluent cute Japanese guy in the capital city. After a few months of dating, he came out to meet my fellow English teachers.
    We went to an “all you can drink” bar (side story: we begged them to give us a “foreigner price” that would be higher, they refused, and we literally drank them out of business in three months.) and I guess he was nervous because he got completely hammered.
    We stopped at the public toilets before going home. I was waiting outside and he came running out full speed. Behind him were three guys catching up quick. Then I noticed a low sleek car also on the move. By the time I got there, he was on the ground and six henchmen (super femme with crazy plucked bleached eyebrows and creepy fingernails) surrounded him, punching and kicking at him. He was speaking in a verb tense I couldn’t really understand, totally submissive. But I got the impression he had insulted the size of someone’s dick in the toilet.
    I stood beside the guy who was clearly in charge and just started being the big dumb foreigner in my terrible Japanese, to make it clear people would notice the scene. I don’t know if he felt sorry for us or if the fun was over, but he called everybody off and they headed out.
    The next morning before he was even fully awake, my boyfriend was apologizing. And then I never saw him again. lol




    6
  48. Kirstjen says:

    When I became single about two and a half years ago after 31 years… I dated like a fiend. I was not nearly picky enough.

    I had a date that lasted 7 minutes. I walked in, sat down, started the whole small talk thing, and the guy looked at me & said, “I just want to face fuck you.”

    Um ok. Date over.

    He texted me as soon as I walked out, apologizing. I told him that he needed to work on his marketing plan.




    13
  49. Katy says:

    Wannabe movie director in LA, son of a minor director. We were going to go to a rave in Lake Havasu, about three or so hours out of LA to do research for his movie. I was hesitant but convinced myself that I was being my usual introverted self and needed to get out and have an adventure. He was over three hours late picking me up and instead of just us two, he brought along three other people, producer types. And then another carload of people joined our caravan. Finally arrive around midnight. While waiting in endless line to park three miles away, I got bored and popped a jelly belly in my mouth. Date grabbed the last few and ate them. I said something about him taking them all and he spit out the jelly belly mess and offered it to me! I decline and he would not stop trying to get me to eat his handful of disgusting ABC jelly beans, holding it up to my face and trying to get me to eat it out of his hand. It escalated to him yelling “EAT IT!!!” and me yelling “NO!!” This went on for at least a minute. Finally he says that he will eat the jelly bean I have in my mouth right then. I called his bluff and took the candy out of my mouth and hold it up to him. He actually took it from my fingers and put it in his mouth and chewed and chewed, nodding and looking at me like “See! I can totally eat this and it’s fun and amazing and you are missing out.” The nightmare date lasted until about 2pm the next day, because the producers couldn’t do research without taking a tab of ecstasy at 2 am. On the way back to LA, the guy driving said that he thought we should just head on to Vegas and everyone agreed that was a good idea, but somehow we never did make that turn. Thank God. When I finally arrived home the next afternoon, the date asked me if I wanted to go see a movie later. I was speechless that he thought I might ever want to see him again.

    I went out on two dates with another guy. He brought Bob Saget with him each time. This is not a code or a joke: Bob Saget sat next to me on both of these dates. Bizarre.




    12
  50. Kathy says:

    From age 18 to 20 or so I dated like crazy. For part of that time I had two jobs–I worked 5 days a week as a grocery store cashier, and 5 nights a week at a Dunkin Donuts midnight to 6am. I figured I could sleep when I was dead. My Dad, stepmother, and I were about a week into an attempt at the Atkins diet. A cute, rich (!) guy I met at the donut store asked me out. He took me to the Rusty Scupper, a pricy seafood place on the water in Baltimore. Trying to stay on my diet (I do not know why–I was far from chubby!), I decided not to eat anything!! I did succumb to the famous freshly-baked brown bread–I guess I was desperate for carbs–and ate two little slices with sweet butter. We talked and laughed and drank. I think I drank a wine cooler. We left the restaurant planning to go somewhere–we’d talk about it en route in the car. Next thing you know, I’m waking up. In front of my house. With my head on my balled up jacket on cute guy’s lap. I have zero memory of what happened, but he gently informed me that about a minute out of the parking lot I planted my head on his lap, immediately fell asleep, and could not be awakened. He let me sleep on his lap in front of my house for a couple hours before he could finally get me to wake up. Very sweet guy–a real catch. Never heard from him again. I guess I did actually need occasional sleep.




    5
    • Kathy says:

      Oh, god, I just remembered my very first bad date. It was my first date ever! I was a sophomore and he was a senior in my English class. He wasn’t even very good-looking, but he was charming (slick!) and a senior, so… One Friday night my friends and I went to an illicit bonfire party. He was there, gave me a big cup of Riunite (not on ice, sadly), flirted like crazy, and asked me out. We went out to the movies that Saturday, and after that–naturally–parking. I got in the back seat with him expecting some snuggling and kissing. What I got was a wrestling match with a horny, very determined octopus! I spent about 5 minutes aggressively blocking his grabby mitts before he yelled, “What’s going on with you? What did you think this whole date was about??” Then he gave me a mini lecture about how I was no fun, and I needed to grow up, and maybe he should just take me home. By this point we were back in the front seat, and I yelled (about 6 inches from his face), “YOU BETTER TAKE ME HOME *RIGHT* *NOW*!!!” I think I actually scared him a little–up till then I guess he thought I was a sweet, naive little girl he could manipulate. Wrong! At my house, I told him not to get out of the car, I’d walk myself to the door. For the rest of the semester he barely made eye contact with me. Chicken.




      3
  51. Heather says:

    These are GREAT and many of them would be fun stories for The Moth… just saying!




    2
  52. Mary Alice says:

    I’ve come back to see any if any additional stories have been posted, and I’ve been reading them out loud to my husband. This is so good!




    4
  53. Amber says:

    1)His girlfriend showed up.

    2)The woman he was having an affair with showed up.

    3)I kissed another guy.

    4)I got dumped in Harlem and was too broke to get a cab so I could cry in privacy. The subway was crowded and I did not stop crying until I was in Brooklyn.




    1

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