What’s Your Dating Nightmare Story?

I want you to tell me about the WORST date you’ve ever had.

Not the one where he didn’t pay the full check or the one where he talked about himself for 90 minutes. I want you to tell me the funniest, weirdest, most over-the-top bad dating experience you’ve ever had.

It can be a video, in an email, or in an audio — whatever is best suited to telling your story. I just want you to be able to share your pain with other women — so we can all get a mutually cathartic laugh out of it.

Alas, I’m not doing this just for laughs.

I’m doing this for YOU.

After all of the bad date entries come in, I will choose my top 7 and post them for you on my blog. I will then ask you to vote for your favorite, starting on Monday, May 8th.

When voting closes, the top 3 vote-getters will get… Free access to my FOCUS Coaching for an entire year!

If you didn’t already know, FOCUS Coaching is my comprehensive, interactive, affordable coaching program where I choose a new dating topic every month. Sex, Flirting, Being a Great Girlfriend, Overcoming Negativity…just some amazing, juicy topics that give you powerful tools for dating success.

In FOCUS Coaching, I do a live Q&A, taking questions from you for an hour. At the end of the month, I send you a CD/newsletter recap in the mail. In between, you get access to my exclusive member forum, where you can ask me dating questions and receive support from hundreds of other women around the world.

FOCUS Coaching is normally $47/month.

I’m giving that to the winner for 12 months.

That’s $564 in retail value — or about $5000 in coaching value — absolutely FREE.

Just share your dating story by Sunday, May 6th and may the worst date win!

Thanks so much for your willingness to listen, your desire to learn, and your ability to laugh at all the things that can go wrong in dating.

Share your worst date story below:

Update: Story submissions are now closed! Thanks for the hundreds of responses I received, I’ll be announcing the Top 7 Worst Date Stories Tuesday, May 8th. I’ll be sending out updates via my newsletter, so make sure you sign up to get the latest updates and free weekly dating advice.

Join our conversation (30 Comments).
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  1. 1

    This wasn’t the worst just the most hilarious!!
    So it started out with txting..I’d ask a question, his answer was Yes, No, Maybe. That should a been my clue, right? We set up a time to meet.
    I walk up to him, He picks me up and says “Ya”. WHAT? hum, I guess that was a good thing.
    It’s after work so I had heels on, white pants…good thing a coat. He says “My friends just bought a place and wants us to come eat with them.” I say “I thought we were meeting for a beer?” I’m a gamer and say sure. Well, he shows me our ride. It’s from the era of Hitler(no really, he collects and restores them) a motorcycle with a rickety side car. I get in, he gives me a helmet. I keep thinking what if the side car falls off…and off we go. It’s only suppose to be down the street of Old Town Temecula, the blocks keep wizzing by, I’m thinking I could jump and still be okay. We pull up to this apartment, can’t get in the front gate so we walk thru shrubs, in the dark, upstairs to their apt. I am introduced to a wife who is texting and won’t look up, in the chair at the table is a guy who is beyond wasted and then the husband. He’s hilarious and has us both laughing. NO dinner, a bottle of water and trail mix! We leave. He wants me to see his place so I “get him” by this time I sense he isn’t a perv, just a real guy. Rolling up to his place he says Hold my hand, havn’t had time to clean up the dogs mess! Oh crap!, We enter thru the kitchen…omg…Now get this, he is a fireman and has 4 days on, 4 days off. Plenty of time to clean, mow the lawn, etc…The house is filthy, we work our way to the back yard… Lets have a bon fire…no thanks I got to get home to feed MY animals. A short bonfire it is!! “Would you like a glass of wine?”, I say sure, as I keep moving my chair back because the fire is soooo hot and dogs are licking and wanting to be lap dogs, hoping I don’t by accident put my foot in doggie doodoo, or get knocked over by dogs. He comes back with a glass for us to share…lmao! No problem I can share. He’s a fireman and I thought he was going to torch his whole “f”ing neighborhood. Dried Christmas tree with a 12′ oak pallet thrown on top…kinda not even in the firepit…lol. It did melt the basket ball hoop! He walked me to my car. Again picked me up, kissed me on the cheek and off I went. I drove home, knowing this is a story for the telling! (no names) because I know he’s a good guy. He is not for me.
    I always text after I get home to thank them for meeting me, etc.
    Next morning He texted “Yep, I like ya”…

    1. 1.1
      Evan Marc Katz

      @Gayle – Thanks for the funny story, Gayle, but you have to submit your bad dates via the form above to be considered eligible for the contest. – EMK

  2. 2

    Can people write their funny dating stories on this thread anyway? Some of us need something to read besides the vanity thread. 😉

  3. 3

    Gayle, this one was good! I have to say that I needed a little humor today and enjoyed your story………..

  4. 4

    Do we get some sort of notification when our story is received?

    1. 4.1
      Evan Marc Katz

      Your story was received, Erin. I can say, definitively, that people who use the audio or video version will have a leg up when it’s time for readers to vote. It’s not just whether you had a funny thing happen on a date – it’s how you tell the story itself….

  5. 5


    Oh I have one for you. I won’t submit it for the contest but if you want a giggle, here ya go…..

    So this was 2006. I’d separated from my now ex husband, had my legal separation paperwork in place. So I decide to kind of wade into the shark-infested waters of the Washington DC dating scene. I responded to a personals ad on Craigslist, the guy was very upfront about not wanting kids, and I admired his honesty.

    So we correspond. I give him my number and ask if he wants to talk. Suddenly he’s “not a phone person.” Hmmm. OK. I thought something was odd but I thought well I just came out of a bad marriage, try to keep an open mind and don’t start thinking all guys are bad.

    I’d seen a picture of him and he looked nice enough in the photo. We agree to meet near a subway station. I see him come up the escalator…..he’s walking all hunched over, wringing his hands…..and wearing this god-awful outfit, yellow striped polo shirt, long khaki shorts, hiked up socks and sneakers. YIKES!!!! Oh and he’s got tattoos all over his hands. He never told me about that. He got up right in my face and asked if I was Heather. Stupidly I said yes. I should have lied and run outta there.

    We went to dinner and he started telling me stuff that was just odd (was on paid leave while his clearance was being re-investigated. Turns out they only do that if you’re really sketchy, and my brother has a top secret clearance, so I knew this guy was wacked) and starts talking about how he’s done naked sky-diving. EEEEEK!!!!!

    Luckily dinner was brief. He asked me to figure out something else for us to do, and I pleaded off, saying that I needed to get up early for work (which actually was true). He was really making me uncomfortable so I high-tailed it for my subway platform.

    I got home and sent a polite “nice to meet you but I don’t think this is going to work out, best of luck” email. I got a very angry, “What do you MEAN this won’t work? Call me.” I thought first off, whoa, anger issues, my ex is an abusive rageaholic, heck no. Second of all, you said you weren’t a phone person. I just emailed back and said, I’m sorry, but this is not working for me. He emailed me several more times, and I finally had to say, OK you know what, enough. Keep emailing me, and I will contact the authorities and you can then basically kiss your clearance goodbye, ok?

    He finally got the hint. I actually ran into him a year later at a Meetup group event, and I had my then-boyfriend with me. The guy took one look at me, and ignored me the whole evening, LOL!!!!!

    He was scary to me at the time, having just come from a violent marriage, but now I get such a laugh out of it. I tell that story to some guys and say, see, we girls do not have the corner on the needy and psycho market, LOL!

  6. 6

    I’m happily married, so not entering the contest. My worst date would have to be the guy in his late 20s (I was 40) who came over to my house for a drink, told me it was the ugliest house he’d ever seen and suggested that I burn it down and collect the insurance money so I could build a new one. He was serious, and even gave me some arson pointers. (#1 tip: don’t use gasoline, ’cause he saw on T.V. once that the firemen can figure that out.) Way to impress a lady and show off one’s dazzling I.Q.! (He also couldn’t understand why I wouldn’t want to go out with him again, simply because he’d insulted my home then urged me to commit a felony. Also he was unemployed and living in a rented studio apartment in an iffy area, which I didn’t find out until that evening.) Having read the reminiscences above, I guess I’m lucky this was my worst experience! 🙂

    1. 6.1

      Gosh, you sound so much like when Bonnie Kaye tells the stories of her dad burning down houses…what a coincidence.

  7. 7

    How do I make sure that my story was received?

    1. 7.1
      Evan Marc Katz

      Submit it and you’ll get a message on your screen where the submission box used to be: “Thanks for submitting your story. Keep an eye on your inbox to find out if you’ve been selected as a top story, with a chance to win FOCUS Coaching for an entire year!”

  8. 8
    Saint Stephen

    Men, that has got to be the most funniest worst date story I’ve ever read so far. Thanks for posting,… nearly cracked my lungs with laughter. 😀

  9. 9

    BeenThruTheWars, I’ve had a couple of dates like that. I had a first date last year with a guy who started right in with telling me how much he hated his ex wife and how much she spent in litigation fees to keep primary custody of their two kids. Oh and also how monogamy was/is “a relatively recent concept.” Hello! I think he saw the involuntary look of just disgust on my face and the conversation got a little strained from there. I was so not amused. I thought, I wasted my pretty new Ann Taylor Loft dress, and a Friday night, on YOU?? Yeeeesh!

  10. 10

    @EMK, are you saying that the man should pay for the meal on a first date ? Is it bad manners for him to insist on splitting the tab ?

  11. 11

    @ Daphne, look at it this way. If he insists on splitting the tab, it’s 99 percent sure he doesn’t want to see you again. I’ve learned that little lesson. And it kept me from taking things personally or getting my feelings hurt. I’ve had a few first dates last year before I met my current guy, who asked to split the tab, so I knew it meant he didn’t want to date me again. I just thought, hm, OK, well I could tell by his body language tonight that he wasn’t interested anyways, so that’s cool. End the evening, go home, keep your head up, and go meet someone else, he ain’t worth any pity party or hurt feelings. Once I learned to take control of my own self, it made things easier. Dating will never be easy, but at least it’s easier now.

  12. 12

    Daphne and Heather- GLAD I live in a conservative part of the country and most men with class don’t split tabs here- at all. Maybe on the 5th or 6th date….

    Personally I would find it insulting if a man did that to me on the first date or second or even third for that matter. My feeling is the guy is, at that stage, “selling himself” as Evan has mentioned…..The current guy I’m dating is my age (late 50s), politically moderate for the most part, a Southerner, etc. but I think because he’s really smitten with me, because we are boyfriend/girlfriend hasn’t let me pay for a single date in nearly 4 months! Not meals, not movies, nothing. AND he buys me things he thinks I need.

    The man I dated before then (6 months) was 17 years younger, grew up and in CA and FL, not Southern in his thinking at all, not conservative, but he also picked up every tab, probably because he made 6 figures. Not sure. He never wanted to go exclusive though, so go figure.

    I’ve dated other “Yankee” men here and they did the same thing. But all of them were comfortable or fairly comfortable financially.

    I’ve offered to split, but classy men here in general won’t have it……

  13. 13

    Ive never been on a date since single the last few years where a guy suggested we split the tab. Id be shocked if that happened Im 53 and they have been 35-55 S California I don’t think any guy thats serious about you in a romantic way would have you split.

  14. 14


    Are you serious? That has to be one of the funniest and worst dates I’ve heard in a long time. He probably thought you would split the insurance money with him since he gave you the idea… lol!

  15. 15

    @Gayle, if you’re the type of person who doesn’t like to clean up it doesn’t matter if you have 4 days on and 4 days off !
    If I find a boyfriend, I’m going to have to start cleaning up my house finally.

    @Other posts: Insisting on splitting the tab must mean the guy simply doesn’t want to see you again. (Age 58, California btw). I was a bit shocked but it was obvious we didn’t hit it off.

  16. 16

    *Insisting* to split against your active resistance to pay says something (like he is kind of selfish), but are you women serious?

    Why would you want to date someone who is not up front about how he feels and relies on ‘signals’? Sometimes I have been unsure at the end of the date, but I always, always follow up with a phone conversation if possible instead of just leaving them waiting and waiting forever.

    This “who pays means something” language is risky. I had a steady girlfriend (over a year) get annoyed when I would try to pay for everything. She said she felt badly because it did not seem fair. She wanted things to be 50/50, which I respected and understood, but I also made 3-4 times her salary. It was more practical for me to pay, yet sometimes this became a sore point for her. I certainly let her buy me drinks sometimes and was always beaming when I got a thoughtful present from her, and yes sometimes we did split the tab but this was always kind of a tricky negotiation.

    Every woman and man is different, so when you always assume something like “splitting the bill means he doesn’t want to see you again” or “he said I am pretty, but not beautiful so he is not into me” risks a lot of mis-communication and possibly blown opportunities. Ask for clarity if you aren’t getting it, and if he is not comfortable with that he is not going to be a good communicator later either.

  17. 17

    Some very funny stories!!!! Love the arsonist and the fireman

    Ok this guy contacts me today Seems attractive successful and bright and on his profile it says all dates are DUTCH TREAT (WTF???!!!)

    I clarified why thats important to him …..He normally dates models and he’s concerned they are only after his wallet (….. Yawn!!!!…..)

    Theres no way Im doing my hair getting a manicure, working with a trainer, paying for the gym, my clothes my shoes etc… for this dude who has a problem with buying me a coffee

    Allen I think there is a difference between a guy who wants to impress a woman and pays for the tab vs a woman who insists to pay her own way.

  18. 18

    A man actually put in his profile all dates are DUTCH TREAT?
    My. Normally dates models? Afraid they are only after his wallet?

    If I read something like this I’d be thinking: cheap dude with a rich fantasy life.

  19. 19

    It is funny how Ellen associates paying for everything including buying extra things men thinks she needs with being a “classy man,” even if the guy isn’t her boyfriend. Most men, including myself, would think that a man who does that is most likely a chump who thinks he has to do this or is somehow buying points with the woman. Younger men might start out doing this if they are inexperienced with dating and assume it is required of them, however, as men mature and get taken advantage of by women a couple times, they quickly learn not to do this.

  20. 20

    Im always a bit surprised when I read about how people automatically expect the man to pick up the cheque at the end of the date. I always expect to split it and am fine if that happens. If a man insists I smile and say thanks, but I don’t expect it automatically. I can see why people expected it years ago when women might not be earning decent enough salaries to afford to buy themselves dinner. But these days? I just don’t really get it. I understand about the need for feminine receptive energy and for the man to show he is interested and thoughtful etc but
    I can think of a thousand ways he could show that without having to automatically pay for stuff. Am I the only woman who thinks this? (I’m not meaning this as a criticism of those who likerhe man to pay by the way: each to their own I say. I just wonder whether everyone thinks this (ps I’m in London. I wonder if maybe the rules are different in different countries?..)

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