Your Worst Date Story, Ever!


The dating biz is a small one. Pretty much everyone who gives dating and relationship advice in the U.S. is someone with whom I’ve crossed paths at one point in time, and most of them are pretty darn good people. A perfect example is my friend, Jennifer Kelton, who is the founder of

Find humor, catharsis and knowledge in sharing these kinds of experiences.

Although it sounds negative, Jennifer finds humor, catharsis and knowledge in sharing these kinds of experiences, and she’s giving you the chance to participate. Just send her your best worst date story through and have a chance to win a $50 gift card, a ”Worst Date Ever” tee-shirt and the online coverage of your story on

Click here to learn more.

As for me, I won’t be entering because it wouldn’t be fair.

As a veteran of 300 online dates, I have at least 5 that would trump your worst date, and virtually make your head explode with some version of “She said WHAT?!” Don’t even test me. I’ll win. 🙂

So please, share your worst dates with me in the comments section…then swing by Jennifer’s site and win something for all your pain:

Join our conversation (33 Comments).
Click Here To Leave Your Comment Below.


  1. 21

    Wow, I don’t feel so bad about my worst date story.   The guy was saying “I’m in love with you” on the phone before we’d even met.   I did give him the benefit of a doubt and met him for dinner.   When the conversation turned to his sebaceous cysts, I saw my life with that guy flash before my eyes.   Needless to say, that never happened.  

    All guys are not bad.   Somewhere out there are some great ones.   But the bottom feeders just make my head droop.

  2. 22

    On the commitmentphobes: I think everything in our culture points to women as disposable commodities to be consumed and upgraded, discarded, collected and traded  like coins, watches, baseball cards.
    The whole women with cleavage, airbrushed images on every corner–what if we did this to men and made them wear make-up, and be a fantasy sex images to us–for the most part they do not play this role.  I hate saying this, as it’s so blatantly obvious, we overlook it as a given.
    My main point–male promiscuity is celebrated and seemingly more gratifying (reality- not as pretty), than for women due to power dynamics–women are seen as softer, less threatening, catlike and soft, emotional, and men are seen as more dominant and withholding.
    So, what is in it for men to commit, unless they reach an age of fewer options, desire security or want kids? The fantasy for men is to be irresistible to all women, it’s not to be married.
    The coming on strong is simply the need to conquer. I’d say don’t let yourself be conquered. They will go away unless they really like you, and at least you wouldn’t be taken on a ride. One can choose to take it slow, keep oneself sane for the keeper,  who will eventually turn up.

  3. 23
    Evan Marc Katz

    @Mora – wouldn’t disagree with most of your points – there is a problem with male promiscuity and entitlement – see Maureen Dowd’s column today; however, I entirely disagree with your conclusion:

    “Don’t let yourself be conquered. Your keeper will ‘eventually’ turn up.”

    Sorry. If you follow that strategy, you are correct that “they will go away”.

  4. 24


    Just curious- your reply to Mora’s “don’t let yourself be conquered.”

    Why is it a ‘bad’ strategy? I’m assuming Mora’s saying, don’t stray from your principles and who you are as a person when she says that. You can’t possibly be telling us we shouldn’t do that, right?

    I might be misunderstanding something here- if so, plz feel free to clarify.

  5. 25
    Evan Marc Katz

    @Sayanta – Men ask you out, they follow up with phone calls, they pay for you when courting you, they ask you to be exclusive, they ask you to sleep with you, they ask you to trust them – this is what they do to “conquer” you. If you aren’t receptive to this – or put up walls because you believe that men exist merely to “take you on a ride” – lots of good men are not going to want to climb your walls.

  6. 26

    So I just had a guy contact me again after weeks of no contact, but let me rewind to why.   He started from being in love and ready to put a ring on my finger in 6 months to our final conversation which was pretty much him throwing ad hominem attacks at me.   I only saw him once during that roughly 2 month period.   He got his final word in and I thought fine, won’t have to hear from him again.   Tonight, he decided to try fence testing.   Can’t say I was really open and receptive.   Had I forgiven?   I guess so, as in after that last ugly conversation, I didn’t give him any thought.   I’m guessing the only reason he contacted me is because he’s got nothing else going on.   Not that I do, but I’ll take my Friday and Saturday nights at home alone over that drama.

  7. 27

    You definitely have more options than just “home alone” or “that drama.” Get out there! Don’t let one fool get you down… I love some of your phrasing, BTW. The “rewind to why” and “fence testing” are awesome.

  8. 28


    What an ass…I think the God/dess is protecting you there (if you’re atheist, change that to…”it’s for the best”).

    I actually initiated contact with a guy a week and a half ago- got no response, until yesterday. He said he’s just started seeing someone (yet he’s very active on Match), but he’d really like to get to know me better and be ‘friends.’ Um…ok. I hit delete on that one.

  9. 29

    @ Cat,

    I don’t deny that there are alternatives to sitting at home alone on Friday and Saturday nights; however, when you live in central Illinois,   there aren’t may options other than the bar scene or spending Friday and Saturday nights at the Barns & Noble.   I’m also finishing up my BA and working on getting into a MPA program this fall, which I’d like to finish in about 12 months so I’m going to have to have a laser-like focus on that, as well as work full time and raise three kids.   I’m very aware that there aren’t going to be many men wanting to share time with all of that.  

    @ Sayanta,

    I am convinced that this dude has a personality disorder.   Not just because of his treatment of me, but of some other observations.   A narcissistic misogynst cannot be reasoned or dealt with.   You just run from it as quickly and as far away as you can.

  10. 30

    Went for a couple of drinks one evening with a guy I’d been chatting with on an online dating site. I’m not the sort of girl who needs to be pandered to, so we drank in rounds- buying each other drinks. We got along well but as this was the first encounter nothing happened- not even so much as a kiss.
    upon leaving work the following evening- I work in a basement of a building with no phone network for shifts 12+ hours long- I had six text messages and three missed calls from the guy.
    his ultimate response to not having heard from me for 13hr was that he wanted me to repay him the money he had spent buying me drinks seen as I had been leading him on…

  11. 31

    OMG GB, what did you do? Did you block him?

  12. 32

    So I started talking to this guy on a dating app. We exchanged numbers and we had a lot in common… I was really feeling the guy. His schedule was the opposite of my schedule so it was very difficult planning a date to see each other. We texted and talked over the phone for 2 months everyday. So finally I asked him about a date that I was available and asked if he was too and he was after work (7pm). He told me his car needed new tires so I would have to come meet him(he lives in the city SF, 45 minutes away from me). I told him I was cool with that but since I was going to meet him   I suggested he should plan the evening since we would be in his city. So I drive to his place and called him that I was there. He picks up and tells me if I could wait because the game was on and that it was on fire I was like wtf. I parked my car and he walked me in his house and I met all his roommates all 6 of them… they introduced themselves to me…. Anyways he didn’t have anything planned for our date. He was conversing with his roommates and looking at his computer to keep up with the score of the game as I was just sitting there. So I told him we could go eat somewhere that has the game showing   … his roommates were suggesting places where to go eat…. so we decided LAST MINUTE where to go and then he changed his mind LAST MINUTE to going somewhere he wanted to eat …. fast food burrito place. I PAID because I’m a moron. After eating we sat in my car by his house and talked for 30 minutes and that was the end of it. Im mad because what a waste of 2 months of talking and what a waste of me getting dressed up for an asshole

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