The Top 10 Worst Dates Ever


After 9 years as a dating coach, there are times that I’m tempted to say that I’ve heard it all.

But I’ll be the first to admit, I hadn’t heard anything until I asked you to submit your Worst Date Ever.

I know you’re excited to vote on the Worst Dates Ever, but before you do, take a second to read what you can learn from other women’s laughable experiences.

1) Men are pervs.

Now this isn’t news. In fact, a central tenet of my dating coaching philosophy is that “men look for sex and find love”. Yet the number of men who moved too fast physically literally DOUBLED any other type of worst date.

Here’s the tally, from over 200 submissions:

  • Moved too fast physically – 33
  • Didn’t look like photos/lied about age — 15
  • Cheap — 15
  • Forgot wallet — 9
  • Hit on/commented on other women – 9
  • Moving too fast emotionally — 5
  • Drunk — 4
  • Abandoned you — 4
  • Emerged naked from bedroom — 3
  • His ex-girlfriend approached you on the date — 3
  • Ejaculated on you — 3

Amazing stuff, huh? While there were some really over-the-top dates in the above categories, none of them can be the winner.

After all, how do you choose between three DIFFERENT instances of men surprisingly ejaculating on you when you weren’t even getting intimate?

That’s right. You can’t. The 10 Finalists are even freakier than the above entries.

2) Cheapness really, really, bothers you.   

If a guy doesn’t pay for the check, you’re not only turned off, but it somehow goes down as the worst date in history.

I can appreciate the notion of chivalry, but until you’ve had a guy unknowingly jack off on your pants, getting stuck with the check doesn’t even put you in the same ballpark as our finalists.

3) What didn’t qualify for the Top 10:

If someone else had the exact same story as you…
If your nightmare date resulted in a boyfriend. (This happened a few times)
If it was genuinely threatening. This is supposed to be a light-hearted contest where we can laugh at the embarrassing foibles of clueless men. Some of your bad dates sound like police reports. So while they’re awful, they’re also big downers. Sorry, but it’s not the right tone for this contest.

4) What you can learn without even joining Love U.

Awkward people are commonplace.

Sexually backward men are commonplace.

Bad dates are commonplace.

Not my opinion. Fact.

So, while I think it’s wonderful that we can laugh at this stuff together, I was dismayed at the number of women who confided that they gave up on dating or online dating or men, simply because of one date with a freak.

I’ve said it before and I’ll say it again: giving up on dating after a bad date is like going on a hunger strike after a bad meal. It’s short-sighted, it’s dangerous, and it will never leave you satisfied.

The next guy has nothing to do with the last guy.

Laugh it off. Move along.

That’s literally all you can do.

Click here to enjoy a laugh and vote for the Worst Date Ever

Join our conversation (32 Comments).
Click Here To Leave Your Comment Below.


  1. 21

    @ Lux #14, ahhh latex allergy, oldest line in the book, along with “my wife and I haven’t had sex in years”… Gotta admire those guys’ hope that, maybe this time, it’ll work. LOL

  2. 22

    @ Goldie, HAHAHA!!!! Yes, I heard that one a lot. That one cracked me up. I used to get a kick out of it after awhile. I’d email them back and ask them if I could tell their wife what they told me. The result was…..wait for it….silence. LOVED it.

    Another one that had me almost in tears from laughing, was a guy who emailed me and said that he was divorced, but he and his ex wife worked in the SAME SCHOOL. Uh, say what? I asked him why they both worked together if they were divorced. He said that neither of them wanted to move to a different school. I’d heard enough. I said thanks, but no thanks. He said well, my ex and I are definitely not together, but I understand your concerns, other women have turned me down for the same reason. I about died laughing. I thought OK so if he’s getting this feedback, um, shouldn’t he DO something about it so he can meet somebody? I guess he really didn’t.

  3. 23


    Maybe his career happiness was more important to him than meeting someone. It is just a different priority set. Also, just because some other women have given him that feedback, it doesn’t mean they all have. He has probably dated women who are secure enough that they don’t care if he uses the same lunch refrigerator as his ex wife.

  4. 24

    These are all pretty funny, and a few of them are rather frightening. It definitely makes me feel better about my worst dates. Well, there was that one guy who turned out to be…never mind…another time 🙂

  5. 25

    The craziest thing for me about these awful date stories is that i have BEEN on several of these dates!! I have been on “butt out ” date, and I have dated the cat guy… I don’t know if I’m relieved or freaked out that there are other “cat guys” out there….!
    As for “come up for coffee” being an invitation to sex… come on girls, its the oldest euphimism in the book! I actually get annoyed by women who come out with these so called “date rape” stories that go “I just invited him in for a drink then suddenly he started trying to undress me…” If you don’t want a new guy to undress you what on EARTH are you doing inviting him in to your apartment?? What are guys meant to do, get a written agreement before they make a move?

  6. 26

    I wouldn’t invite a guy to my place on the first date, but I’ve invited a few to come up on the second or third. None of them automatically assumed that meant sex, and none of them ever tried to molest me. Actually, I did once invite a guy to come up and wait for me while I got ready to have a first dinner date with him. He definitely wanted sex, but backed off when I said no.

    Sorry, but inviting a man over isn’t a tacit invitation to commit rape. Forcing a woman to have sex against her will is never acceptable. Whatever happened to “No” means “No”?

  7. 27
    Happy Person

    A guy who thinks that going into a woman’s apartment means sex needs some lessons in seduction and in how to please a woman. Because that isn’t what it means, so he has a problem reading women’s behavior accurately. If he can’t get something that basic right, how is he going to get the trickier, more complicated sex signals right?

  8. 28

    I had to laugh at this article. I had a date that wasn’t the absolute worst for me but was the absolute worst for my date. There are peals of laughter ringing out of me right now just recalling it. Years ago I used to work in the corporate world in Manhattan, and right downstairs from my building was this little deli where everyone would go to grab a snack or lunch. It seemed everytime I went there I would see this same guy and after a time we started a conversation and eventually went on a date. He took me to a really nice restaurant and then we went dancing and had a really good time. On the way home in his car I started feeling sick (I later came down with a full blown case of the flu) and had put my head down to try to contain my nausea. I happened to turn my head and saw that he had his pants zipped down with his penis out and was whacking off and just at that moment a gusher of puke flew out of my mouth all over him. He was totally covered from the waist down with vomit but I didn’t get one drop on myself. I started screaming at him to pull over because I felt like I was going to throw up again. As soon as he did I jumped out of the car and hailed a cab and went home. I avoided that deli for some months after that and one day was with another person when I saw him across the street (fortunately, he didn’t see me). The person I was with knew him and said that he was a married man and a philanderer, and that his wife was the sweetest person she knew who seemed to be the last to know. Up to that point I had no idea he was married. I always wondered, since his pants were opened at the time of the incident, how he explained the vomit inside his pants to his wife?

  9. 29

    I see that only women were asked this question. I bet that men would also have some interesting answers.

  10. 30

    Kurt 30 – That reminds me of a poor man’s predicament which happened in real life.   He was a passenger holding flowers for I assume his wife (nicely dressed man – complete “normal” and I was behind him, made up for the evening, deep red lipstick and we were travelling on the subway.
    The transport braked, I fell on to his collar, leaving a deep red lipstick mark.   I DID try to tell him, oh God, I’m sorry, I…… but he thought I was coming on to him.
    God knows what kind of evening he had with his wife!!!! (or girlfriend!!!)

  11. 31
    Jenny Ravelo

    All the stories where very funny, seemed as if they were written for a comedy, but the story “Squashed” was pretty sad.

Leave a Reply

Your email address will not be published. Required fields are marked *