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 in order to win a free year of FOCUS Coaching.

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 FOCUS Coaching

Awkward people are commonplace.

Sexually backwards 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.

Without further ado, here are the Top 10 Finalists for Worst Date Ever.

Remember, you only get ONE vote, so choose carefully.

The Top 3 vote-getters will get a year’s worth of FOCUS Coaching, which includes:

  • Access to my bestselling book, Why He Disappeared
  • A monthly interactive Q&A with me on a specific dating topic.
  • A Community with hundreds of other smart, strong, successful women.
  • A Forum where you can ask me your most pressing relationship questions.
  • A monthly CD/newsletter recap shipped to your home each month.
  • Discounts on all of my products: e-Cyrano, Finding the One Online, & the Inner Circle.

FOCUS Coaching is $47/month, which is an incredible bargain for the personal attention, insight and value you receive.

The Top 3 winners will get an entire year of FOCUS Coaching for FREE.

Click here to enjoy a laugh and vote for the Worst Date Ever, to give 3 women the gift of a lifetime!

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


  1. 1

    Thoughts From A Guy —

    I read all 10 and all them had a common theme — weird behavior sprung on the women out of nowhere (it happens)

    BUT about half of them could have been avoided by THE NO. 1 RULE OF DATING / FIRST DATES – ALWAYS MEET IN A PUBLIC PLACE.

    4 of the ten had women going to an isolated place on their FIRST DATE with a stranger (his loft, her place –WTF!!!!??? — and allowed him to SLEEP OVER??? — a boat in the middle of water, the dude’s buddy’s house), most often willingly.

    They are lucky they just had a bad date — it could have been much worse.

    Women need to practice saying this sentence, “I’m sorry, I’m not comfortable with that.” He tries to convince her. She needs to keep repeating it. Again and again. Even in the mirror at home.

    There’s a monologue in GIRL WITH THE DRAGON TATTOO that has stuck with me — people allow politeness / being socially awkward to override their survival instincts / their gut…. something to think about.

  2. 2

    NOT being socially awkward rather

  3. 3

    I read all the stories, and honestly, the whole time I was waiting for something that would beat out guys ejaculating on a first date. I’m a bit disappointed on that front. I want to read the other stories too!

  4. 4

    OMG These are great stories in the top 10 !!! would make a good mini book like Chelsea Handlers My horizontal life
    Thanks for the entertainment!!

  5. 5

    Excellent point David!! I noticed that too I love you Dragon Tattoo quote.

  6. 6

    So hard to choose one! david had good comments. I think we try so hard to be polite, at what expense?

    These are way stranger than my 3rd date w/ a guy (who I knew was not going to be my bf, but we played cards and pool, so it killed some time 🙂 who was taking me on a tour of his house when he told me the reason his parents’ bedroom was EXACTLY the same as when they passed away was “in case they came back’. Oh my…

  7. 7

    Michelle, LOL that is indeed awkward.

    @ David, I totally agree. I am big on safety first, insist upon talking to a guy on the phone before meeting, meeting in a public place near my home, having a date check in buddy I can text while on the pretext of going to the ladies room, and over all, listening to my gut. The guys who got upset about my needing to feel safe, I didn’t go out with. A few of them had some choice words for me for sticking to my guns about safety, to which I just replied, “I need to feel safe. I’m sorry you feel the need to be nasty. Have a nice life.” But I’d rather be considered a “witch with a capital B” and be safe, than polite and sorry.

  8. 8

    I agree with David – I voted for the only one where the woman didn’t meet a first date at a private place. It’s just not a smart move and lends itself to “an awful” first date. Fortunately, nothing more serious happened.

  9. 9
    Happy Person

    If you’re a woman you can’t win with this one. Examples:

    1) I was really raked across the coals by a roommate once, with her calling me selfish and inconsiderate. Why? I didn’t offer a ride to a guy I’d just met (through a mutual friend) who liked me but had been left behind by his buddies at the bar (talking to me). They assumed he was hooking up. He lived an hour outside of the city in a very rural area. I have no idea how he got home and I didn’t ever go out with him.

    2) An ex was outraged that a cleaning company wouldn’t send just one woman to his apartment–they had women work in pairs if the apartment was inhabited by a single male. He thought they were accusing him of being a rapist and that their policy was discriminatory.

    On the flip side, I’ve had a couple of men think I was some kinda you-know-what because I invited them up to my apartment at the end of the first date. I was really shocked by that interpretation of an innocent offer of hospitality (coffee, a drink, nothing else in mind). I still get angry when I think of their misinterpretation of my intentions.

  10. 10

    @ David

    Cannot agree more. There is the problem of believing every bloke out there is a nasty SOB, which is a highly negative attitude, however there is nothing wrong with being careful, keeping yourself safe and maintaining a casual form of contact.

    These are so funny Evan. I must admit the Cat one had me laughing the most, the dildo one came a close second. 🙂

    The only thing better, would have been a fading out voice on the phone “I’m a bad cat, a very bad cat…”…lawls!!

  11. 11

    @ Happy Person, yes, I certainly understand where you’re coming from! I was treated very disrespectfully by a guy, simply because I wouldn’t let him come in the house after a date. I could tell he had one thing on his mind and I wasn’t into that. He acted interested in a second date but then left me a really disrespectful voicemail about how “he met someone else in a bar” and was interested in pursuing things with her instead. The best part was, in between chuckles, he said, “I hope you don’t hate me, haha.” Seriously? I went out with you once. You proved to me what your true colors were. Whatever.

    I had another first date get mad when things got a little too heated and I backed off. He accused me of “mind f*cking him.” The best part was that he showed up on another dating site, months later, and sent a message saying, “Hey, I remember you. 🙂 ” I emailed him back and said, “Yep, I remember you too, you accused me of playing games with you. Do not contact me again. Thank you.”

    Sadly it can feel like a damned if you do, damned if you don’t scenario with some first dates.

  12. 12

    I’ve read on other internet forums if a woman invites a man to her place, or agrees to go to his, it is implied she will be having sex with him. Not just the first date, but any date. I was surprised to find out how many people accept this as “common knowledge”.

    With previous partners, we spent a lot of time hanging out talking, eating, watching movies at our homes as part of getting to know each other. Makes me sad that people feel they can’t date that way these days until after they’ve had sex.

  13. 13

    @Selena 12

    Not everyone thinks that way. The easy solution is to spell it out. “I want to hang out at my place/your place. This is not an invitation to be physically intimate, just an invitation to hang out in a relaxed environment.”

    I think the people who assume that are the same people who are causal about having sex.

  14. 14
    lux aeterna

    I think this contest should have been split into two categories: funniest [in hindsight!] and scariest. I felt almost bad for choosing the most entertaining story over the more serious ones [boat and theft]. Of course it’s obvious that a date that puts your life, health and belongings at risk are far worse than having to spend a few hours with an insulting, boundary breaking psycho. But, I love a giggle, so comedy won for me…

    Like everyone, I have stories too. Not juicy enough for this contest but still, here goes:
    I know full well that medical issues are not a good topic for first date conversation, but it was springtime, my hay fever was out of control and I just had to say something about my sneezing and runny eyes as a brief explanation straight after introducing myself. ‘Oh I have allergies too!’ says Mr. Date with great enthusiasm, and goes on to describe his eczema and various rashes in detail. Then the ultimate date-killing bombshell: ‘I have latex allergy…!’ Aha, I said, nodding, as a hint that yes, I understand where that would be problematic, and let’s leave that topic unexplored, shall we? Hint was not taken, and he ventured on to describe his manhood and how it would grow… and swell… and go red… and itchy… while staring at me intently and touching my leg.

    I have another story too, where a scenario turned violent with a very real threat of rape, but Evan has asked to keep this fairly light hearted so I’ll save that story for another time.

    I agree with other posters here, that us women have to learn how to say firmly ‘Im not comfortable with this’, and a lot of bad scenarios can be cut short. I’m just as bad, brought up to grin and bear it, not cause a scene, be polite etc. I now have an agreement with myself where I acknowledge this programming and that I might not show my reaction straight away. I do however make sure I let the culprit know of my discomfort with a situation even if it’s several days later. Better to say something than say nothing!

    As for inviting people in after a date, I have done that on occasion but said loud and clear that it is a real coffee invitation, not for sex or staying over.

    Oh, and as a bonus, pleeease share the ejaculation stories, Evan! Maybe in an email for us who beg the most? 😀

    1. 14.1
      Evan Marc Katz

      @Lux – No need to post 3 ejaculation stories. You already know the climax. 🙂

  15. 15

    @ SalsaQ

    Don’t you think it’s a bit sad (not to mention a little awkward) that anyone has to spell it out? That’s what I’m talking about. It should be perfectly reasonable to ask someone you like, “Hey, would you like to come over and hang out? I’ll throw some steaks on the grill.” Or, ” How about pizza and a movie at my house tonight?” Without sex being “expected”.

    I’m not talking about a first meeting ofcourse, but during the first few weeks when you are trying to get to know each other. I don’t know, maybe it’s just the forums I’ve been reading, but there seems to be a kind of a rush to get to sex by spending minimal time together. All these expectations, 3rd. date sex, don’t go to anyone’s home if you don’t plan to have sex, reinforce that mentality.

  16. 16

    It was so hard to pick just one. I think they all equally “sucked.” 🙂

  17. 17
    Happy Person

    @15: But not the details!!

    This feature is really fun and funny. Hope you have more like this.

  18. 18

    Re: #18
    I agree! It may be schadenfreude, but reading bad date stories makes the whole dating process amusing.

    Evan, you might consider making this a semi-regular feature. Lighten up the blog from time to time. 🙂

  19. 19

    To the folks concerned about the “Deadliest Catch” sleep over issue and safety concern: He had driven from 4+ hours away and it was a nor’easter. The storm had escalated and I offered to let him crash on my couch, rather than get into a car accident just trying to leave town (the roads weren’t even plowed). So there were extenuating circumstances. We met in a public place and had been chatting on the phone for 6 months prior to this date. Otherwise, I never invite a stranger to my place for a first date. I’m also former law enforcement and live next door to a state trooper, so that was a factor in my rationale. I was not really alone/unsafe.

  20. 20

    I hate to say this, and I really don’t want to pour salt in anyone’s wounds, but you still, well, got robbed. Your law enforcement history and your neighbor didn’t / couldn’t prevent that. And chatting on the phone for 6 months? But I am sorry you had that experience.

  21. 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

  22. 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.

  23. 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.

  24. 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 🙂

  25. 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?

  26. 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”?

  27. 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?

  28. 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?

  29. 29

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

  30. 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!!!)

Leave a Reply

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