Real stories about dating and relationships in New York City. Truth is more interesting than fiction.

My "Worst Date Ever"

I get asked about this a lot – My worst date ever.  It’s kind of funny, because until I started writing this blog, I’d never really thought about it.  I’ve had so many bad dates in my life that it never really occured to me to compare the bad against the bad and come up with the winner of the worst date contest.

Maybe it’s not supposed to work that way?  Maybe the “worst date ever” is supposed to be so bad that the second it’s over you know – that was it, no date could ever be worse?  Who knows…

Well, here it is, My Worst Date Ever story:

A friend of mine had mentioned that she thought I might like this guy she worked with.  Honestly, she didn’t tell me anything about him other than that she thought he was cute and that he was a friend of hers from work.  And I figured that if she liked him enough to call him a friend then he must be a good guy.  I told her that I’d be interested in meeting him, so she suggested that I meet them out at happy hour one night.  Which I did.  The bar was insanely crowded and loud (happy hour!) and he and I could barely hear each other talk.  But I guess he thought I was cute because later that night I got a call from my friend telling me that he’d asked her for my number and to expect a call (I’d given her the go ahead to give it to him).

Now, before I get into the date, I should mention that this was a few years ago.  For the last few years I’ve stuck to some pretty strict rules about first dates.  Rule #1 is  never, ever, commit to a meal with a guy you don’t know.  If I meet someone for a drink and it turns out I like them and I want to get dinner from there, fine.  But I never commit to dinner up front.

This is the date that caused me to set that rule.

Fast forward a week.  We met for dinner at a restaurant of his choosing (He’d called and asked me out to dinner, I said yes.  The call was quick and to the point.).  I didn’t know the place, but I knew the ‘hood and was cautious as it’s not an area I usually hang out in (full of pricey, showy places with blah food).  Anyway, I knew I was in for a long night when the waiter came to take our order.  My date ordered several courses of food and a bottle of wine.

It was a long night.  A very long night.  I could tell before the first course arrived that he and I were ill-suited for each other.  He was an ex-frat boy who still hung out with his college buddies and drank to excess on the weekends (I’m not judging).  I didn’t go for that type of guy in college and I wasn’t going to start in my thirties.  But I had a little problem on my hands.  He thought he was charming.  And funny.  And smart.  And he was a friend of a friend.  And while I had decided that I’d had enough of his company about 15 minutes into the date, I had several hours to go before our meal would be finished. I felt I had no choice but to humor him, completely.

Was he a complete nightmare who made me cry in the ladies room? No.  He was a jerk who became more of a jerk as the night wore on and as he had more to drink.  I tried as hard as I could to stay unfailingly upbeat and friendly no matter how tedious the conversation got (the phrase “I was so wasted” featured prominently in most of his stories).  And eventually the night did end.  We split the check (I insisted on spiltting the check) and went our seperate ways.

As horrible as some of my dates from have been, and sure, some have been pretty horrible, I think it’s kinda funny that my worst date ever was a friend of a friend.  I mean, people are always complaining about and how it’s such a bad way to meet quality people and I’d do better with recommendations from friends.  But I think there’s something to be said for going into a dating situation with a complete stranger.  If worst date guy were just some random guy I met in a bar or online I would’ve made a polite excuse early in the evening and left early (leaving my share of the bill, of course).  But I didn’t do that because I felt obligated to pretend I was having fun.  Or try to.

So I guess there are a couple of things to be learned here:

  1. There are no good or bad ways to meet a person,  What matters is what happens after you meet (online or in the flesh).
  2. Dinner really is a bad idea for a .

Or maybe there’s some bigger, more profound lesson that I’m missing?  It wouldn’t surprise me one bit.


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15 to “My "Worst Date Ever"”


  1. Teifion says:

    Sounds like a pretty good rule to me and a good example of the fact that you can take a bad experience as a lesson or as the loss of X hours of your time. I personally would probably have told them pretty bluntly it wasn’t funny (for bonus point, guess one of the reasons I’m single!). And secondly, as a “worst date ever” it’s not _that_ bad, he wasn’t a mad axe murderer or something scary, he was just a bit of a loser really.

  2. One Time says:

    I’ve always thought coffee makes a good first date. It’s easy to escape if things go sideways.

  3. A British Guy says:

    What is it with friend’s and setting you (me) up with someone so ‘off the mark’. One of my best friends did this a few weeks back and, my Lord, how they ever thought I would strike any rapport with this particular girl is beyond me — they obviously don’t know me as well as I thought they did.

    The sentence always begins with, “I want to set you up with someone who I think would be perfect for you”. Alas non. Never again.

  4. Alex Shalman says:

    I think coffee / hot chocolate / drinks / fruit smoothie and walk in the park / or anything else that doesn’t have to last long, but can, is an excellent first date. Obviously no movie, because you don’t get to get to know them, but no dinner either for the reasons you outlined above.

    I want to hear more bad date stories from you, in detail, I find them interesting =)

  5. That Lawyer Dude says:

    Worst date, My best friend set me up with a girl in his bridal party, she backed out last minute but he didn’t tell me, he subbed in a different girl. It was a blind Double date. I am a funny story telling lawyer type who is a foodie, and I like wine and beer (good beer) I had traveled extensively. She was a hairstylist who chewed gum like a cow and was an auto mechanic in her spare time. Though she had a good body I wanted to stick a pick in my ear after 10 minutes. I kept looking at my buddy but it was clear that this was his Fiance’s idea.

    I finished the night and wanted to kill him. A few months later however he scored big. Introduced me to the cutest girl I had ever met. She hated me. Thought I was overbearing over whelming and obnoxious!!!She wouldn’t tell me where she lived (the town) much less her phone number. Of course we got married 2 years later and are together still 25 years later :)

  6. starangel82 says:

    Around here there are no good bars to go to on the first date. They are all loud, noisy, and honkytonk. (That’s small town South for you.) There is a Starbucks and a few mom & pop coffee shops, but every date I’ve recommended these places to claims he doesn’t like coffee. So I’m usually stuck with dinner on the first date. I try to make it during lunch at least. Lunch seems to be an easier first date that dinner for some reason.

    My worst date: I meet a guy for lunch on Saturday. He is still hung over (or maybe started drinking again) from the party he had at his house the night before. He kept talking about the party and how his house was trashed. He answered his cell during the meal and carried on a casual converstation. Then when we were leaving, he tried to pull me into a hug by grabbing my ass. And said, “Oooh, baby. You’ve got a nice ass.” I elbowed away and almost ran for my car. Worst. Date. Ever.

  7. Teifion says:

    @That Lawyer Dude: That’s pretty funny :D

  8. jenmata says:

    I’ve had this happened to me too. I’ve gotten stuck spending more time than I wanted with a guy on a first date. But it can happen because you’ve ordered dinner or, in my case, because I can’t just take one look at the guy and turn on my heels and leave, now can I? I stay for the obligatory drink and chat, while thinking “how am I getting out of this one with out making him feel bad?” Ah dating, if we were paid for enduring it, I’d be rich!

  9. SINgleGIRL says:

    -Teifion,
    You’re right, as a worst date ever it could’ve been a lot worse. I think the reason it stands out in my mind as such was because I felt so much pressure to get along with this guy. I felt like if I said something like, “it’s not funny” my friend would’ve gotten mad at me. And I didn’t want that.
    -One Time
    I wholeheartedly agree. I think coffee makes a great first date.
    -A British Guy
    Our friends mean well. I just don’t think they put much thought into it beyond – I like you/I like her, therefore you will like each other. I’m still open to set ups, but I just know not to expect anything from them.
    -Alex Shalman
    More bad dates stories? Really? OK. I’ll put that on the list. I can think of some funny ones right off the bat.
    -That Lawyer Dude
    Thank you so much for sharing that. I’m smiling right now- with maybe just a little faith in this whole dating nonsense.
    -starangel82
    OK, dear. You win! :-) That just sounds horrible. If I had to choose between lunch and dinner, I’d choose dinner too. But it sucks that those are your only choices.
    -jenmata
    I have another rule about first dates: No matter how bad it is, always stay for at least 20 minutes. I know that might sound cold, but I think 20 minutes is a fair amount of time to spend with someone when I’m completely miserable. I’m always polite about it, always come prepared with a legitimate out. So no turning my heels and leaving after one look, like you said, but no prolonged torture.

  10. Shannia says:

    That’s just hilarious starangel82, I know that at the moment it must’ve been awful, but reading it, i am cracking up!!!lolll
    So not excited to start dating again, i think i just might stay single a little while.. ok my relationship is not dead yet but definately on life support.

  11. iamalejandra says:

    2 things:
    1. I got set up with one of my best friend’s best friend’s best friends (3 degrees of best friendship, lol). Well, ends up that we go out, he invites me to his apartment for a drink and … HE HAD A GIRL SLEEPING IN HIS BEDROOM!! So NOT everytime your friends set you up with their friends you’re going to have good luck!!
    2. I got into plentyoffish after reading your posts about it, and guess what?! Included in my first set of matches was a guy who I already slept with!! HAHAHAHAHAHAHAHAHA (I met him at a party like 5 years ago!!) I laughed so hard my stomach was hurting.

  12. starangel82 says:

    SINgleGIRL – Whoo I win. Do I get a cookie? :)

    Shannia – you’re right. Then it was awful. Looking back on it now, it’s hilarious. If I’m on a bad date or a date that’s not going so great now, I always think ‘At least he’s not the ass grabber.’

  13. SINgleGIRL says:

    -Shannia
    Oh darling, am sorry to hear about the life support. I know it’s a horrible thing to think of right now, but just think, none of these stories are THAT bad.
    -iamalejandra
    The world is too damn small. I’m glad you were able to laugh about it though. I tend to get stomach cramps every time I try a new online dating service and see exes there.
    -starangel82
    You deserve more than a cookie honey (for your willingness to share). And isn’t it great how we can look back at these things and laugh at them in retrospect?

  14. bobbyjensen says:

    Thanks for the story. I agree, and have said for years, online or not, dates are just what they are, dates.