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What's the most awkward thing that's happened to you on a date? GuySpeak Group Question!

Unless you're Don Draper or a sensual robot, you've probably had an incredibly awkward moment on a date at some point. Guys, have you ever experienced a really mortifying moment on a first (or 2nd or 3rd) date? How did you recover? Or did you just wallow in your embarrassment? Any tips for smoothing over the weirdness?

Mystery Man says:

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Apart from the usuals - food poisoning, one of us getting incredibly drunk, running into her boyfriend while we were out on a first date (not exactly mortifying, but hugely painful), there is only one.
I dated a trans-woman once without realizing - and before you laugh at me, she was fond of those Mandarin collared silk blouses and I was a lot younger and a lot more innocent.
It was a little awkward when she told me, on our third date but the first serious one, that she was a post op trans. You know, the date when sex is in the air. There was a rather strained silence at the table, to say the least, that seemed to go on forever.
She was looking sadder and sadder by the second, my mind was basically running around like a gerbil on crack, there was that buzzing roar in my ears that you get when you have had a sudden shock and nothing at all was coming out of my mouth.
Picked up my coffee, had a sip, and, in probably the hardest thing I have ever done, said, "OK. Your place or mine?"

The rest is none of your business.

Reformed Player says:

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The only bad incident I ever had was my ex calling me on my second date with my current girlfriend.  This needs a little backstory: about six months before we broke up, we combined cellphone plans.  Then the inevitable happened, and this followed me for months, especially since she was apparently completely incapable of realizing that I didn't enjoy paying for the texts she was sending to her rebound girlfriend.  I finally had enough and threw her off my plan.

So she called to complain that I wasn't paying for her cell phone anymore, and also to complain that I was dating someone else in a roundabout, passive aggressive way.  I handled it by being completely honest.  It wasn't exactly fun to lay out all my previous relationship screwups on the second date, but fortunately, most of them were of the "too nice" variety.

Funny Guy says:

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Not to out do MM, but in 8th grade I once accidentally thumped a girl's head against a tree trunk while trying to kiss her all man-take-charge-of-girl's-face -- like in the movies.

Also, my sister burped in a dude's mouth on her first French Kiss attempt. Poor, Funny Sis.

Girls' BFF says:

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I can honestly say that I've never had a a mortifying moment on a date. I'm not sure how I've managed to pull this off. I'm dumbfounded thinking about it right now. That's not to say that I've never done ridiculous things while with a date but it was usually well within the span of "you know I'm goofy, you've accepted it" timeframe. Like the time I accidentally stepped into a fountain. But the water was SO clear that I couldn't tell that it was water. And it was so still. I stepped right into and right back out and pretended nothing ever happened. Luckily I had on dark jeans so nobody but the 20 or so people immediately in my vicinity saw. They laughed very hard by the way. Almost offensively so.

Chic Geek says:

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Many years ago I had a first date with someone I met on a dating website. First, she gave me the wrong address for the bar. So I showed up and there was a cover, which I didn't expect. I paid, went in, and noticed... a lot of gyrating dudes and loud, thumping music. Yep, it was a gay bar. I left, called the girl, and she was all, "Oh, I meant 2nd Ave not 1st" or whatever.

So I get to the bar where we were supposed to meet and she was there with several friends. Strike two. (She had vetoed my idea of dinner since she thought a bar would be a better way to get to know each other. Clearly she just wanted to bring her friends along to screen me. Or maybe she was an alcoholic.) If you take nothing else from me, learn this: Do not bring friends along on your first date. So we all sit there and drink awkwardly, her friends clearly knowing we're on an online date. At one point, one of her friends turns to us and goes, very loudly, "How is the date going????" Also, it was a crowded bar on a Saturday night.  Strike three. Eventually the friends left and we were on our own. To make a long story short, we ended up going out on a second date which was a lot better. But that first date was ROUGH.

Wise-Ass says:

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This one time I went undercover posing as a post-op tranny to research a story I was writing, and this dude asked me to go home with him! I had to clobber him with my purse.

Gal Pal says:

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Let's just say it was the wrong time of the month to wear a white dress on a date. And let's just say I didn't realize it until hours after the date, when I got home and took off that white dress. Needless to say, I was all by my lonesome at that point.

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10 Comments

chrissie1101

laugh i thought i'd die, Cary, for real. brilliant.

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MM

That made my eyes water a little. Wow. That was incredibly wonderfully caring. Wow.

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I went on a date with a guy who kept talking badly about his sisters. Finally, I asked him what was so wrong with them. He proceeded to tell me about one sister who was a skank and also told me about the surgery she had to have to "remove parts that were damaged from STDs". It was a very graphic description, and probably the most disgusting thing I've ever heard. Date from hell!

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I went on what I thought was supposed to be a movie date....he sat a seat down from me so he "could use both arm rests", and then took off as soon as the movie was done, leaving me waitning for a ride, at night, in a not-so-great are of town.

SimplyLaurel

My boyfriend's car wouldn't start when he picked me up for our first date. He was embarassed, but I thought it was kind of hot that he fixed it in under five minutes. :P

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On my first date with a guy I had been pining for for YEARS, I was a nervous wreck. When he actually finally tried to kiss me goodbye at the door, out of that nervousness I literally laughed in his face! ...um in his mouth...I laughed in his mouth...then I left him standing there as I shut the door in mortification. yeah. poor guy. (fast forward to the future: dated again, never discussed it, married, divorced....what does it all mean??) ;-P

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On the way home from a great date, we hit Bambi. Ka-thump. I screamed like a girl and he said... "well, Bambi's not getting up again", and kept right on driving.

Quiz

Went on a double date/bring your friends first time meetup type thing for an Ok match. He brought his best friend — with whom he had a SERIOUS bromance. My two gal pals that came with later announced (after we'd gone home) that they suspected he was trying to find a coverup for being gay. Haven't heard from the guy in weeks.

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hahha I agree

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