Funniest (looking back) date?

What's the funniest or weirdest date you ever went on? (true stories only!) Maybe wasn't funny at the time, but looking back it's hilarious? Lots of detail please! :D thanks. Funniest gets best answer!


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Most Helpful Guy

  • This started out badly. it was a double date and my friend had set it up, but it turned out my date was the sister of a friend of mine I handn't seen in a couple of years. She had been the kid sister and we handn't been really friendly back then, and since her brother had told her so much about me it was awkward right from the start.

    Then she broke the heel of her shoe on a storm drain grating and wound up going to a concert wearing a pair of old tennis shoes, much too big, that my friend had in his car. She looked pretty funny shuffling around like a clown in the huge old shoes.

    It had been raining and in the parking lot on the way back from the show she slipped in those shoies and banged her tail bone. By the time we got to the cafe she could barely get out of the car, and I had to almost carry her into the cafe.

    Then, since she couldn't move sideways, she banged into a waiter and he spilled a couple of beers, mostly on her.By that time she was really mad, in pain, limping, with wet tennis shoes and smelling of beer.

    My friend was really distraught over this situation, and blamed himself for setting me up with her, but there was nothing good happening anyway and I wasn't really upset. In fact I had to suppress laughing and she knew it, which just made her madder.

    When we dropped her off, clumping up the steps in the tennis shoes with me supporting her, she had cooled off and was even laughing herself a little. But she turned aside when I tried to kiss her. At least she could have thanked me for all the work in carrying her around!

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    • Clearly the funniest, no?

    • ROFL yess....that must've been HORRIBLE!!!!!

      best answer to you :D

    • Haha I would have laughed at myself right from the start! I had to wear my guy friends size 15 shoes to sneak out on a school china trip and I was running around outside with my friend jumping barriers running across busy roads and everything it was just funny I fell down heaps and got wet cause it was raining but I didn't care.

What Guys Said 0

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What Girls Said 1

  • LOL! I was fresh into the dating world, late teens. He was 20 and looked pretty hot; so I said yes when he asked me out on a date.

    We met at the restaurant, but when the waitress came, he said he wasn't going to order because he didn't have any money! So, of course I felt bad, so I got his food for him.

    Then when we left, I asked where he was parked, and he said he didn't have a car; that he'd walked! Yes, it gets worse lol.

    He then asked if I would give him a ride to his friends' house; apparently, he was HOMELESS and hadn't told his friend he wanted to crash there. So we get there, no ones home, and the door is locked.

    Of COURSE it would be! lol

    He wanted to go home with me (I lived with my parents still, I was in high school!); I told him absolutely no (thank GOD for still living with the rents! lol). I let him use my cell to make a few calls to find somewhere to go, but no one answered. Thankfully, I had the best excuse in the world to get the hell outta dodge.I didn't want to get in past my curfew!

    Lol man that was a rough night! Thanks for the reminder, though; and the laughs!

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