ADVERTISEMENT

Alright, buckle up! We're diving straight into the absolute wildest, weirdest, and downright cringe first date stories men shared after encounters with women. Spoiler alert: some of these are so bonkers, you'll wonder how they even happened. Ready? Let’s jump right in!

ADVERTISEMENT
#1

The 50 Wildest First Date Disaster Stories from Guys (Yep, It Gets That Crazy)

anon , Igor MashkovPexels Report

So, this guy goes on a first date after kicking out his ex - excited but awkward. After a nice dinner, he casually says he’ll call her again. She shoots back, "Oh, by the way, I got back with my ex today." His response? "Uh, maybe tell me this BEFORE I buy you wine and dinner." Ouch!

Add photo comments
POST
Related:
    #2

    The 50 Wildest First Date Disaster Stories from Guys (Yep, It Gets That Crazy)

    anon , Andrea Piacquadio/Pexels Report

    This guy’s date finds out he’s a Leo and totally loses it. She literally storms out shouting, "What the heck?!" He’s like, “Well, I think I just dodged a super ultimate bullet.” Astrology fail!

    Add photo comments
    POST
    ADVERTISEMENT
    #3

    The 50 Wildest First Date Disaster Stories from Guys (Yep, It Gets That Crazy)

    Megatron4Prez2024 , Katia Damyan/Pexels Report

    This guy’s date brings a friend, fine. But the friend won’t sit at the bar for privacy and expects him to cover drinks and dinner for all. Oh, and she’s there to stop her friend from hooking up with guys! He stared them down, said, "I ain't the one," and bailed - before even ordering a drink.

    Add photo comments
    POST
    #4

    xanax05mg Report

    He picks a pricey spot, and she immediately grills him about his salary, even dropping, "Do you make more than $250k or not?" He’s like, "Wow, no tact here!" He paid the bill, tipped way too much, and bounced. Instant dealbreaker!

    Add photo comments
    POST
    ADVERTISEMENT
    ADVERTISEMENT
    #5

    @Paynen_Sahrow Report

    During the drive to dinner, this guy’s phone vibrates. He checks it - turns out his date accidentally texted him saying, "Oh my God he's so ugly." He pulled over at a gas station, gave her $2 to grab lottery tickets, and then drove off. Talk about a savage exit!

    Add photo comments
    POST
    #6

    The 50 Wildest First Date Disaster Stories from Guys (Yep, It Gets That Crazy)

    Darolotto , MART PRODUCTION/Pexels Report

    This dude arrives to grab a drink and finds his date already blackout drunk. Chatted for 30 minutes, left, and the next day she’s texting him asking why he never showed up. Talk about parallel universes!

    Add photo comments
    POST
    #7

    ksozay Report

    She tells him he’s got 12 months to pop the question. When he *does* propose... it’s to get the bill and dip because he’s got to wash his dog’s hair. Smooth move, but also savage.

    Add photo comments
    POST
    ADVERTISEMENT
    #8

    The 50 Wildest First Date Disaster Stories from Guys (Yep, It Gets That Crazy)

    HugItOutAlready , Pixabay/Pexels Report

    This date went off the rails fast when the woman attacked the waitress for giving her 'side eye.' Yep, she actually got arrested. That’s a first date we’d rather forget!

    Add photo comments
    POST
    #10

    The 50 Wildest First Date Disaster Stories from Guys (Yep, It Gets That Crazy)

    anon , MART PRODUCTION/Pexels Report

    He didn’t even know she had a husband until the guy walked into the movie theater, demanding to know who he was. Nothing like an unexpected chaperone, right?

    Add photo comments
    POST
    #11

    The 50 Wildest First Date Disaster Stories from Guys (Yep, It Gets That Crazy)

    @masaun_k , cottonbro studio/Pexels Report

    When she asked for the priciest drink, the waiter caught the eye of the guy and said everything was out of stock. Brotherly sacrifice lasts forever. Waiter refused tip, but dude tried anyway. Classic.

    Add photo comments
    POST
    #12

    The 50 Wildest First Date Disaster Stories from Guys (Yep, It Gets That Crazy)

    RobWins2022 , Edmond Dantès/Pexels Report

    This guy's date decided to throw a racist fit right in the middle of a mixed race cafe. Not the way to win hearts, obviously.

    Add photo comments
    POST
    ADVERTISEMENT
    #13

    The 50 Wildest First Date Disaster Stories from Guys (Yep, It Gets That Crazy)

    Knautical_J , Brett Jordan/Pexels Report

    She was more interested in her phone than the date, live-tweeting everything from getting ready to the awkward silences. He decided to make the date so weird it’d be hilarious to watch on Twitter. Spoiler: no second date.

    Add photo comments
    POST
    #14

    Sobeksdream Report

    She spent the entire date chatting about her breakup that happened 13 years ago. No topic change allowed. Fun times? Nope.

    Add photo comments
    POST
    #15

    Disastrous-Roll-1599 Report

    He shared his noble goals and instead of support, she launched into a rant comparing Syrian immigrants to rats. He left during her bathroom break. That’s a no from us.

    Add photo comments
    POST
    #16

    The 50 Wildest First Date Disaster Stories from Guys (Yep, It Gets That Crazy)

    anon , cottonbro studio/Pexels Report

    Things were fine until she ranted about his relationship with his mom, called him a "momma's boy," slapped him, and blocked him. He laughs about it now, but wow, that’s some first-date drama!

    Add photo comments
    POST
    ADVERTISEMENT
    #18

    The 50 Wildest First Date Disaster Stories from Guys (Yep, It Gets That Crazy)

    atreides78723 , Tima Miroshnichenko/Pexels Report

    She dropped the surprise pregnancy bomb - and it’s by her roommate/fiance? This one’s a real head-scratcher.

    Add photo comments
    POST
    #19

    The 50 Wildest First Date Disaster Stories from Guys (Yep, It Gets That Crazy)

    chado5727 , king caplis/Pexels Report

    He met a date who used her friend’s photo for her profile. When he called her out, she cried buckets and the dude decided no more online dating for now.

    Add photo comments
    POST
    ADVERTISEMENT
    ADVERTISEMENT
    ADVERTISEMENT
    ADVERTISEMENT
    ADVERTISEMENT
    ADVERTISEMENT
    ADVERTISEMENT
    See also on Rankify.me
    ADVERTISEMENT
    See also on Rankify.me
    ADVERTISEMENT
    See also on Rankify.me
    ADVERTISEMENT
    See also on Rankify.me
    ADVERTISEMENT
    See also on Rankify.me
    ADVERTISEMENT
    See also on Rankify.me
    ADVERTISEMENT
    See also on Rankify.me
    ADVERTISEMENT
    ADVERTISEMENT
    ADVERTISEMENT