15 People Share Their Awkward Flirting Stories So You Don't Make Mistakes

List Rules
Vote up the most awkward flirting stories you don't want to repeat.

In an era where dating apps are the most common way of meeting someone, flirting skills have somewhat fallen to the wayside. If you're looking for some tips on what not to do while flirting, check out these awkward flirting stories.


  • 1
    10 VOTES

    They Drunkenly Flirted And Confused 'Tupperware' For 'Lingerie'

    From Redditor u/numanson:

    Me (drunk as hell): "Unlike the other guys, I know when to stop drinking. I know when I had enough."

    She: "Yeah."

    Me: "So, what do you do?"

    She: "I work at Tupperware. I sell Tupperware."

    Me: "Oh, really, so are you wearing it now?"

    She: "What?"

    Me: "Tupperware."

    She: "..."

    I still don't get how I could get so drunk that I mistook Tupperware for lingerie.

  • 2
    6 VOTES

    They Accidentally Convinced Her That They Were Into Her Cousin

    From Redditor u/rjgalloway:

    I once told a girl I liked her brother.

    See, what I meant to say was "I like your bra," but as I was saying that I thought to myself, "Oh, I probably shouldn't say that as it would give away that I've been looking through the folds on the front of her button-up shirt to the bra underneath." So bra and oh got mixed to form bro. And I said, "I like your bro."

    She looked at me funny and said, "I don't have a brother. You must be thinking of my cousin. He's not gay though."

    I walked away, wondering what just happened.

  • 3
    28 VOTES

    They Literally Set Her On Fire, Thinking It Would Be Cute

    From Redditor u/sackup:

    In high school, when I was 14 or 15, I rode the bus with a girl. She was from a different group from me and we did some occasional flirting, but chances for actual interaction were rare. While we were standing around waiting for the buses to arrive one day, I noticed that she was wearing jeans shorts. For some reason, I thought it would be hilarious to light the fringe of her jeans shorts on fire with my lighter (keep in mind... I was guided only by hormones). I thought it would be like a shock-fire or something. Like "woosh!" and then out. So when her back was turned I lit the lighter right under her butt, and of course, immediately the frayed cotton of the shorts went right up and showed no indication of going out.

    Immediately I recognized that I had made a major error and I commenced slapping at her upper thigh/butt area in an attempt to get it out. It did go out, but of course I had run up behind her and apparently begun roughly grabbing at her, from her perspective. Attempting to smooth it over with "I was trying to put out the fire that I had set upon you" didn't go over any better, and needless to say I could have gone to jail. She just decided to avoid me (and rightly so) from then on out.

  • 4
    15 VOTES

    They Thought They Shared A Name And Made Things Weird

    From Redditor u/ieattime20:

    After encouragement, a drunk friend of mine wandered over to a hot chick at a loud party and stumbled into the following exchange:

    "Hey! My name's Luis! What's your name?"

    "Luis??" struggling to hear...

    "Haha! Oh wow! Your name's Luis too! That's so wild!"

    [...]

    "...I'm really drunk." *wanders off*

  • 5
    4 VOTES

    They Fired A Water Toy Into A Girl's Eye... But It Wasn't Full Of Water

    From Redditor u/EsteemedColleague:

    I was at a college party once, and these girls I knew were carrying around these little squirt toys. When the cute one set hers down, I thought I'd flirt a little bit and kind of playfully squirt her with it.

    It shoots DIRECTLY into her eye. The squirt toy was full of VODKA.

  • 6
    4 VOTES

    They Walked Through A Glass Door While Trying To Talk To A girl

    From Redditor u/thcobbs:

    Most awkward thing I've seen a friend do was he was really into this girl, got drunk, went to talk to her at a party at her house...

    Well, he saw her through door and just started talking and walking to her... right through the plate-glass door