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24 Awkward Ways Women Tried to Hit on Men

17. Thou shalt not steal

Back in college, around 1995 or so, this girl I was in a class with became friendly with me. I wasn’t all that attracted to her, but she was cool and funny.

One day she comes to class and talks about how her stereo’s tape player was broken and she couldn’t play any tapes. I offer to lend her mine. She gets really happy when I tell her. She says that she just needs my tape deck for a couple of nights. Fine, whatever. The next time we have class together, I bring in my tape deck.

She takes my tape deck home and I don’t hear from her for a week or so. Finally I ask about my tape deck in class and she dodges my question. I’m starting to get worried. She’s had my tape deck for a week now and I miss being able to play tapes.

After another week, with her being really friendly to me the whole time, I ask when I’m going to get my tape deck back.

She just smiles coyly. Then she says, “I’m not giving you your tape player back until you ask me out.”

Uhhh. No. I’m not attracted to her; she’s cool, but I’m not interested in going out with her. Plus which, that’s emotional blackmail – knowing that she was capable of that is a huge strike in the minus column. I wouldn’t want to go out with someone so manipulative.

Long story short, she steadfastly held on to my tape deck for months while we became better friends. Soon she introduced me to some of her friends and I hit it off with one of them. I started dating her and it made tape-deck-hostage girl furious. She got really jealous. Eventually she returned my tape deck tearfully. She stopped hanging out with me shortly thereafter, we stopped having classes together, and I gradually stopped dating her friend, too.

18. This isn’t cute, this is illegal

In middle school there was this girl that used to crush on me hard. I had no attraction to her, so it was mostly just her pestering me constantly.

Well one night, while I was out with some friends. She broke into my house and taped over a hundred pictures of her face photoshopped to have her and I together all over my walls. She thought it was the cutest thing in the world, but I hated her after that, and my parents called the cops.

19. “The girl did her homework”

When I was a 24 year old ski instructor, a married sixteen-year old girl told me she wanted to sleep with me. I told her that a) She was married, b) she was underage, and c) the last thing I wanted to do was get a teenage girl pregnant.

She came back a few weeks later with documentation proving she was on the pill, her divorce papers, and photocopied excerpts from a law book clarifying that age of consent laws do not apply when a person is married or has been married.

The girl did her homework.

20. Right over his head

High school. A friend of mine and I used to send notes back and forth as a common occurrence. One day a bit of anatomy showed up in one of the notes in the form of fingers opening a vagina. Asked her what it was about, and she played it off as practicing for art class.

I was not an intuitive lad.

21. Awkward on so many levels

Well it was her grandfather’s funeral, and she very clearly and openly started trying to flirt with me, before they had even lowered him into the ground. Everyone grieves their own way I guess.

22. Not for me, no thank you

I was out with some friends at a bar once, and this older lady in her like late 40’s starts hitting on me, I try to politely decline her advances several times before snapping and saying, “Look you’re the same age as my mother, I’m not interested.” she responds with, “You can call me mama.” Not sure if the vomit was because I drank too much or just general disgust.

23. Kiss ‘n go.

Last day of high school as a senior, I had been involved in the school plays as the dude who changed sets during them.

One of the other stage hands came up to me (I’m 6’4”) and she put her hands on my shoulders (she was pretty short), put her feet on top of my feet, and tried to pull herself up to my face to kiss me. I recoiled, she gave up and left and never spoke to me again.

So that was kind of odd and out of nowhere.

24. Yeah, that’s weird

I was living abroad at China. Was at the club. Really cute girl comes up to me, “Hi, do you speak Chinese?”

My Chinese was terrible but of course I said, “Yes.”

“Okay, cool. I’m Japanese. I think my friend just got drugged and dragged off by some guys. I can’t find her anywhere. Can you describe my friend to the bouncer?”

Fast forward, me talking to the bouncers in super terrible Chinese describing this woman for a solid 20 minutes. Fast forward am like fuck it. Lets just go look for your friend. Can’t friend her in the club. Suggest we look outside

Once, we get out she states, “2 things, 1st your Chinese is terrible. 2nd, That was all a lie. I just wanted to talk to you.”

Probably should have been a red flag there, but dated her for a year and some. Was by far the oddest relationship in my life.