Would it be strange to ask an older women out?

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11 Comments

A few years ago I got arrested it was something stupid wrong place at the wrong time type of thing. I had to do some classes because of it I was completely dreading going walking in in a not so great mood.

As the class sat in the waiting room a woman walked in and was cutting through she smiled at everyone and got to me she mouthed “hi!” And gave the cute wave with just the 2 middle fingers lol. I remember thinking wow please be the teacher and sure enough it was.

At the time I was about 23 she must have been about 45-48 she was attractive a little bit aged but a pretty face and a good looking body. Most of the time she wore black tights that I think she thought were yoga pants but they weren’t you could just slightly see her underwear through them.

She didn’t wear thongs always just the booty shorts style ones .. so hot lol. I was mostly quiet all class just sort of sat in the back and listened she always had a thing for me I never got in trouble she would always make eye contact and smile at me during class lol

After every class we had to get something signed and she always found some excuse as to why I had to wait until the end to get mine signed. Once everyone was gone I’d stay and we would talk talk like friends a little flirty we both had the same type of dog I found out she was single always has been had boyfriends here and there

But she was more of the “still young” party type loved music going to concerts and going out with friends which I thought was a huge turn on she was so down to earth and cool.

There was one time we stayed after and we were really talking she had no work out or anything it was just us 2 sitting talking I figured now is the time I’m going to jokingly sort of ask her out if she’s ever around when my phone rang I quickly silenced it as she was talking then it rang again I pulled it out to flip the switch to turn the ringer off and I think she thought I had to go so she got up and starting packing up.

After that I never got a chance to ask her out she missed the last 2 classes and that was it I was pissed but time went on and I forgot about her. The other day I found a paper from the class and it had her name right on it I found her on Facebook she still looks great lol. Does anyone think it would be weird to ask her out? For one she’s almost double my age. We haven’t talked in about 3 years. And other than having a paper from the class I wouldn’t have known her last name. Let me know what you guys think please serious replies thank you.

Ps.... Janice.. if you see this hit me up lol

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75% Normal
Based on 12 votes (9 yes)
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Comments ( 11 )
  • Bazinga
    3 years ago

    Enjoyed your story; Cougars like Janice are the hottest babes out there, and she wanted to fuck you badly. Sorry about the poorly timed phone call. Fate can be cruel, indeed.

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  • clitoriajustice
    3 years ago

    i don't think there's anything wrong with shooting your shot. you should let her know how you found her facebook so it doesn't seem creepy and you shouldn't ask her out in a sexual way, just if she wants to go out sometime. but if she says no you should absolutely respect that!!! if she says no just be polite and then don't message her again.

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    • Anonymous Post Author
      3 years ago

      Would it be weird to message her on Facebook after all this time saying I found an old paper of hers that had her name on it and I looked her up ?

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      • clitoriajustice
        3 years ago

        no i don't think it would be weird as long as you frame it like you want to reconnect because you like her as a person, not just in a sexual way. i think letting her know you found an old paper actually makes it less weird because that's a valid reason to be reminded of someone

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  • dappled
    3 years ago

    I don't see anything abnormal about it, but I do think it's strange that you think Janice might be here when there are about 23 people on the site and 7,793,454,462 people in the world. It's much more likely she's out in the world rather than here, just by the weight of numbers.

    If, by some miracle, she is on the site, I think you might have shot yourself in the foot by publicly calling her "a little bit aged" and saying she doesn't understand clothing.

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    • Anonymous Post Author
      3 years ago

      She has made jokes before about her age or aging but still being cool. As got the clothes I didn’t really say anything bad someone probably should have told her tights aren’t leggings tights are see through when you bend over lol lucky for her she always wore panties not so lucky for me

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  • Boojum
    3 years ago

    A lot of people would find the age difference weird, but striving to conform to culturally accepted norms isn't the route to personal happiness.

    We're all susceptible to projection and we tend to see what we want to see. But if you feel there was some sort of connection between you two, then there's nothing to be lost by you getting in touch with her. Given the time that has passed, she could hardly think that you're stalking her, and there would be nothing creepy about you saying that you recently came across the paper from the class and you were wondering how she's doing.

    However, be aware that it's possible she's forgotten all about you. Students often remember teachers, but teachers can't be expected to remember everybody who's ever sat in front of them, particularly when the class only meets a few times. So I suggest you keep it light, and don't feel hurt if she doesn't immediately recall you. On the other hand, if she does immediately remember you, that could be a very positive sign.

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    • Anonymous Post Author
      3 years ago

      Yea I mean I just thought she was hot I’d be open to just fucking if that’s what she wanted or if she wanted to date I’d be open to that too I do have a big family that is really close I think it would be a little weird bringing her to family gatherings but idc she’s an attractive lady

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  • Tommythecaty
    3 years ago

    If she was that age and still hot you probably don’t have a chance, just a hunch. You should still ask though, I’m always wrong, except for all the times I’m right, which is always.

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  • dirtybirdy
    3 years ago

    Tl,dr. But ya. "Older" broads are where it's at.

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  • Pantyman1001
    2 years ago

    I have a 59 year old roommate that is really a head turner. Her personality is very good and she has a way of making round about remarks about sex. Her boyfriend is impotent and she doesn't ever get the sex or even oral that she desires. I need her

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