Well if 80 year old man asks 18 year old out it might be slightly funny although it's more disturbing than funny. In your case you are 28 though. So I am not sure what would be so funny if you ask women out, younger or older, no matter. Not sure what's funny or unusual about it.

As about high school, high school was over 10 years ago for you . You are out of high school.

Come think of it I was asked out once by a 70 year old when I was maybe 35 the most. I politely declined as I was not interested but it never occurred to me to laugh

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