Seeing how helpful everyone is on this group I thought I should avail myself of your help.

I haven’t been on the dating scene for a long while, like 10 years(you know… work, issues :))), and I am 35 now. I have a crush on a girl who is a lot younger, 20 – 22 range, and I don’t know what type of things work. I remember when I was younger I use to see girls that were my age going out with older guys and I’m thinking that is my time now? 🙂 We live in the same building, our families know each other, I am quite presentable, good looking above average although I should invest more in clothing as my wardrobe is a bit limited. She is very cute, taller than most girls her age, almost as tall as I am and is very girlie and feminine, which is somewhat rare nowadays. She wears dresses and long hair and has a beautiful overall femininity. How should I go about it?

2 comments
  1. What “works” is very individual. In my opinion – (and Reddit hates this advice) but just be yourself. If you’re unsure if shes dating anyone, ask her – you could be a little funny about it to get a feel for how she feels about older men. “Would you think it was creepy for a man my age to take out a woman your age for a nice dinner date?” Or something similar.
    “Would you ever consider going with me (allowing me to take you) to a …show/movie/the theater/ a hike/dinner … “

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