“Jaw With John” – Older Man Runs Into Age Difference

*Author’s Note: I really found the header image too funny not to use.*

I’m a 61-year-old guy. I’m not married and I have no children. I regularly run into this cute girl (who is about 25) at a park where we both work out. We make passing comments to each other. Most of the time she is friendly toward me. I would like to ask her out. Do you think our age difference is too great or would it be OK to ask her out? I am in good shape because I work out most days, so I look about 10 years younger than I am. — Older but Young in Charlotte

Dear Older:

Here’s the thing: you need to build up a rapport with her before you ask her out. Don’t be that creepy old guy who hits on younger women randomly. Talk to her first. Maybe run with her and then you can casually see if she’s interested in you/available/wants to go out with a much much much much older man.

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