how judgemental is your area? If they see a college aged guy with an older lady, would they give the look?

curious how nice different towns are
In my college days,, I went out with some older ladies. I had to stay in nice areas not to get judged

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DeWayfarer · 61-69, M

Not an issue here. Yet this Southern California. There are whole bars known for "cougars" here.

You don't say anything against them, they won't say anything against you. And that's how it should be.

This nosiness about others private business should be the crime. Instead we glorify being nosy. Yeah I have been in other states were such non sense was an issue.