My only problem is that I'm in a challenging marriage of 20+ years.
Should I tell her how I feel to get it off my chest or keep my feelings to myself?
I don't want to make things awkward between us.
-----------------"She's a single mom and I'm a married dad."
Challenging marriage? I am having a challenging time digesting this question.
The answer is NO.
Get out of the marriage then you can serenade anyone you like.
If she is married I would respect her husband and keep it to yourself
Oh please don’t start an affair. Cheating is so so sad. If you are unhappy in your marriage and can’t see it ever getting any better and have fought to save it, then please end it before starting a new relationship. It’s the right thing to do.
I wouldn’t even concern myself with it. She does sound slightly flirtatious but considering that you are married that is not very classy of her.
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