You should try asking this over on May-December Relationships, too - I'm sure they'll have more "been there, done that" advice for you in your situation..
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If you want to have a fling with a younger man thats ok, but NOT your sons friend. You will take a chance of losing your sons respect and he will be very hurt and angry with you. Trust me some how word will get out..
BTW what goes on in your exes house is not your business nor your kids. Your kids are adults and they do not have to visit dad when she is there and they should not be carrying stories back to you. You need to move on..
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My next door neighbor.
Wants to ban all guns.
THEIR HOUSE IS UNARMED.
Out of respect for their opinion I will not protect.
Them with my guns..
The priority here is your son. Do you want to look back and have horrible regrets about a lapse of judgement due to loneliness? You are a parent first, a single woman on the prowl is much lower on the list.