I think it’s fair to pay for dates you plan. Allow him to plan his dates, and communicate about financial boundaries. And for holidays, birthdays, etc, ask him if he would prefer a physical gift or a gift towards his debt.
Buuuttt…if he doesn’t show interest in getting his debt…
I was at a bar in Nashville in 2010 and Kelly Clarkson was there. It was a hole in the wall place. Maybe 20 people in there. She was singing with whoever wanted to sing with her, just hanging out. It was incredible.
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