Anonymous wrote:Ugh OP, this is absolutely an issue! It's not $100...1k is a lot! It really says more about the people who take advantage of his generosity.
Be the bad cop. Tell him to send an email to the group that owes with a deadline of Friday transfer to his Venmo or whatever. I'd leave it at that, If it makes him uncomfortable, tell him to blame you, Wife insists on repay, junior needs braces soon. Or he expenses it through his company, if this is a work related tab.
My DS 16 is your husband in the making. I have had battles with him since ES trying to teach him that while it's fine to front 10 bucks here and there, kids take advantage of his generosity.
I agree with this- people need reminders and a deadline should get results! If he doesn’t like doing that, he needs to stop putting himself in this situation