Got a call from HS friend and he wants money...

The problem is not that it would be more logical to get it from his parents, it’s that he tried the exact same story on someone else previously. There is something going on here that is not about dental work.

Do not loan the money, unless you are comfortable with never seeing it again. If you feel you must, then find out the dentist, go to the office and pay the bill there.

Just to clarify… I’m not loaning him any money. The lifespan of my even considering it can be measured in seconds.

That’s really bizarre. As others have said, I’d bet on it being an addiction problem of some kind. It sounds like the sort of story my alcoholic, junkie ex-uncle would come up with.

He was asking his students to pay for his dental work too?

This is what strikes me as odd. He can’t wait a month to get teeth fixed?

Years ago when my wife and I didn’t have dental coverage my wife broke a tooth. It was a few thousand to get it fixed. The doctor put w temp tooth in for her and she had a crowned later when we could swing the bill.

Something tells me your old friend isn’t looking for dental work.

The only people I know that say they’d “appreciate it if I didn’t spread this around to anyone” are getting money for drugs. They don’t want other people to know they’re leeching money off everyone they know.

What I would do is make a few phone calls to dentists and see if any will arrange payments with a small down payment (like a $100 or so). Then, next time you talk with your old friend let him know you worked out an arrangement with a dentist for him and you’d be willing to pay the dentist directly the $100 down payment for the work that needs done. If he really needs work done to get rid of pain (like some seriously impacted teeth) you’ve helped and old pal get moving in the right direction.

Something tells me he won’t take you up on the offer.