Question:

 
This isn’t about sex or men; it’s about money (you’ll probably say all three go together anyway). But maybe you can offer your advice.
 
I was shopping with a guy I’m dating and when he went to pay with a credit card the manager made a big deal about having to get approval, so I loaned my friend $75 to pay for the purchase.
 
Afterward he said I should remind him how much he owes me. I felt since I loaned the money to him, he should note it and pay it back.
 
Well, it’s been about a month and still no word. I did not say when to pay back the loan. On the one hand I think he should take responsibility to remember and return the money. On the other, I should probably just pick up the phone and call him and say when he gets the money to send it to me (and give the address).
 
He lost his job about two weeks ago and I’m sure he’ll have other bills to pay. Would you let this slide or make a subtle call and gently remind him he owes the money?
 

Answer

Your situation reminds me of a friend hinting at me to lend him money. “I only have $3 to my name,” he said. “What should I do?” Here’s what I told him: “Change your name.”

Of course, it’s too late to tell your friend to change his name but it isn’t too late to tell him to change his tune. You’ve got two parallel goals here—to get your $75 back and to maintain the friendship. It has to be said that his request to have YOU remind HIM to pay the money foreshadowed this situation. That’s like saying, “remind me to say thank you” to the very person who did you the favor. WTF? That should have told you right there that the money was going to be next to impossible to get back. Or that it’s going to take great effort.

Your best bet is to text him something like, “Hey, I just got my credit card bill and your $75 charge came up. How do you want to handle it?”

His response will say everything you need to know. Is he belligerent? (“Dude, I can’t believe you’d bring something like that up when you know I just lost my job!”)

Is he passive aggressive? (“Oh, great now even my friends are turning into bill collectors!”)

Or is he being straight up? (“Hey, I absolutely intend to pay you back but can you give me some time to get a job first? I’d really appreciate that”).

I expect him to do the wrong thing because he started off on the wrong foot (the borrower should NEVER ask the lender to remind him of the debt). If you want to preserve the friendship turn the “lend” into a gift. Tell him you know he’s in a bit of a pickle and that you’re gifting him the $75.

And from here on out the only thing I’d ever lend him is your ear. But even that you probably won’t get back.