My roommate has been late paying the bills. We’re good friends, but how can I approach him about the situation?

Dear Dave,

I have a roommate, and we’ve shared the same two-bedroom apartment for about three years. During that time, we’ve always had an agreement that we would split the bills fifty-fifty. But for the last several months, he’s been very late paying his half of the bills. There have even been a few times when he didn’t pay his part at all, and I had to cover the entire bill. We both work good jobs, so money isn’t an issue. He says he’s broke, but when I ask him where all his money goes, he just shrugs and acts like he doesn’t know. We’re good friends, so I don’t want to be cruel. How can I approach him about the situation?

Mikhail

Dear Mikhail,

No matter whether you’re talking about friendships or business dealings, to be unclear is to be unkind. Believe me, I understand you don’t want to be mean to a friend. But situations like this should always be addressed directly and quickly, before things get out of hand.

You said you were good friends, and not just roommates, right? My advice is to suggest a night where you both just hang out at the apartment. Offer to pay for dinner to be delivered, and just relax and watch a movie or a game together. Before the night’s over, tell him there’s something you’ve been wanting to talk to him about, and begin an understanding—but firm—conversation-about the last few months and the situation with the bills. Let him know he’s a good friend, and you enjoy his company, but the roommate agreement isn’t working out because he’s not living up to his agreement to pay half the bills. Give him every chance to give a reasonable explanation for things, but make sure he understands that you two aren’t going to be able to be roommates much longer unless he starts paying on time.

Being understanding is key in a situation like this, Mikhail. You don’t want to approach him with a bunch of accusations, but at the same time, you need to know what’s going on. Maybe he needs help learning to budget money properly. You said both of you have good jobs, so that means his money has to be going somewhere. The problem is it sounds like it’s not going to the right places.

When a friend is having a rough time, you should always do what you reasonably can do to help. But in this case, he’s got obligations he needs—and agreed—to live up to. Do what you can, but in the end, he should understand it’s time for him to get his act together.

—Dave