Bullish Q&A: Help, My Housemate Owes Me Money and Won’t Talk About It


Hi Jen

I am a 26 year old girl and I live with 2 of my best friends. 98% of the time it’s amazing, I love having them around, the dynamic is so warm and open. We’re a pretty generous household I.e. If you eat some of my pasta I couldn’t really give a fuck. However money has become somewhat of an issue with one of them. We live in a suburb so rent is cheap, bills are cheap and food is relatively inexpensive depending on what you buy. But this guy is always short, I mean he’s owed me money continuously for 3 months now, and I’m pretty sure he owes our other housemate too. It’s as if the generous easy goingness of the house is being taken in relation to rent and bills also. He is very generous with his money when he has it, but it’s getting rarer and rarer as the weeks go on.

I should also mention he is VERY sensitive about money and will go silent if we’re talking about budgeting. He got sulky with me for asking for some money he owes me back last week because he’d made plans to spend his money on other things (including a party and a dinner), as though I was some sort of nagging, boring fun police for asking for my money back. 

My question is how would a bullish woman solve this problem while still maintaining a close friendship with him? 


– Fun Police

Hi there! Yes, you don’t want to nag and shouldn’t have to. Get together with the other roommate and see how much he owes you both. Then take that amount out of your next rent payment (or the rent payment after next, if you want to give him more advance notice). If you normally each pay $550, inform him that since he owes you $70 and your roommate $60, you will be paying $480, she will be paying $490, and he will be paying $680. 

Give him plenty of notice, but make sure you present this as a done deal. It’s not a proposal. There’s nothing to agree to. You and your roommate are going to put the appropriate amount in the pot, and he’s going to make up the rest, and if he doesn’t, the landlord is going to come down on all three of you.

You really can’t be bluffing here. A late fee from your landlord isn’t the worst thing ever, is it? If he doesn’t put in the extra $130, let him know that the late fee is his responsibility as well.

Write it all down. Not like a contract. Just like a normal bill that comes in the mail. Just make a quick document with everybody’s amount for the month (rent split, utilities, etc.), email it around, and post it on the fridge. Cross off each contribution when it’s paid. Do it every month from now on.

As for the rent plan, don’t let him cast this as him paying “extra.” If he objects, say “I spotted you last month and the month before, I can’t spot you again.” 

Don’t let him cast this as you being “mean” or unfriendly. Say, “Our friendship is being damaged by this situation right now, whether you’re aware of it or not. We need to get the money out of the way so we can go back to being normal friends.”

You can’t let these conversations turn into you “nagging” and him resorting to emotional appeals. Don’t ask as though it’s some kind of favor. To the contrary. Bro it out. You say, in a businesslike, slightly-angry voice: “Dude, that is NOT cool to be spending money in front of me without paying me back. It’s super-rude. It’s not cool. You are damaging our friendship by doing that.”

And next time he asks you to spot him some cash, laugh and say, “No, haha. You saw what that did to our peaceful housemate relations last time. Never again!” (haha joking NOT JOKING)

You said you want to remain close friends with him, but I’m not sure he wants to remain close friends with you. It seems that he benefits more from exploiting your friendship. Keep that in mind. 

As much as you want to be friends, you’ve entered a business relationship with this person, like it or not. Now, you’ve got to get the business done before you can think about resuming normal friendly relations.

Good luck.



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