AITA for expecting my ex-roommate to venmo me the $300 we agreed on?
So this is a long one. Bear with me.
Me (25F), my roommate Oliva, and a guy Jesse (23M) all moved into a new place together in July 2025. We'd lived together before so we thought it would work out fine.
Shortly after we moved in, my friend Jacob needed a place to stay. He was only supposed to be there two weeks. Six months later he's still here but it's lowkey fine becase. He pays maybe $300 toward an $800 rent share, usually late, sometimes not at all. He used to sleep on the couch and bring his promoter friends home constantly which drove Jesse insane. Jesse nagged him about it and he mostly stopped. Jacob gives us free coke which is honestly why we don't push him too hard on the rent stuff. Jesse doesn't partake and was always weird about the liability thing since Jacob isn't on the lease.
Also when we first moved in Jesse spotted me $800 for my security deposit. We agreed verbally I'd pay him back by covering his utility share. I've been doing that since October. I think. It's a little complicated because Jacob sometimes contributes and I handle all the bills through autopay and I don't always check the portal super carefully. But I did sit down with Jesse and walk him through it once to show him it was covered. He seemed satisfied.
Jesse clearly hated the living situation and decided to leave. He's also a teacher so he's just kind of uptight in general. He found our friend Ally to take over his spot on the lease. The whole process took about a month and the leasing company was really strict about it. They sent us a scary email about paying on time even though we always pay, just sometimes a few days late.
We worked out the financial transition together. Ally would pay Jesse back his portion of the security deposit directly. Jesse and I agreed explicitly that once Alyssa sent him that money, he would Venmo me $300 out of it to cover his utility share for April and May.
Ally sent him the money. I never received the $300.
I've texted him multiple times. He keeps saying he wants to wait until June 1st to see a full breakdown of everything before he pays anything. He says he wants one complete accounting, not piecemeal payments. I kind of agreed to June 1st in conversation but I feel like the $300 was already a separate explicit agreement we made before that.
He's never acted like this with money before. He always paid rent on time, every single month, never late once. Now he's completely moved out, off the lease, has Ally's deposit money, and I'm having to chase him down.
Is he just being petty because he hated the living situation? AITA for being upset about this?