So I really need some advice about something that’s been bothering me lately. My boyfriend and I have been together for a while now, and I really care about him, but there’s this one thing that’s starting to get under my skin. It’s his constant asking for money.

It didn’t start out this way. At first, he’d occasionally ask if I could lend him a bit of money when things were tight, and I didn’t mind. I understand people go through hard times, and I thought I was being supportive. But over the past few months, it’s turned into a regular thing. It’s like, every time something small goes wrong or he needs a little extra for something, he’ll ask me.

It started with small amounts, like $20 or $30, and I didn’t think much of it. But now, it’s more frequent, and the amounts are higher. The other day, he asked if I could help him with $200 for something he said was an emergency. I was a bit shocked, but I didn’t say no right away. I felt guilty and didn’t want to be the “bad” girlfriend, but the more I thought about it, the more uncomfortable I became.

It’s not that I mind helping out sometimes, but it feels like it’s becoming a pattern, and I’m starting to feel like he’s depending on me more than he should. I’ve tried bringing it up a few times, asking if he’s okay or if he has other ways of handling things, but it always feels like I’m met with excuses or him downplaying it. The last time I tried, he said something like, “I’m just going through a rough time; I’ll pay you back soon.” But it’s starting to feel like he says that every time. I’m starting to question whether I’m being taken advantage of, or if I’m just being too sensitive. I want to support him, but I also don’t want to keep bailing him out every time. I’m starting to feel like I’m carrying more of the financial weight, and I’m not sure how much longer I can keep doing it.

I really care about him, and I don’t want this to create tension between us, but I need to figure out what’s going on here. Should I keep helping him out, or do I need to set some boundaries? How do I approach this without making things awkward? I don’t want to lose him, but I also don’t want to be in a situation where I’m constantly being asked for money.