So I (27F) have this friend, let's call her Lila. We've been friends since college, and she’s always been the “free spirit” type — changes jobs a lot, always got some big idea going, etc. Last year she asked me if she could borrow $400 to “hold her over” until her next freelance check came through. I hesitated but ended up sending it to her cause she said it was urgent.

Anyway... that money never came back. Every time I brought it up, she’d be like “ugh I know, things are tight, but I haven’t forgotten, I swear.” That was like 10 months ago.

Last week she texted me out of nowhere asking if I could lend her another $300 — this time for rent cause she’s “in a bind.” I straight up told her no. I said I can’t keep giving out money when I haven’t even seen the first loan back. She got all weird, saying I was being cold and that “real friends help each other out.” She even dropped the classic “it must be nice to have money to sit on” line.

I don’t even make that much, I just budget well and try not to put myself in dumb situations. My boyfriend says I did the right thing and that she’s taking advantage, but I still feel guilty for not helping her out this time, especially cause she sounded really stressed.

So… AITA?