I (21M) have been close friends with “Sophie” (21F) ever since we were 14. About two years ago she moved to another city, but we’ve stayed in touch through FaceTime and texts a couple times a month. Lately though, she’s been taking days to respond to me and doesn’t really reach out on her own. She’s told me she’s been going through a rough time, so I tried not to take it personally. This summer she came by my city for a weekend and texted me asking if I wanted to hang out. I said sure, but when she was here she would either not answer for days or only hit me up last minute, usually late at night when she wanted to meet at some event. On her second-to-last day, I saw that one of our friends had posted pictures of them together at an amusement park, and I kiddingly commented “Oh, so this is why Sophie doesn’t answer”. For context, I’m a pretty jokey person and often clarify to my friends I’m being sarcastic and don’t mean anything ill. Sophie text me later that day saying how that wasn’t cool of me to do and that she had told me the day before that her phone plan was out so there was no reason for me to say that. I apologised and tried to explain that I ment it as a joke. Jump ahead a few weeks and I still feel like somethings off between us so I text her asking how she’s doing and if we’re alright. She says we’re good but “have some things we need to talk about”. She explained that she’s been uncomfortable with some jokes I’ve made. I play flirt with a lot of my friends, both straight guys like me and with my lesbian friends (Sophie’s gay) so I never picked up on the fact it made her uncomfortable. Felt super guilty of course and apologised, explaining that’s it’s no different to me having my straight guy friends call me their “baby daddy” or me calling her “my love” but that I of course wouldn’t do it now knowing it made her feel bad. She asks if I have anything I want to bring up in regards to our friendship and I mention that I think it’s a bit sad she doesn’t reach out that much anymore and when she does it’s to ask for money. Over the past two years I’ve loaned her money whenever she’s asked. It never felt like such a wild thing to me since I have a stable income and she’s been studying. In the last two months she’s loaned around 140$. Now a day later I get a text telling me how it was unfair and insensitive of me to bring up. She said I only mentioned it to have “rebuttal” to her issues with me and that it made her feel terrible, and that she has to pay me back asap and is never gonna ask me for money again cause I’ll just use it “throw in her face” later. All I wanted was to weed out our friendship. I got upset when she called my issues a rebuttal when I was the one that got us to address things from the start. Saying I was throwing it in her face also felt weird since, I simply mentioned it. So AITA for mentioning the money she’s borrowed or is it valid since it’s a part of our current friendship dynamic?