/feels/ - Advice & Venting

I’ve been talking to moid for a few months now. Sometimes he tells me about experiences he had with his ex it's not constant, but it happens. I had never seen her and had no idea what she looked like, but recently, while telling a story, he sent me a photo of a famous singer saying she looked like his ex. I think he realized he messed up because he deleted the image quickly, but it deeply upset me.

Yesterday, he told me another story from when he was dating her (it was a toxic relationship; they were constantly breaking up and getting back together). He said he had a close female friend he used to play games and talk with a lot. He claims she wasn't his 'type' and that the friendship only served to fill the void he felt in his relationship, insisting it was strictly platonic. Eventually, his ex found their messages, got jealous, and attacked the girl. However, the girl didn't even know he was in a relationship; she ended up sending screenshots of their conversations to the ex, and the two of them teamed up against him. After that, he blocked the girl and stayed with the ex for a short while longer before they broke up for good.

He says he deeply regrets that relationship, that it was a mistake, and that he only sought out that girl to fill a void. After some time, he and that girl spoke again so he could explain himself, but the friendship didn't go anywhere because he felt she looked down on him and things weren't the same.

He dated this ex 6 years ago, and they broke up about 4 years ago. I’ve never dated anyone before (they dated for years, though as I said, it was toxic and ended a long time ago). I feel stupid because I’ve already told him several times about the things that bother me.