Ok, this isn't about if it's possible to be friends with the ex, because it is in this case. It's how to deal with her insecure-new-boyfriend. I'll try to keep the background short. We broke up about a year and a half ago after dating a year. Took me about 7 months to get over her. We work great as friends, we just don't have chemistry. So we've been pretty good friends ever since we broke up (there were some shaky times when I was still getting over her but those times are past). So basically, any issues between us have been worked through, and we get along great. I'm not interested in her romantically and have been pursuing other women for about a year now. So she's been serious with this guy for about 6 months or so. He's basically a jock version of myself. Decent guy. I've been around him 4 or 5 times. Non-confrontational, easy going guy. The ex has told me stories of how he has been upset when I'm along for various group activities (I never go out with just them, that would be too strange). He claims we flirt and is bothered if we hang out when he's out of town (he travels a lot with his job). I can't say I blame him for that, it would bug me too, although if this were someone I would potentially be marrying (as I can see them doing), I would find a way to deal with it. It's obvious that he's just insecure about it, nothing would ever happen with us and he knows it. He's just spoiled with women, as he's always gotten what he wants from the sound of it. I don't have too much sympathy for him on this one. She's had talks with him about it before, and in her words "he's ok with it intellectually". Unfortunately she's pretty passive about it and as such we haven't been hanging out as much. This came up when I saw her on Monday, when I found out how much it really bothered him, previously I thought I was just a small nuisance to him. She says she's going to talk with him again about it, because she misses hanging out with me at the coffee shop, talking about whatever and reading books. So I was wondering if I should do anything about it, like, talk to him? Right now I don't think it's a good idea, it could backfire, I don't know how would react. On the other hand, it could reassure him, he doesn't really know me and maybe a chat could calm him down. So I'm wondering what people think. If you have any experience with "the ex's new bf/gf" I'd like to hear what happened. I'm not in a rush to do anything, I'm not in much of a position to do anything anyway, I mean, he either trusts her or he doesn't. But I'd still like to see what people think.