Backstory: When DH (38) and I (36) started dating seven years ago, he introduced me to a close female friend who, upon meeting me, acted fairly uncomfortable. From the looks of things, it seemed that she had been sort of relying on him as her non-romantic "boyfriend" for some time (asking for help with things around her apartment, etc.). There was definitely some sort of tension there as well, and when I asked my now-DH about it, he said that they had never been together, but that he'd heard that she had a crush on him at some point.
I appreciated his honesty and, despite some awkwardness in the coming months (examples: calling him to come over and take care of her when she was sick, despite her roommate being around to help; asking him to zip up the back of her dress at an outing), I trusted that DH wouldn't do anything to hurt me.
DH and I ended up moving overseas and we didn't see this friend for years until she came to town when I was pregnant with DD last year. She was much different this time -- warmer to me, and she was great with my DS. There didn't seem to be any tension between them.
Fast forward to now: DH is on a work trip, and I'd forgotten that she lives in the city he's visiting. He just told me that last night he went to get drinks with her and another mutual (male) friend.
There's one side of me that isn't bothered at all because I trust him and she didn't seem to have that "crush" last time we saw her. But then there's another highly anxious, highly exhausted (because DD is ten months old and not sleeping) side of me that is terrified something happened.
I also don't really like the fact that he told me about it after getting the drinks. Maybe it's that he didn't think anything of it, but at the same time, he knows she used to have a crush on him, so I feel like it would have been more respectful to bring it up.
I'm 90% sure I'm overreacting about this whole thing, but I just wanted to know whether other ladies would feel uncomfortable?
TL:DR - DH went to drinks with an old friend who had once had a crush on him (another male friend was there, too). DH told me about it after the fact, and I don't know if I'm overreacting by feeling worried.