First of all its not the woman I'm worried about, she's attractive but seems trustworthy. It's his behaviour that bugs me. He works with this woman, she had a bad bust up with her boyfriend about 9 months ago. During this time to make her feel better, my boyfriend has invited her to his family dinner and a pool party we were both going to. He has made comments just observing that she had bigger boobs in a certain picture and how toned she's recently getting. Or if she mentions a cocktail at a bar or film she's seen, he has to try it too They text each other quite often about non work related things, not flirty exactly but sometimes he puts up indirectly sexual memes. I recently got angry about the behaviour and now he dosent mention her, but last week he was drinking after I went to bed and he was texting her, apparently they have a drunk text pact, which he wouldn't explain. Still nothing too flirty, but he joked about her being a lesbian and asked her if she liked her woman like her glasses... Sat on her face. I meme I sent him days agoI. I just find this inappropriate or am I being crazy?