Problem is, he's borderline
(Edit: Fine. Said creepy ass shit to me with sexual undertones. Happy?)
The first time, he turned a comment directed at both of us into something suggestive. I believe the comment was "get done". (We're in the South.)
Second time, we were looking at a missing persons poster. I mentioned that she hadn't been missing for long and she was thirty years old, that for all anyone knew she ran away with some other man. Just after that comment, he told me that perhaps she went to Vegas to become a "working girl", because she was enough of a looker to do it. (WTF?!) When I tried to figure out just what he meant, I argued that a stripper made enough money ($90k in the D.C. area, according to my math teacher), and he went on to tell me a story about his cousin, who paid a "working girl" $1k a day for three weeks.
Maybe the fact that I continued the conversation along that vein nullifies his intent, but really I think my intent in responding was to stand up and not be cowed by the line of conversation. And it doesn't bother me that people in general are skeevy, but it worries me that my boyfriend's mom either doesn't know or is in denial of it. I actually tried continuing the conversation with her present by making a remark along those lines. He pretended he didn't hear me. (The fact that he was clearly uncomfortable continuing the conversation in front of her surely is a warning sign.)
I tried talking to his mom about the first incident. He was able to talk himself out of it.
(My boyfriend seems to be neutral - perhaps apathetic, perhaps informedly- about everything.)
Can I let them be married with my conscience clear? I'm assuming that I'll be at the wedding, and the person marrying them will say "Speak now or forever hold your peace".