I'm talking to a guy who I know finds me attractive, so this isn't about me thinking he's not interested in me. However, there have been several instances where the things he says about other women have made me feel uncomfortable, and I'm trying to understand how men see this kind of behaviour.
For context, he's told me he's slept with around 50 women, and he can go into quite a lot of detail when talking about women's appearances and his sexual experiences.
For example, I once asked him when he last dated someone, and he told me about a girl he went on a date with who apparently looked like a model. He went into detail about how everyone in the restaurant stared at her and how she had "the most perfect nose I've ever seen". I remember feeling insecure listening to this, but I also wondered why he felt the need to give me that much detail about how she looked.
Another time, I told him I was going to get laser hair removal. He asked where I was getting it done, and I said everywhere. He responded by saying, "Good, because once I went down on a woman and her stubble down there was unpleasant."
I found that quite strange. I was just talking about getting laser, and suddenly he was telling me about a sexual experience with another woman and what he disliked about her body.
The most recent incident involved my older sister. He asked to see pictures of her "out of curiosity", and when I showed him, he kept saying how gorgeous she was, repeating it around four or five times. He pointed out that my younger sister and I look different from her.
He then said my sister's fiancé was "punching", meaning he'd done well for himself because she's attractive. I said her fiance was her exact type as she likes bald men and he joked that he should then "shave his head before he drives down to where I live". I found that particularly disrespectful given that he's talking to me romantically. When I challenged him, he said he was joking, and he's since apologised.
There have been other comments involving women, too, so it's not just one isolated incident. His instagram following also makes me uncomfortable as he follows over 1000 women. I want to emphasise that I do think he finds me attractive as well. I'm not saying he doesn't desire me. It's more that sometimes the level of detail he goes into about other women's appearances and his sexual experiences makes me feel like I'm one of his boys.
Please can I have some insight?