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Guys, Can a guy with a female best friend be trusted to date?

Anonymous
There's this guy (i knew from high school) that puts in a lot of effort, he's consistent, seems empathetic. He does have some things about him that bother me. For the most part he's ok though.

I know how a lot of guys are that have female best friends. I was a friend to a lot of guys and they found me attractive and some would try to cross the line while others respected me and their relationships if they had one, one even told his girlfriend about me.

Only thing is that his best friend is a girl he fell in love with years ago and I guess he ended up "heartbroken". I don't remember if they dated or not but I really don't know how to feel about this, considering they hang out still, I haven't met her yet but he says he talks/brags about me to her. It's like she's the first person he runs to with good or bad news.

He said she's a lesbian and her and her girlfriend have reached out to him for advice. Why keep her around and still seek out a relationship? I'm going to ask him about her and see his reaction but I want a perspective that won't be altered.
Guys, Can a guy with a female best friend be trusted to date?
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