Search Results: flirt with a guy over chat

My friend and I are really close and I think he might like me as more than just friends. He's had a gf for about 16 months. Last summer we began chatting for hours and talking a lot about how he's bored with her but thinks it would break her heart to end things. He told me she was texting some guy in another state in some role playing thing where she was happily married to this guy and had his baby, so maybe she'd be okay with breaking up.

He's told her it was over a couple of times but they made up. He says he doesn't love her or even like having sex with her.
Just lately he's joked that if she died it would solve a lot of problems. He also hates her family, talks about how dumb she is and says he's tired of her. He says he's tired of being unsatisfied and bored.

He's been flirting a lot with me this year so far and talking a lot about sex in general with me, telling me what he does with her and asking me what I've done or might want to do.

I am not trying to break them up even though I think it's dumb to stay in a relationship you don't like. Is he looking for a reaction from me? I tried to give him advice before, which was just be happy with or without her and he's still with her but saying worse stuff by the day.

Why does he keep telling me he wants to break up with her? Should I say anything or just keep quiet?
She's not at our school so I see him more than she does but she is his Homecoming date of course, cause we're just friends. I was asking him about their plans and he said they weren't speaking now and maybe he'd dump her.