Search Results: bored day or a bad day

He's been with her for over a year and says he's bored, unsatisfied, etc. He keeps saying bad stuff about her and that he's sick of her and wants it to be over. They've broken up before but got back together. I feel like he's trying to get me to tell him to break up with her but I it's none of my business. I do love him but he's with her so he needs to figure that out for himself. I gave him my advice and said if he's not happy he should do what he needs to do to be happy and why act like you're married to someone and can't leave when you're just 18 and are going off to college soon anyway? He said he's going to break it off after graduation if not before and they've already had "the talk" and she's fine with it. It sounds like their relationship is dead or dying but he won't pull the trigger for whatever reason. I think he's maybe not sure if I want to be with him like that and he doesn't want to be alone. Not the best reason to stay in an unsatisfying relationship! He never says anything positive about her and compares me to her, saying how much better I treat him, etc. He often says I sound like his gf and I made his bday by making him his fave cheesecake. He said he was going to tell the gf he was too tired for date night and to not bother coming over to give him bday sex. He's joked about us being a couple and talks about sex stuff with me every day. I know all about what they do. They only see each other once a week for date (hook up) night at his house (he says he's bored with that too) and, of course, she gets to be his date for dances and official stuff. She's not at our school, so I'm basically his school gf but she gets all the benefits, such as they are. But he's said he loves me in some way.

I can't take this much longer. I do love him and would like the chance to see what we could be before we go away to college next year. I'm not trying to marry him or have his babies but I would like to be able to be open about how I feel about him.

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.