so I really liked this guy in high school. Both graduated year and a half ago. Since graduation, only briefly spoken to each other but we're still sorta friends. Never completely lost feelings for him. Couldn't ask him out in high school because he had a serious girlfriend. They broke up after high school. He's had a girlfriend since then and they just recently broke up.
I wanna talk to him because he's posting on social media about how upset he is about this recent break up. His ex already has a new boyfriend and she didn't end it well with him.
However, considering we've only spoken briefly here and there since high school, I wanna try talking to him now and at least trying to be his friend. But at the same time, I'm sort going with intentions as more than friends and I'm afraid it may not be a good idea to go in with those intentions if his intentions are to just be friends.

I'm also afraid that by suddenly trying to talk to him when he's vulnerable is also taking advantage of him and his emotions and I don't want to do that because of my intentions are more than friends.
I'm sorry if this is confusing, I just don't know what to do. My mind says no but my heart screams yes and I hate it.

Honestly, I would start out by just being supportive; give him a lot of time to breathe, and just overall be a nice person.
For relationship advice, we'll, ya got me there *shrugs*

I don't exactly need relationship advice. It's just, I don't know if I should try initiating anything because I don't know if he might like me back or just wants to be friends. Because we don't talk much he might not want to talk to me at all about something like this because it's obviously very personal to him

Start off slowly by becoming close friends by comforting him. He will slowly grow attached to you in a more "boyfriend/girlfriend" way. See how it goes from there.

ok thanks. Now to just work up the courage to start the conversation.

Good luck :)

Because he's obviously hurting right now I wouldn't try anything or suggest that you want to be in a relationship, start talking to him though and be a supportive and kind person so he has someone he can talk to. Get to know him better (you might find out you don't like him that much but you'll see), become his friend and wait awhile. I think after a couple of months maybe suggest that you like him and wouldn't mind being with him, if he says yes good on you but if he doesn't just let him know you're still a friend for him to go to. Make sure he's not using you as a rebound though (hence you have to wait to be with him). I'm sure you'll make the right decision :) Good luck bud You have the right idea so just be patient

@parisqueen has the best advice I think. I would add maybe comfort him with the breakup like "That sucks. I'm sorry you're going through that" but also try to take his mind off it by not talking about it too much. Guaranteed he already has people talking to him about it or trying to get him to talk about it. You also don't want to wind up being his "emotional tampon"

Ok thanks guys. I'm going to try messaging him, I just need to figure what to say and work up the nerve to hit send.

Say "Hey, how's it going? It's been a while."

For some reason I always think it's just not that simple

It's so simple :^D You can do it! Just need to figure out what to say after that haha Ask what he's been up to. You can kind of feel out what he's into if he answers with something other than nothing.

In my eyes it's a 50/50 chance. You gotta take the risk sometimes, it worked out for me and my girlfriend till we broke up after a year. (Depressing)

After you hit send everything becomes much easier. You can do it, if you don't nothing is going to happen. I suggest just being honest (not about all your feelings) but keep it simple and sympathetic, example. "Hey, heard you're going through a rough time, just thought I'd let you know I'm here to talk if you need to". You got this bud!