Should I message him first?

Okay so I've known this guy for 3 years, and we're really close as I would imagine. I could go on and on and on about our history, and how great of a guy he is, and some of the messages we send eachother on facebook. We've skyped before, called eachother, we've done just about everything you can do when you live so far away from that person. But Its been a month since we last talked. Hes been having issues with his last girlfriend, and they recently got out of a 1 year relationship. I tried talking to him after that had happened, and we talked like normal. Then a month later, his best friend went and tried to get with his ex, so he was really upset about that. It seemed as if his world was just sort of falling apart. Hes got this girl hes trying to get over, his best friend backstabbing him, and what ever else. He just seems so unhappy. So, I thought I would leave him alone for a while.. Hes always been the one to message me first. When we talk, its endless and our conversations go all over the place. The last time we talked right before he went to sleep he said this; "it makes me happy, i wouldn't have asked to meet anyone else haha, i just feel like, i got lucky" but yeah, anything could of happpened, like, thinking about it now through the past around 3 years i've known you i've had things with other girls and ****, but really you've been around the longest and i just feel really lucky that someone higher than us obviously decided for whatever reason that we need to meet!" Should I message him first? I mean I rarely ever do. I just worry to much, I always feel like im bothering him. What do you guys think?

yeah you should. He needs a friend it sounds like and Im sure it would mean a lot to him if you messaged him for once and showed that you really think a lot of him.

If you're confident in your trust and bond with him, yeah why not? What is the worst that will happen? I'm sure he'll be pretty transparent if he's busy or something. If your bond is close, he should have no problem saying, "I'm busy so we can't talk" Or "Sorry I may not reply as fast" If anything like that was the issue. If not, it'll probably be one of your normal "all over the place" Conversations. Ya just gotta kick start it! :D Good friend, good communication, no worries!

Yeah, you can always send him a message anytime. Just wondering though do you like this guy?