Need Some Personal Advice/Help

[Jackabomb]

My family just PCS'd from Korea to Carlisle, PA. My best friend moved also. They went to North Carolina. We keep in contact through skype. He and his girlfriend have been doing long-distance since July. They've been dating since about April/May of 2012. His plan was to return as soon as possible so they could get married.
A few weeks ago he talked about being worried about the future.
Last week he mentioned having family problems, fear of the future, and worrying that his girlfriend would break up with him. He pointed out that she had done so once before. This is true. They broke up some time in the winter and got back together some number of months later. I don't remember how long they were apart because I wasn't very close to the issue. This will make more sense shortly.
On Sunday she did break up with him. I don't know why. I didn't really know her very well at all. She was my best friend's girlfriend. Although I saw her frequently and I was grateful for the happiness she gave him, we had little in common. We rarely spoke since our only link was through this guy, of whom we both saw different sides. I knew him as a friend. She knew him as a potential future husband. When we did speak, it was usually about school as we had taken similar classes the previous year. Normally we would only talk if we had all been hanging out together and then he had to leave for a while. I doubt she has any opinion at all of me. If she does, it probably mirrors my own: watchful caution. I never really trusted her very much and I don't just say this after the fact. I was often uneasy around her and wondered if maybe they weren't moving too fast. I won't tell him this now because it wouldn't serve any useful purpose other than to make me sound stuck-up and conceited. I never told him before because a. I didn't know her and b. what did I know anyway?
See, I've never had a girlfriend. I've never even asked someone out. So I have no idea what a breakup is like. And I don't know how heartbreak feels, especially with a relationship that far progressed.
He's my best friend. I want to do whatever I can for him. I want to help him or do something. Anything really. I have no idea. I would appreciate some help from anyone who's been there before. Either from my side or his side of things. Anything would be helpful.

Thanks

[Scotty]

Here should be some required reading for him (and you, and everyone for that matter):

!@#$ yes or no (laced with profanity)
6 Toxic Relationship Habits Most People Think Are Normal (probably also riddled with expletives)

That should get anyone interested to go read more of his stuff, and hopefully in the case of your friend, shed some light on what went wrong.  I'm confident a good part of the above applies to him.

I recently split from what I would consider my most unhealthy relationship I've ever been in, of which we violated every one of the above mentioned 6 toxic habits.  My recovery method?  Get out and meet new people, both male, and especially female.  It's not difficult to do, and my "recovery" ended when I was driving home with women's numbers in my phone.  Less than a month, and I couldn't have been happier.  For that, go watch:

How to Hold Conversation Like a Man
The Piano Speech

And blam!!! He'll wonder why he ever tolerated the old relationship from day one!

[Jackabomb]

Thanks for the response, Scotty. I didn't watch the videos because it's late and while I might burn 45 minutes online, 59 minutes on a video is just irresponsible. I read the articles, though. Good advice for the future and I'll probably send it along to him. Not yet though. I'm not sure he'd take it well at this stage. I'm concerned that if I say the wrong thing at the wrong time I'll make him feel even worse than he does.

[DarkTrinity]

Well the 6 Toxic Relationship Habits Most People Think Are Normal article was actually quite interesting (and funny). In the early stages on my relationship we were both guilty of doing a few of those. #1 was a problem for a while until one day we both just agreed that the past is the past and it's just holding us back and the future is the important thing.

As far as your friend goes, honestly I don't think a year and a half is that long of a time, not even to be getting married. I've been with my boyfriend for 7 years now and I'm still not married. Heck, with some of the people I know, they're no motivation for me to jump into marriage. Also, I have yet to see a long distance relationship work out in the end. Maybe there's someone somewhere, but humans need physical interaction, especially with their significant other.
And for trying to help him, there's really nothing that will make him feel better right now. All I can really suggest is that you just be there for him and try to make him laugh as much as possible. I don't know if men like to talk about their break ups as much as females... but hey if that's the case, just listening helps.