Need advice on befriending someone

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Hello. I'm trying to become friends with someone, but I don't know how. Its not physical, I know this guy from online forums, but we haven't really talked as such before this. Both of us are doing similar things, only he's a lot more successful at it, and that is the reason I am interested in becoming friends with him, since both of us are precisely the same age. I could email him and ask for his IM account, but I don't want to look like a crazy stalker or something. I've successfully made friends with others on these forums, but I'm kinda scared to approach this guy. Ok, maybe that's because we're running competing businesses. I feel like I could learn a LOT from this guy, but I don't know how to initialize the friendship. I suck at this, and I really don't want to botch this up. How do I go about becoming friends with him? How do I approach him?

Initiating contact with someone is not my strong point. I know how & what I need to do but also find it difficult. I tend to play out several different scenarios in my head. The best thing to do is be honest about why you are contacting him & what you are hoping to achieve.
Example...I was wondering if I could get your IM if that's ok with you. We have a common iterest and I feel like I could learn a lot from you. Who knows we may be able to bounce ideas off of one another that would benefit us both down the road..
Close with your info and hope that he replies. Hope this helps.

Im in a similar situation.
Out of a lot of people i know on line me and this one guy my age have really hit it off.
But it is something that just unfolded by itself. He is like the one and only person i know
online out of maybe 300 that i would feel 100% comfortable meeting with in real life.
Dont see how a person can make something like that happen.

Not sure what the best way is, but I have a few different approaches. The most common one that I use follows this rough outline:

I tend to start with something they've posted, then briefly describe how I relate to it. After that I usually try to reassure them at every angle so that they don't think I'm a creep or something else I wouldn't want to be thought of as. If they're older than me I can usually skip the reassurances but I somewhat try to prove my worth as a person to respond to or at least consider the message of. Compliments are really useful, as 90% of the time a person will find comfort in having someone say something good about them. I only compliment them if I genuinely mean it though, as fake compliments are essentially lies and aren't a great way to start off a bond.

Bad example: 'Hey, I saw you post this.. blah blah, that's similar to me because blah blah.' 'I'm writing this to you because [insert true reasons here]'. 'I think you seem very nice, and I sincerely mean that.. I'm not a creep.' '[Insert humour/emoticons to induce comfort]'.

There's no real mistake you can make introducing yourself to someone online, unless you aren't being honest. At least that's the way I see it.

I send a lot of random PMs, but there's only really 1-2 people that I've sent more than 1-2 PMs too. Most PMs were for the survey I'm currently collecting results for.

Even if I approach this guy, I find it radioactively difficult to maintain a friendship, and at this point, I am already trying to maintain one. I've never had a friend for more than 6 months, honestly. And when its more than 1 friendship that I have to maintain, the expiry date gets closer. I just don't know what to do, I was going to get socialization training from a friend around a couple months ago, but that friendship ended up in a disaster. I am afraid of having to maintain too many friendships, its a really exhausting task and this situation makes me feel helpless. If only someone could walk me through this, help me through my ups and downs, teach me the ways of this planet, and truly understand me and my situation. I guess that was a description of a romantic relationship? I don't know. But the fact that people consider me annoying, rude, hurtful, and all such negative words, and that all my previous relationships have left me deeply scarred, such that I will never be able to trust anyone again, I find it difficult to find someone who could guide me. I really don't want to go learn how to socialize from a therapist, all those idiots got their heads way far up their you know whats.

Even if I approach this guy, I find it radioactively difficult to maintain a friendship, and at this point, I am already trying to maintain one. I've never had a friend for more than 6 months, honestly. And when its more than 1 friendship that I have to maintain, the expiry date gets closer. I just don't know what to do, I was going to get socialization training from a friend around a couple months ago, but that friendship ended up in a disaster. I am afraid of having to maintain too many friendships, its a really exhausting task and this situation makes me feel helpless. If only someone could walk me through this, help me through my ups and downs, teach me the ways of this planet, and truly understand me and my situation. I guess that was a description of a romantic relationship? I don't know. But the fact that people consider me annoying, rude, hurtful, and all such negative words, and that all my previous relationships have left me deeply scarred, such that I will never be able to trust anyone again, I find it difficult to find someone who could guide me. I really don't want to go learn how to socialize from a therapist, all those idiots got their heads way far up their you know whats.

I wish you the best of luck. I think I've given up on friendship myself, but it'd be nice to hear of a success.

How about posting what you shared with us in your original post with him? Say that you saw him on the forum, think that you can learn a lot from him, and ask him if you could IM some time. Then you can follow up later with specific questions or just to say hi. I would not consider that to be creepy if someone approached me in that matter.

I second the compliment idea! If I'm in a good mood I tend to tell people what I like about them (appearance and attitude) ASAP so that if they think I'm not normal they still enjoy talking to me. When people give me compliments I sometimes can barely breathe because I'm so flattered, I figure it's advantageous for making people like you.
I went years without giving my little sister a single compliment, and ever since I gave honest opinions of what I liked about her, things started getting a little better.
For me the hard part is being brave enough to give the compliment, and figuring out how to say it.

I think I'm gonna chicken out . Also this other friend seems to have lost interest in talking to me. I can forever be a loner, but I can't achieve much success in business that way. I never compliment anyone. But then I barely talk to people to compliment them. How do I get a trustworthy friend? I really need one, and I have no one. I had 3 of those a little more than a year ago, but back then I was obsessing over that stuff, my special interest at that time was being a sociopath and flirting, and I was doing rather good for an Aspie, but I seem to have lost those skills. And I'm too afraid to contact people anymore, and no longer remember how I made those 3 friends in the first place.