How the hell do I approach a guy who is never alone?

I feel stupid for posting this, but there's this guy at my school that I find extremely interesting and that I'd really like to get to know. I wouldn't mind to sneakily approach him and start a conversation, but the dude is NEVER by himself. Everytime I see him, he is either sorrounded by 3-7 noisy friends or he's already talking to someone else. He even takes my bus once in a blue moon, but even then, he's always with a friend. I'm acquainted with some of his friends/classmates and am on good terms with a few people who know him, but I wouldn't exactly call those folks "friends" and I'm not anywhere near enough comfortable with them to simply ask for an introduction (that would be awkward, believe me). Furthermore, he skips school nearly every other day so my odds get even smaller. I live in a small city, so you bet you will see someone you know when you're out on Friday and he does go out a lot, but I have yet to see him anywhere (though I don't go out that much anyway). What am I suppose to do? Should I start drinking my face off every Friday and hope I will see him? Or should I just start approaching his friends, so they can introduce me to his other friends and then they can introduce me to him? That's so much work!

Anyway, he is just really sociable and probably isn't aware of how unapproachable he is. I also doubt he is avoiding me since he barely even knows who I am. It's just really frustrating because it's so rare for me to find guys I'm interested in. I have no problem chatting him up, but with his friends there, that is five more people I need to impress and the setting would be just awkward since none of them know me. The only time I see him being alone is when he's walking home or from class, but he walks so damn fast and I have no intention of racing after him in case he's in a hurry. Everything that I can think of at this point just seems awkward and forced. Should I just give up?

This is quite the interesting forum I've come across. I'm still wondering why there has to be a whole website dedicated to love advice from strangers, but I digress.

Here's the one thing you need to know when it comes to dealing with these types of situations: the man seems to be the type that is one and inseparable with his friends (duh). My suggestion would be to tag along with his clique, and become well acquainted with them. This is fine as long as the group isn't filled with a bunch of assholes. I can say this for myself since I'm part of a large group of friends. We didn't mind at all when one of our buddies brought in a girl to join our band of meme obsessed losers. You need to be able to establish in his eyes, the fact that you exist. Otherwise getting alone and intimate with him isn't going to work, since he doesn't know you. I mean, I barely get alone and intimate with strangers (Surprise right?) so I can say this from experience.

You also need to make sure that he's comfortable around you, but not too comfortable so that he starts seeing you as a friend for lyf. This can typically be accomplished by merely being in his presence, and him noticing said presence through consistent (yet not creepily frequent) communication with him and his friends. It's a psychological effect where the more familiar something is, the more comfortable one becomes with it. The more comfortable he is with you, the more comfortable he'll feel being alone with you, thus pushing you closer to your goal.

Lastly, when you've already established a relationship with him (the non-romantic kind) you have to make sure that you get your intentions across in the span of 6 weeks (ie. telling him how you really feel). That's just some statistics I found online in E-harmony. I don't know why I went to THAT length, but there you go.

Look, I know you don't want to get too worked up trying to work yourself into a group just for one guy, but that's just my fortake on the subject. Feel free to disregard some of the advice I gave.

People who are sociable and have many friends may not be that perfect as you see. Sometimes they are empty of feelings and not so many deep friends indeed. Therefore there is chance for u to be his deep fd if u can listen to him, wait for him or support him when he got frustrated. Being with that man is not a easy task for you with your patience, initiative and perseverance, but better leave and find another if you are sure of not worth to do it.