Yes, at the beginning it is always the hardest.  I know that in school or in clubs, there are always opportunities to pair up or to work in a group.  Don't be obvious, but go out of your way to be put in some situation where you guys would have to talk or interact.  Even sitting next to him could be the key... you could first start doing your work together, or helping each other out.  If you are yourself, and nice, he'll like talking to you and things will start to flow.  After you've had these first interactions and started to become friends, you could then more easily invite him to go do something with you and a couple friends or something over the weekend.  Then, if you seem to really be getting along, hopefully doing something alone will happen along the road.  I know it's a process, but you can do it.  Just try sitting next to him as a first step and getting in some talking.  Ask him questions or anything.