>>48 I understand the monetary and homework worries, and am just curious if you're also reserved because many social activities appear to be or end up being boring. Perhaps the issue is more of needing to find activities that you find enjoyable so that going out isn't a waste of time, even if you don't meet up with someone cool.
>>49 Walking sounds like it may be a good idea to meet people in general,though I'm not so sure it'd work for everyone, since meetings are casual and with diverse people.
Regardless, perhaps you should take such a casual approach to the guy? He said he hasn't dated (and there are billions of possible reasons for this), so suggest that the two of you get to know each other better and try dating because you're attracted to him. (Use the word because.) This is simple and straightforward, and puts him in a position where he realizes that he hasn't really given it a shot, and now there's a good reason to do so. If he says he isn't sure, just ask what harm could be done by trying it out, then suggest a date for not too far off (place, time, etc.).
Will this take guts on your part? Yeah, but not nearly as much as otherwise, since it wouldn't be nearly so bad.
Finally, this approach deals with what may be the cause of his lack of dating and approaching girls: He's perhaps just figured it's less messy to try getting involved with women because he may not end up liking them, and thus is waiting to see that someone actually fits very well with him. Of course, the likelihood of him finding this out without dating is significantly small.