I like him :/ I need confidence?

I've liked a guy for nearly a year now, I see him once a week at tutoring. We seem to get on very well, we laugh about and apparently when I get a drink at the tutoring he follows me around . He's in the year above and soon to leave for study leave :/ I've never had the guts to admit I like him.. I'm scared because recently (well yesterday) HE broke up with his girlfriend, and I don't want to make things seem complicated but I might not see him again :/ And I've said I do VIA formspring, but anon so he wouldn't know it was me but I pussied out and said it was my friend on anon but I think he knows but URGH :/ what should I do? I have no confidence,low self esteem and I think I'm not good enough for him or be his type (I'm not slender or pretty) but yeah :/ Help please?