have you ever been OUT with him...as in out his house in a social atmosphere...is so, is he social with other people or just you? Maybe he has some sort of social disorder that prevents him wanting to go out and sort things out...I'm currently at my mums but I'm only 22 and I also get told I'm smart but I was unemployed for 2 years and didn't really do much. Yay for AvPD (I think it's what I have). (Wiki this if you so wish) I only opened up and "shined" for specific people and never looked for relationships this could happen without him realising
If he doesn't have some sort of disorder then he seems like a waste of space with no ambition.
Memories are nice...but that's all they are...