Simon Seville from Alvin and the Chipmunks.
Oh come on, stop looking at me like that...he's cute, and I mean that more than just physically. I gotta think he'd be fun and easy to talk to, and more than capable of an intellectual conversation when the mood strikes. Even if not 'date', a close relationship would be lovely.
...not good enough? Oh fine then...
Rin from Katawa Shoujo.
I have a thing for artists, I'll admit. I admire them probably more than any other kind of person, and Rin is the embodiment of that. She suffers for her art, tremendously, and struggles to communicate with people because there's a constant disconnect between what she wants to say and the words to say it. She struggles to open up or anything of the sort because she's completely unable to read herself enough to figure out how she feels in the first place.
I sympathize with her deeply, and she has an extremely quirky wit and honesty about her as a result of her issues. She'd be a great person to be around, assuming the enjoyment is mutual.