Anime where a person in love is emotionally bankrupt, so their crush comes off as creepy.

Akito from Kodomo no Omocha (haha, you can't pick it now, Lai-Lai).

You can't tell when he's sad, angry, happy, or anything. He talks in a monotone voice, like that principal from Ferris Bueller's Day Off.

He has a crush on Sana, but is so bad at expressing his feelings, that even after he steals a kiss, she just thinks he's being a jerk.