Brian Krakow

Brian Krakow is the smart kid. Every school has one, the resident school genius and future valedictorian, the only person who seems to do every assignment, even the obvious busy-work ones that don't count towards anything. Brian is currently a sophomore at Liberty High and is already taking calculus and triple minoring. He does lots of extracurriculars: he's the yearbook photographer, he plays flute and sax in he school band, and he tutors Jordan Catalano in English.
He's intelligent and suprisingly perceptive, but even more surprising is his complete ineptness when it comes to relationships in general. But that's typical, isn't it? It seems like the smart kid is never very skilled at social interaction. Brian is a social outcast by his own actions, his shyness and his fear of rejection, as opposed to someone like his friend Rickie who is branded a social outcast by others.
Brian is especially unskilled at dealing with romantic situations, or a lack thereof. He was given the chance to have a romantic relationship with Delia, but his selfish stupidity completely blew that chance. Watching this disaster play out is horribly painful. Unlike Delia who comes to hate Brian because she does not fully understand the situation, the viewer, cognizant of the entire situation, can only pity Brian. Another prime example of Brian's romantic ineptness comes when he and Rayanne are forced to spend the night together after he got them stuck in the school basement (he got distracted looking at Rayanne's legs). Having to remain in close proximity with Rayanne for the night appears to make Brian even more nervous than he usually is around her.
And of course, the main example of Brian's romantic hopelessness: he has an enormous crush on Angela but does nothing about it except show up at her house frequently with a lame excuse. He's entralled with her to the point where he is willing to ghost-write a letter to her. But then, when she finds out that it was him, denies his feelings for her. For his New Year's resolution, he resolved to stop obsessing over her.