Geez, she just too nice to people! I know Ilana is a positive and good-nature person. And I know Ilana isn't Kimmie gorgeous but she pretty and can do much better. I imagine that little nerd is giving his right-hand a workout that it haven't seen in years!
I wouldn't say he's a nerd as much as he seems like the lovable bumbling guy that actors like Michael Cera and Jesse Eisenberg tend to portray.
The writers of this show are intentionally pairing up unlikely characters rather than following the status quo. This may seem unrealistic but there's a big world outside of the stereotypes you see in high school.