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Answer:
DWEEB
Possible Questions:
Nerd
Geek
Loser
Uncool sort
Dork
Dorky sort
Twerp
Social misfit
Uncool one
Nerdy guy
Hardly Mr. Cool
Geeky sort
Weenie
Nerdy sort
Nerdy type
Uncool person
Nerd's kin
Poindexter
Insignificant sort
Geekazoid
Square sort
Nerdy fellow
Mr. Cool's opposite
Bully's victim
Squarepants
Square peg, socially speaking
One who's definitely not in the in-crowd
One who may be "adorkable"
One in with the out-crowd
Nerdish guy
Nerd's relative
Nerd or nebbish
Live action role player, likely
Insignificant guy (and #7 on the "Top Ten Words That Sound Romantic When Spoken By Barry White")
Brainy misfit