Possible Questions:
- Jerk
- Dolt
- Square
- Doofus
- Oaf
- Dweeb
- Bore
- Geek
- Loser
- Square one
- Uncool sort
- Dork
- Dorky sort
- Twerp
- Social misfit
- Lunkhead
- Schlemiel
- Goofball
- Uncool one
- Schmo
- Wimp
- Bookworm
- Egghead
- Social outcast
- Hardly Mr. Cool
- Wimp's cousin
- Geeky sort
- Wonk
- Weenie
- Uncool fellow
- Twerp's cousin
- Antisocial sort
- Unlikely prom king
- Square, updated
- Eggheady sort
- Uncool person
- Uncool collegian
- Bookish one
- Uncool type
- Uncool dude
- Square figure
- Socially inept sort
- Overly bookish sort
- Oafish one
- Geeky type
- Geeky sort found within this puzzle's four longest answers
- Geeky one
- Computer geek
- Taped-eyeglasses wearer
- Socially challenged person
- Poindexter
- Geeky guy
- Drip
- Computer geek, e.g.
- Bully's prey, traditionally
- Unlikely party animal
- Unlikely class president
- Square figure?
- Scholastic stereotype
- Pocket-protector wearer, stereotypically
- Overly bookish type, stereotypically
- Mathlete, stereotypically
- Jock's antithesis
- Inept individual
- High school bookworm, stereotypically
- Dweeby sort
- Dull one
- Bully's target
- Whom a bully may bully
- Unlikely prom king candidate
- Unlikely candidate for prom king
- Unhip type
- Teen comedy stereotype
- Techie, traditionally
- Stereotypical sci-fi fan
- Pocket protector wearer, in stereotypes
- Mr. Uncool
- High school outcast
- Geekazoid
- Eggheady sort, stereotypically
- Dweeby type
- Dweeb's cousin
- Computer ___
- Computer __
- Brainy, socially inept sort
- Bookworm, in stereotypes
- Bookish type
- "Happy Days" put-down
- Unpopular sort
- Unhip sort
- Unhip person
- Uncool fellow, stereotypically
- Uncool character
- Trekkie, to some
- Taped eyeglasses wearer
- Steve Urkel, for one
- Stereotypically uncool collegian
- Stereotypical techie
- Stereotypical computer programmer
- Square type
- Square sort
- Society oddball
- Socially inept type
- Socially awkward type
- Social lightweight
- Social dud, stereotypically
- Sci-fi conventiongoer, stereotypically
- Role in many teen flicks
- Pocket-protector sporter, stereotypically
- Pocket-protected one of stereotypes
- Pocket protector wearer, perhaps
- One who's not in
- One who ruins the curve, stereotypically
- One lacking social graces
- Obsessive type
- Modern misfit
- IT guy, stereotypically
- Inept individual, stereotypically
- Ineffectual person
- In-group outcast
- In-crowd outcast
- High school misfit
- Hardly one of the in crowd
- Hardly a hipster
- Guy with little chance at a supermodel, stereotypically
- Future CEO
- Dweeb's pal
- Dweeb's kin
- Computer geek, for instance
- Bully's target, often
- Bully's target, maybe
- Bully's prey, perhaps
- Bookish sort
- "Kick me" sign wearer, stereotypically
- Wonk, maybe
- Urkel of Family Matters for one
- Unpopular student
- Unlikely homecoming king
- Unlikely escort for a prom queen
- Unlikely clique member
- Unhip one
- Uncool student
- Uncool kid
- Uncool bookworm
- Typical Rick Moranis film role
- Twerp's next of kin
- Twerp or jerk
- Totally unhip type
- This may be hard to date
- Teen-movie persona
- Teen outcast
- Teen movie stereotype
- Techie, often
- Techie, maybe
- Target of taunts
- Swot : Britain :: ___ : America
- Swot
- Swirlie victim, perhaps
- Studious sort, and proud of it
- Steve Urkel on "Family Matters," e.g.
- Stereotypical sporter of a pocket protector
- Stereotypical science student
- Stereotypical pocket-protector wearer
- Stereotypical Mensan
- Stereotypical computer hacker
- Square of a sort
- Square hidden in each of the five long across answers
- Societal klutz
- Socially ineffectual person
- Social washout
- Social outcast, maybe
- Social oddball
- Social greenhorn
- Social bungler
- Slashdot reader, maybe
- Single-minded sort
- Single-minded person
- Simp of a sort
- Screech or Urkel
- Scholastic sort, perhaps
- Role-playing game player, stereotypically
- Rick Moranis in "Ghostbusters," e.g.
- Revenge-seeker of film
- Quiz bowl lover, say
- Propeller-head
- President of the Chess Club, to some
- Poindexter type
- Pocket-protector sporter
- Pocket protector purchaser
- Pi Day celebrant, perhaps
- Pharrell Williams's rap group
- Person who may be "adorkable"
- Person who gets picked on
- Overly techie type
- Overly brainy sort
- Overly bookish sort, stereotypically
- Overly academic type
- One with no hope in a popularity contest
- One whoÂ’s unhip
- One who's socially clueless
- One who's socially challenged
- One who might snort when he laughs
- One who might celebrate Towel Day
- One who might celebrate Pi Day
- One socially challenged
- One needing social work?
- Oddball of a sort
- No sophisticate he
- No jock
- Napoleon Dynamite, for one
- Napoleon Dynamite, e.g.
- Modern square
- Mathlete, perhaps
- Many a Pi Day celebrant
- Many a character on "The Big Bang Theory"
- Lover of brain games
- Lout: Slang
- Jock's counterpart
- Internet addict, perhaps
- Intellectual sort
- In-crowd outsider
- High-school put-down
- High school bookworm, in stereotypes
- Hardly The Fonz
- Hardly a BMOC
- Guy with his nose always stuck in a book
- Grade school designation
- Geek's cousin
- Filmdom's Napoleon Dynamite, for one
- Feckless fellow
- Excessive studier
- Encyclopedia reader from A to Z, say
- Eggheady sort, in stereotypes
- Dweebish sort
- Dullard, in spades
- Dull guy
- Drip's cousin
- Dotcom millionaire, stereotypically
- Doofus-y sort
- Disappointing date, maybe
- Dilbert, e.g.
- Dateless sort
- Cross ___ (shameless!)
- Creature in Dr. Seuss's "If I Ran the Zoo"
- Contemporary dull one
- Common teen-movie persona
- Common butt of jokes
- Clodhopper's cousin
- Campus outcast
- Campus misfit
- BullyÂ’s frequent target
- Bully's victim, often
- Bully's target, perhaps
- Bully's prey, often
- Bully's prey, in stereotypes
- Brainy person, and proud of it
- Brainiac's put-down
- Bookworm, to a bully
- Bookworm, stereotypically
- Bookworm, scornfully
- Bookworm, perhaps
- Bookworm, maybe
- Bookish type, often
- Bookish persona
- Bookish person
- Black-sock wearer in gym, stereotypically
- Bill-Gates-to-be type?
- Bill Gates, snarkily
- Anyone who can speak Klingon, e.g.
- Academia nut?
- A real drip
- A jerk
- 4chan contributor, stereotypically
- "The ___," Shue play
- "The ___," 1987 Shue play
- "American ___" (Benjamin Nugent book)
- 'Big Bang Theory' type