| Wonk, maybe | 11 |
| Urkel of Family Matters for one | 39 |
| Unpopular student | 17 |
| Unlikely homecoming king | 24 |
| Unlikely escort for a prom queen | 32 |
| Unlikely clique member | 22 |
| Unhip one | 9 |
| Uncool student | 14 |
| Uncool kid | 10 |
| Uncool bookworm | 15 |
| Typical Rick Moranis film role | 30 |
| Twerp's next of kin | 23 |
| Twerp or jerk | 13 |
| Totally unhip type | 18 |
| This may be hard to date | 24 |
| Teen-movie persona | 18 |
| Teen outcast | 12 |
| Teen movie stereotype | 21 |
| Techie, often | 13 |
| Techie, maybe | 13 |
| Target of taunts | 16 |
| Swot : Britain :: ___ : America | 31 |
| Swot | 4 |
| Swirlie victim, perhaps | 23 |
| Studious sort, and proud of it | 30 |
| Steve Urkel on "Family Matters," e.g. | 47 |
| Stereotypical sporter of a pocket protector | 43 |
| Stereotypical science student | 29 |
| Stereotypical pocket-protector wearer | 37 |
| Stereotypical Mensan | 20 |
| Stereotypical computer hacker | 29 |
| Square of a sort | 16 |
| Square hidden in each of the five long across answers | 53 |
| Societal klutz | 14 |
| Socially ineffectual person | 27 |
| Social washout | 14 |
| Social outcast, maybe | 21 |
| Social oddball | 14 |
| Social greenhorn | 16 |
| Social bungler | 14 |
| Slashdot reader, maybe | 22 |
| Single-minded sort | 18 |
| Single-minded person | 20 |
| Simp of a sort | 14 |
| Screech or Urkel | 16 |
| Scholastic sort, perhaps | 24 |
| Role-playing game player, stereotypically | 41 |
| Rick Moranis in "Ghostbusters," e.g. | 46 |
| Revenge-seeker of film | 22 |
| Quiz bowl lover, say | 20 |
| Propeller-head | 14 |
| President of the Chess Club, to some | 36 |
| Poindexter type | 15 |
| Pocket-protector sporter | 24 |
| Pocket protector purchaser | 26 |
| Pi Day celebrant, perhaps | 25 |
| Pharrell Williams's rap group | 33 |
| Person who may be "adorkable" | 39 |
| Person who gets picked on | 25 |
| Overly techie type | 18 |
| Overly brainy sort | 18 |
| Overly bookish sort, stereotypically | 36 |
| Overly academic type | 20 |
| One with no hope in a popularity contest | 40 |
| One whoÂ’s unhip | 19 |
| One who's socially clueless | 31 |
| One who's socially challenged | 33 |
| One who might snort when he laughs | 34 |
| One who might celebrate Towel Day | 33 |
| One who might celebrate Pi Day | 30 |
| One socially challenged | 23 |
| One needing social work? | 24 |
| Oddball of a sort | 17 |
| No sophisticate he | 18 |
| No jock | 7 |
| Napoleon Dynamite, for one | 26 |
| Napoleon Dynamite, e.g. | 23 |
| Modern square | 13 |
| Mathlete, perhaps | 17 |
| Many a Pi Day celebrant | 23 |
| Many a character on "The Big Bang Theory" | 51 |
| Lover of brain games | 20 |
| Lout: Slang | 11 |
| Jock's counterpart | 22 |
| Internet addict, perhaps | 24 |
| Intellectual sort | 17 |
| In-crowd outsider | 17 |
| High-school put-down | 20 |
| High school bookworm, in stereotypes | 36 |
| Hardly The Fonz | 15 |
| Hardly a BMOC | 13 |
| Guy with his nose always stuck in a book | 40 |
| Grade school designation | 24 |
| Geek's cousin | 17 |
| Filmdom's Napoleon Dynamite, for one | 40 |
| Feckless fellow | 15 |
| Excessive studier | 17 |
| Encyclopedia reader from A to Z, say | 36 |
| Eggheady sort, in stereotypes | 29 |
| Dweebish sort | 13 |