| Napoleon III, to Napoleon | 25 |
| Macaulay Culkin, to Bonnie Bedelia | 34 |
| Lot, to Abraham | 15 |
| Lot to Abraham | 15 |
| Jason Sudeikis, to George Wendt | 31 |
| Huey, Louie or Dewey | 20 |
| Huey, Dewey or Louie, to Donald Duck | 36 |
| Huey, Dewey or Louie, to Donald | 31 |
| Huey, Dewey or Louie, notably | 29 |
| Enoch, to Seth | 14 |
| Cohan, to Uncle Sam | 19 |
| Certain heir | 12 |
| Brother's son | 17 |
| One hiring relatives | 20 |
| Bookworm | 8 |
| Wimp's cousin | 17 |
| Wonk | 4 |
| Uncool fellow | 13 |
| Unlikely prom king | 18 |
| Square, updated | 15 |
| Eggheady sort | 13 |
| Uncool collegian | 16 |
| Overly bookish sort | 19 |
| Geeky type | 10 |
| Geeky sort found within this puzzle's four longest answers | 62 |
| Geeky one | 9 |
| Computer geek | 13 |
| Taped-eyeglasses wearer | 23 |
| Socially challenged person | 26 |
| Geeky guy | 9 |
| Computer geek, e.g. | 19 |
| Bully's prey, traditionally | 31 |
| Unlikely party animal | 21 |
| Unlikely class president | 24 |
| Square figure? | 14 |
| Scholastic stereotype | 21 |
| Pocket-protector wearer, stereotypically | 40 |
| Overly bookish type, stereotypically | 36 |
| Mathlete, stereotypically | 25 |
| Jock's antithesis | 21 |
| Inept individual | 16 |
| High school bookworm, stereotypically | 37 |
| Dweeby sort | 11 |
| Bully's target | 18 |
| Whom a bully may bully | 22 |
| Unlikely prom king candidate | 28 |
| Unlikely candidate for prom king | 32 |
| Unhip type | 10 |
| Teen comedy stereotype | 22 |
| Techie, traditionally | 21 |
| Stereotypical sci-fi fan | 24 |
| Pocket protector wearer, in stereotypes | 39 |
| Eggheady sort, stereotypically | 30 |
| Dweeb's cousin | 18 |
| Brainy, socially inept sort | 27 |
| Bookworm, in stereotypes | 24 |
| Bookish type | 12 |
| "Happy Days" put-down | 31 |
| Unpopular sort | 14 |
| Unhip person | 12 |
| Uncool fellow, stereotypically | 30 |
| Uncool character | 16 |
| Trekkie, to some | 16 |
| Taped eyeglasses wearer | 23 |
| Steve Urkel, for one | 20 |
| Stereotypically uncool collegian | 32 |
| Stereotypical computer programmer | 33 |
| Square type | 11 |
| Society oddball | 15 |
| Socially inept type | 19 |
| Socially awkward type | 21 |
| Social lightweight | 18 |
| Social dud, stereotypically | 27 |
| Sci-fi conventiongoer, stereotypically | 38 |
| Role in many teen flicks | 24 |
| Pocket-protector sporter, stereotypically | 41 |
| Pocket-protected one of stereotypes | 35 |
| Pocket protector wearer, perhaps | 32 |
| One who's not in | 20 |
| One who ruins the curve, stereotypically | 40 |
| One lacking social graces | 25 |
| Obsessive type | 14 |
| Modern misfit | 13 |
| IT guy, stereotypically | 23 |
| Inept individual, stereotypically | 33 |
| Ineffectual person | 18 |
| In-group outcast | 16 |
| In-crowd outcast | 16 |
| High school misfit | 18 |
| Hardly a hipster | 16 |
| Guy with little chance at a supermodel, stereotypically | 55 |
| Future CEO | 10 |
| Dweeb's pal | 15 |
| Dweeb's kin | 15 |
| Computer geek, for instance | 27 |
| Bully's target, often | 25 |
| Bully's target, maybe | 25 |
| Bully's prey, perhaps | 25 |
| Bookish sort | 12 |
| "Kick me" sign wearer, stereotypically | 48 |