| Like an ill-mannered kid | 24 |
| Like an ill-tended garden | 25 |
| Like an illegal boxing blow | 27 |
| Like an immodest bathing suit | 29 |
| Like an impartial inheritor? | 28 |
| Like an impossible situation | 28 |
| Like an impromptu speech | 24 |
| Like an inaugural ball | 22 |
| Like an inconvenient tire | 25 |
| Like an ineffective threat | 26 |
| Like an infamous Dallas knoll | 29 |
| Like an infant agewise | 22 |
| Like an infested warehouse | 26 |
| Like an infielder's glove | 29 |
| Like an inflexible agreement | 28 |
| Like an inscribed monument | 26 |
| Like an inscribed pillar | 24 |
| Like an insincere compliment | 28 |
| Like an insomniac's night | 29 |
| Like an instant replay | 22 |
| Like an insufficient account | 28 |
| Like an interstate highway | 26 |
| Like an intimate dinner | 23 |
| Like an NBA power forward | 25 |
| Like an O. Henry ending | 23 |
| Like an oboe in sound | 22 |
| Like an oboe's sound | 24 |
| Like an oboe's tones | 24 |
| Like an oboe, but not a sax? | 28 |
| Like an obsessive collector | 27 |
| Like an obsessive mind | 22 |
| Like an octopus' defense | 28 |
| Like an octopus's defense | 29 |
| Like an oeil-de-boeuf window | 28 |
| Like an off-pitch piano | 23 |
| Like an old Andean empire | 25 |
| Like an old apple, maybe | 24 |
| Like an old bucket of song | 26 |
| Like an old Frankfurter | 23 |
| Like an old Norse poem | 22 |
| Like an old schoolhouse | 23 |
| Like an old tree trunk | 22 |
| Like an old wristwatch? | 23 |
| Like an onion in a Gibson | 25 |
| Like an opossum's tail | 26 |
| Like an optimist's glass | 28 |
| Like an oral exam, often | 24 |
| Like an otological test | 23 |
| Like an otter's feet | 24 |
| Like an outdated license | 24 |
| Like an outdoor painting | 24 |
| Like an outdoorsy Englishman | 28 |
| Like an overcast night | 22 |
| Like an overripe melon | 22 |
| Like an oversized magazine? | 27 |
| Like an overventilated room | 27 |
| Like an owl's eyes | 22 |
| Like an owl, proverbially | 25 |
| Like an S.R.O. theater | 22 |
| Like an unbelievable story | 26 |
| Like an uncaught escapee | 24 |
| Like an unchallenged receiver | 29 |
| Like an uncleaned fireplace | 27 |
| Like an uncleaned hearth | 24 |
| Like an undeliverable pkg. | 26 |
| Like an undercooked egg | 23 |
| Like an underdone steak | 23 |
| Like an undistinguished hotel | 29 |
| Like an unflipped fried egg | 27 |
| Like an unfortunate torero | 26 |
| Like an unfriendly stare | 24 |
| Like an unhelpful explanation | 29 |
| Like an uninhabited preserve | 28 |
| Like an unmatched sock | 22 |
| Like an unopened Zinfandel | 26 |
| Like an unrinsed washer load | 28 |
| Like an unspoiled paradise | 26 |
| Like an unswept fireplace | 25 |
| Like an unswept hearth | 22 |
| Like an untended garden | 23 |
| Like an unusual occurrence | 26 |
| Like an unweeded garden | 23 |
| Like an unwelcome diplomat | 26 |
| Like an unwritten exam | 22 |
| Like an uphill battle? | 22 |
| Like an upraised eyebrow | 24 |
| Like anatomical anvils | 22 |
| Like ancient canyon cliffs | 26 |
| Like Andersen's duckling | 28 |
| Like Anderson Cooper, finally | 29 |
| Like andirons, generally | 24 |
| Like angels we have heard? | 26 |
| Like angry Captain Kangaroo? | 28 |
| Like Anna's students | 24 |
| Like Annapolis civilians | 24 |
| Like Annie's lizards | 24 |
| Like annoying salesmen | 22 |
| Like Anon's output | 22 |
| Like antiques at an auction | 27 |
| Like Antoine's cuisine | 26 |