| With one's hands full | 25 |
| With one's head held high | 29 |
| With one's heart on one's sleeve | 40 |
| With one's heart, if nothing else | 37 |
| With one's identity hidden | 30 |
| With one's jaw on the floor | 31 |
| With one's jaw on the floor, so to speak | 44 |
| With one's mouth open | 25 |
| With one's sweetie, say | 27 |
| With only ~66,000 inhabitants, it's still the second most populous city in Montana | 86 |
| With op, a computer manager | 27 |
| With open mouth | 15 |
| With open palms, maybe | 22 |
| With open ___ | 13 |
| With open ___ (in a friendly way) | 33 |
| With opposing aims | 18 |
| With optimism | 13 |
| With optional subtitles, as a TV show | 37 |
| With opulence | 13 |
| With others (abbr.) | 19 |
| With our compliments | 20 |
| With outstanding bills | 22 |
| With panache | 12 |
| With parsley, on menus | 22 |
| With parsley, perhaps | 21 |
| With passion | 12 |
| With pasta, in product names | 28 |
| With patience | 13 |
| With penitence | 14 |
| With pep and agility | 20 |
| With pep in one's step | 26 |
| With perfect timing | 19 |
| With perfection | 15 |
| With persistence | 16 |
| With Petrarch, a team | 21 |
| With petulance | 14 |
| With Picchu, a place in Peru | 28 |
| With picking, trivial fault-finding | 35 |
| With pictures: Abbr. | 20 |
| With piety | 10 |
| With pleasing effect | 20 |
| With pleasure | 13 |
| With plenty of space | 20 |
| With plenty to chew on | 22 |
| With plenty to spare | 20 |
| With pluck | 10 |
| With Pogo, Okanagan monster | 27 |
| With pond, Newfoundland community | 33 |
| With Port, place in Prince Edward Island | 40 |
| With precise timing | 19 |
| With precision | 14 |
| With prejudice | 14 |
| With premeditation | 18 |
| With press and public barred | 28 |
| With pretentious display | 24 |
| With pretentiousness | 20 |
| With pride, it's a member | 29 |
| With proficiency | 16 |
| With profundity | 15 |
| With prongs | 11 |
| With prudence | 13 |
| With punctilio | 14 |
| With Pursuit, Haney and Abbott invention | 40 |
| With puzzlement | 15 |
| With quick awareness | 20 |
| With quick wit | 14 |
| With quite the figure | 21 |
| With rage | 9 |
| With raised letters | 19 |
| With ramifications | 18 |
| With rancor | 11 |
| With rapid tempo | 16 |
| With real effort | 16 |
| With real rudeness | 18 |
| With really long odds | 21 |
| With reason | 11 |
| With reckless abandon | 21 |
| With reference | 14 |
| With reference to (legalese) | 28 |
| With refinement | 15 |
| With regard to | 14 |
| With regard to surface space | 28 |
| With regard to worth | 20 |
| With regard to, on memos | 24 |
| With regret | 11 |
| With regrets | 12 |
| With regularity | 15 |
| With regularity, in odes | 24 |
| With regularity, in poetry | 26 |
| With regularity, to Whitman | 27 |
| With relevance | 14 |
| With relevance, to a lawyer (literally, "to the thing") | 65 |
| With relish | 11 |
| With reluctance | 15 |
| With remorse | 12 |
| With repercussions | 18 |
| With repugnance | 15 |
| With resentment | 15 |
| With reservations | 17 |
| With reserve | 12 |