| Like a required course, maybe | 29 |
| Like a respectful librarygoer | 29 |
| Like a responsible math teacher? | 32 |
| Like a restaurant that serves panang curry | 42 |
| Like a restless sleep | 21 |
| Like a restrained dog | 21 |
| Like a retail item | 18 |
| Like a retired barber? | 22 |
| Like a retired cashier? | 23 |
| Like a retired clerk? | 21 |
| Like a retired insurance agent? | 31 |
| Like a retired musician? | 24 |
| Like a retired prof. | 20 |
| Like a retired seismologist? | 28 |
| Like a revealing bathing suit | 29 |
| Like a revealing skirt, maybe | 29 |
| Like a reversible jacket that's been reversed | 49 |
| Like a rhinestone cowboy? | 25 |
| Like a rhino or unicorn | 23 |
| Like a rhythmic beating | 23 |
| Like a rich custard | 19 |
| Like a rich milkshake | 21 |
| Like a rickey | 13 |
| Like a rickey's taste | 25 |
| Like a right not exercised | 26 |
| Like a rimrock | 14 |
| Like a rind | 11 |
| Like a rising star | 18 |
| Like a risky situation | 22 |
| Like a river bottom | 19 |
| Like a river delta | 18 |
| Like a road full of furrows | 27 |
| Like a road in a Frost poem | 27 |
| Like a road runner | 18 |
| Like a road section with a flagger, maybe | 41 |
| Like a roadway after an ice storm | 33 |
| Like a Roald Dahl tale | 22 |
| Like a robin's egg | 22 |
| Like a robot's voice | 24 |
| Like a roc | 10 |
| Like a roc? | 11 |
| Like a rock | 11 |
| Like a rock band | 16 |
| Like a rock star's lifestyle | 32 |
| Like a rocker on tour too long, perhaps | 39 |
| Like a Rockettes show | 21 |
| Like a rogue elephant | 21 |
| Like a roguish child | 20 |
| Like a Rolek watch | 18 |
| Like a Rolez watch | 18 |
| Like a roller-coaster ride | 26 |
| Like a Rolls, say | 17 |
| Like a Rolls-Royce | 18 |
| Like a Roman atrium | 19 |
| Like a Roman tyrant | 19 |
| Like a romantic dinner | 22 |
| Like a romantic evening, maybe | 30 |
| Like a romantic night | 21 |
| Like a Romeo's adventures | 29 |
| Like a Romney | 13 |
| Like a rondeau | 14 |
| Like a roofer's drinks? | 27 |
| Like a room at Schönbrunn Palace | 39 |
| Like a root-beer float | 22 |
| Like a rose | 11 |
| Like a rose bush | 16 |
| Like a rotten apple | 19 |
| Like a rotunda | 14 |
| Like a rough, harsh voice | 25 |
| Like a rout, for the losing team | 32 |
| Like a rowboat that's adrift | 32 |
| Like a royal flush | 18 |
| Like a royal wedding | 20 |
| Like a rubberneck route | 23 |
| Like a rubberneck's route | 29 |
| Like a Rubens model | 19 |
| Like a ruby | 11 |
| Like a rude remark | 18 |
| Like a ruffle | 13 |
| Like a rug that can only be cleaned once | 40 |
| Like a rugby ball | 17 |
| Like a rugged bug? | 18 |
| Like a ruined roux | 18 |
| Like a runcible spoon | 21 |
| Like a runner-up, often | 23 |
| Like a running back after a game | 32 |
| Like a runt | 11 |
| Like a runway model | 19 |
| Like a rustic cabin on a cold night | 35 |
| Like a rustling skirt, perhaps | 30 |
| Like a saber | 12 |
| Like a sachet | 13 |
| Like a sacker of Rome | 21 |
| Like a sad sack | 15 |
| Like a sailor avoiding the draft? | 33 |
| Like a sailor on leave | 22 |
| Like a saint's head | 23 |
| Like a Salmon P. Chase bill, slangily | 37 |
| Like a samaritan's help | 27 |
| Like a sandal | 13 |