| 100% | BULLDURHAM | 10 | 1988 romantic comedy featuring a love triangle with Susan Sarandon, Kevin Costner, and Tim Robbins (2 wds.) |
| 54% | BROADCASTNEWS | 13 | 1987 romantic comedy featuring a love triangle with Holly Hunter, William Hurt, and Albert Brooks (2 wds.) |
| 47% | MOONSTRUCK | 10 | 1987 romantic comedy featuring a love triangle with Cher, Nicolas Cage, and Danny Aiello |
| 42% | MAYBESOMEDAY | 12 | 2014 novel by 33-Across featuring a love triangle with college student Sydney, her boyfriend, and her neighbor: 2 wds. |
| 35% | ITENDSWITHUS | 12 | 2016 novel by 33-Across featuring a love triangle with florist Lily, her boyfriend, and an old flame: 4 wds. |
| 33% | BULLDURHAM | 10 | 1988 Kevin Costner/Susan Sarandon baseball movie: 2 wds. |
| 30% | WARMBODIES | 10 | A 2013 paranormal romantic comedy starring Nicholas Hoult - whose birthday it is today - as a zombie who falls in love with a human: 2 wds. |
| 30% | LOVEACTUALLY | 12 | 2003 holiday romantic comedy with Martin Freeman as a stand-in actor: 2 wds. |
| 30% | MYSTICRIVER | 11 | 2003 movie set in Boston, for which Sean Penn and Tim Robbins each won a 1-Across: 2 wds. |
| 29% | BREAKFASTCLUB | 13 | 1985 John Hughes comedy featuring five students during a Saturday detention, with "The": 2 wds. |
| 29% | CHASINGAMY | 10 | 1997 romantic comedy directed by Kevin Smith, starring Ben Affleck and Joey Lauren Adams: 2 wds. |
| 29% | PEETA | 5 | Part of a love triangle with Katniss and Gale |
| 29% | ILSA | 4 | Character in a love triangle with Victor and Rick |
| 28% | ALOT | 4 | "___ Like Love," a 2005 romantic comedy starring Ashton Kutcher and Amanda Peet: 2 wds. |
| 27% | THEGRADUATE | 11 | 1967 romantic comedy film starring Dustin Hoffman and Anne Bancroft based on a Charles Webb novel of the same name: 2 wds. |
| 27% | THEBODYGUARD | 12 | 1992 romantic drama starring Kevin Costner and 34-Across (2 wds.) |
| 27% | MEANGIRLS | 9 | 2004 teen comedy featuring a clique called the Plastics: 2 wds. |
| 26% | DURHAM | 6 | "Bull ___" (baseball film starring Susan Sarandon and Kevin Costner) |
| 26% | ICEAGE | 6 | Animated film featuring a mammoth and a sloth: 2 wds. |
| 26% | ALLTHEREIS | 10 | 1996 romantic comedy, "Love is ___," starring Angelina Jolie which is a modern retelling of "Romeo and Juliet": 3 wds. |
| 25% | WAYNESWORLD | 11 | 1992 comedy featuring Rob Lowe as a sleazy TV producer: 2 wds. |
| 25% | ROBINHOOD | 9 | Role for Errol Flynn, Kevin Costner, and Russell Crowe: 2 wds. |
| 25% | EDDIEMURPHY | 11 | He played Prince Akeem (and other roles) in the 1988 romantic comedy "Coming to America": 2 wds. |
| 25% | HORRIBLEBOSSES | 14 | 2011 Jennifer Aniston comedy featuring Jamie Foxx as a "murder consultant": 2 wds. |
| 25% | LORENZOSOIL | 11 | 1992 film starring Nick Nolte and Susan Sarandon as parents of a sick boy: 2 wds. |
| 25% | PITCHPERFECT | 12 | 2012 musical comedy featuring an a cappella singing group called the Bellas: 2 wds. |
| 25% | PALMSPRINGS | 11 | Hulu romantic comedy about a California wedding weekend gone wrong: 2 wds. |
| 24% | ENCINOMAN | 9 | 1992 comedy featuring 15- and 34-Across: 2 wds. |
| 24% | SCREAMQUEENS | 12 | 2015-2016 Fox dark comedy featuring Niecy Nash-Betts as a sorority's security guard: 2 wds. |
| 24% | ADAMSANDLER | 11 | Jennifer Aniston's costar in the 2011 romantic comedy "Just Go With It": 2 wds. |