| 100% | HOWDOYOUKNOW | 12 | 2010 Reese Witherspoon romantic comedy that flopped: 4 wds. |
| 41% | THISMEANS | 9 | "___ War," a 2012 romantic comedy starring Tom Hardy - whose birthday it is tomorrow - along with Reese Witherspoon: 2 wds. |
| 38% | THEUGLYTRUTH | 12 | 2009 Gerard Butler romantic comedy that costarred Katherine Heigl: 3 wds. |
| 37% | THINKLIKEAMAN | 13 | 2012 romantic comedy starring 15-Across: 4 wds. |
| 37% | ONTHEPLUSSIDE | 13 | 2023 romantic comedy novel by 26-Across that takes place within a fictional makeover show (4 wds.) |
| 36% | VALENTINESDAY | 13 | 2010 hit romantic comedy costarring 15-Across: 2 wds. |
| 34% | LEGALLYBLONDE | 13 | 2001 American comedy film starring Reese Witherspoon (birthday today) that was adapted from an Amanda Brown novel: 2 wds. |
| 34% | WAR | 3 | "This Means ___," a 2012 romantic comedy film starring Reese Witherspoon, Chris Pine and Tom Hardy |
| 33% | LEGALLYBLONDE | 13 | 2001 Reese Witherspoon comedy referenced in Ariana Grande's "thank u, next" music video: 2 wds. |
| 33% | THEMAKEUPTEST | 13 | 2022 romantic comedy novel by 26-Across that takes place at fictional Claymore University (3 wds.) |
| 33% | JUSTGOWITHIT | 12 | 2011 romantic comedy film directed by Dennis Dugan starring Jennifer Aniston and Adam Sandler: 4 wds. |
| 33% | BIGLITTLELIES | 13 | HBO drama series starring Reese Witherspoon that was based on a bestselling Liane Moriarty novel: 3 wds. |
| 33% | AWRINKLEINTIME | 14 | 2018 fantasy movie in which Reese Witherspoon played a being who flies kids through space: 4 wds. |
| 33% | SOMELIKEITHOT | 13 | The 1959 American romantic comedy film which had the iconic closing line, "Nobody's perfect": 4 wds. |
| 33% | JUSTGOWITHIT | 12 | 2011 romantic comedy film directed by Dennis Dugan which stars Nicole Kidman and Adam Sandler: 4 wds. |
| 32% | FRIENDSWITH | 11 | "___ Benefits," 2011 romantic comedy film that starred Justin Timberlake and Mila Kunis in the lead roles: 2 wds. |
| 32% | GONEGIRL | 8 | 2014 American psychological thriller co-produced by Reese Witherspoon that was adapted from a Gillian Flynn novel: 2 wds. |
| 32% | JERRYMAGUIRE | 12 | The 1996 American romantic comedy-drama sports film that popularized the line, "You had me at 'hello.'": 2 wds. |
| 31% | GIGI | 4 | 1958 romantic comedy that won Best Picture |
| 30% | BIGLITTLELIES | 13 | TV series with Reese Witherspoon and Nicole Kidman that is based on Liane Moriarty's novel of the same name: 3 wds. |
| 30% | ELLEWOODS | 9 | Reese Witherspoon's role in "Legally Blonde": 2 wds. |
| 30% | HOT | 3 | "___ Pursuit" (2015 Reese Witherspoon comedy) |
| 30% | LEGALLY | 7 | __ Blonde, a Reese Witherspoon comedy |
| 30% | INTRANSLATION | 13 | "Lost ___," a romantic comedy starring Bill Murray and Scarlett Johansson, that is considered one of the best movies of the 2000s: 2 wds. |
| 30% | HOWDOYOUKNOW | 12 | 2010 comedy-drama film starring Reese Witherspoon and Paul Rudd |
| 29% | HOME | 4 | "Sweet ___ Alabama" 2002 Reese Witherspoon comedy, |
| 29% | THISMEANSWAR | 12 | 2012 Reese Witherspoon action comedy |
| 28% | LEGALLYBLONDE | 13 | Reese Witherspoon film set at Harvard Law School (2 wds.) |
| 28% | EASYA | 5 | 2010 Emma Stone comedy: 2 wds. |
| 28% | DATE | 4 | With 6-Across, Carell/Fey romantic comedy of 2010 |