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There’s nothing like a sweet romantic comedy to get you into the Valentine’s Day spirit. These 10 movies captured hearts and wallets, eventually earning major cash at the box office. Check out the highest-grossing rom-coms, per iMDB’s BoxOfficeMojo, below.

10. Knocked Up

Though it’s not your typical hearts and flowers romance, this R-rated Judd Apatow film starring Katherine Heigl and Seth Rogen captured hearts and brought in major viewers. The 2007 film, about a couple who fall in love after a one night stand leads to a pregnancy, made $30,690,990 on its opening weekend, with a lifetime gross of $148,768,917 during its time in theaters.

9. Runaway Bride

Julia Roberts + Richard Gere = box office gold. The Garry Marshall story about a woman who has left multiple men at the altar and the reporter who falls in love while telling her story earned $35,055,556 when it opened in 1999 and eventually grossed $152,257,509.

8. Sex and the City

When the love story of Carrie Bradshaw and Mr. Big got the Big screen treatment, it also made Big bucks. The 2008 movie starring Sarah Jessica Parker, Cynthia Nixon, Kim Cattrall, Kristin Davis, and Chris Noth made $57,038,404 in its opening weekend. As of 2025, had a lifetime gross of $152,647,258.

7. The Proposal

Sandra Bullock and Ryan Reynolds joined forces in this 2009 rom-com, where Bullock plays a businesswoman who attempts to marry her beleaguered assistant to avoid being deported to Canada. The comedy, which also stars Betty White and Mary Steenburgen, made $33,627,598 on its opening weekend and went on to a lifetime gross of $163,958,031.

6. Crazy Rich Asians

The most recent rom-com to break the top 10 is 2018’s Crazy Rich Asians, starring Constance Wu and Henry Golding. Based on the novel by Adele Lim and directed by Jon M. Chu, who would go on to direct Wicked, the film made $26,510,140 on its opening weekend with a lifetime gross of $174,532,921.

5. There’s Something About Mary

Another R-rated entry, this Ben Stiller and Cameron Diaz film from the Farrelly brothers caught hearts like a zipper caught on… well, something else. It made $13,740,644 in its opening weekend in 1998 and $176,484,651 in its lifetime gross.

4. Pretty Woman

The film that made Roberts and Gere an “it” duo, also directed by Garry Marshall, came out in 1990 and made $11,280,591 in its opening weekend. The story of a businessman and a sex worker who fall in love achieved a lifetime gross of $178,406,268 during its theatrical run.

3. Hitch

Will Smith stars as a “date doctor” who helps men set themselves up for success with the women of their dreams. Eva Mendez is the reporter determined to expose him. The 2005 rom-com made $43,142,214 when it opened and has a lifetime gross of $179,495,555.

2. What Women Want

Nancy Meyers’ 2000 film stars Mel Gibson as a chauvinistic ad executive who gets the power to read women’s minds. The romantic comedy made $33,614,543 on its opening weekend and eventually earned $182,811,707.

1. My Big Fat Greek Wedding

An unexpected smash hit, this 2002 comedy was written by star Nia Vardalos and was made on a budget of $5,000,000. (For contrast, What Women Want had a budget of $70,000,000.) In its opening weekend, it made only $597,362, but it went on to become a huge success, grossing a whopping $241,438,208.