14 Days of Swooon

The Ultimate Rom-Com Revealed: And the Winner of Our Bracket Is…

All the votes are in, and the time has come. Swooon’s rom-com bracket has finally reached its conclusion after 14 Days of Swooon.

This month, to celebrate the holiday all about love, we’ve talked to some of the romance community’s most iconic names from The Bachelor’s own Grant Ellis to the queen of romance television herself Mindy Kaling.

Most importantly, all of you, our loyal readers and voters, decided on which rom-com reigns supreme. We started out with 64 rom-coms, and all 584 of you narrowed down the films after making tough choices between your favorite romantic comedies. (One voter said Clueless vs. How to Lose a Guy in 10 Days was like “putting the ’96 Bulls against the ’17 Warriors in round one.”)

Our final four movies were: Pretty Woman, While You Were Sleeping, When Harry Met Sally, and Sleepless in Seattle. With rom-com heavyweights like Sandra Bullock, Julia Roberts, and Meg Ryan in the mix, this quartet face-off wasn’t a surprise.

After the final votes were placed, the top two movies left were When Harry Met Sally and While You Were Sleeping. Talk about a nailbiter.

In the head-to-head matchup of Ryan and Billy Crystal vs. Bullock and Bill Pullman, who came out on top?

The result (drumroll, please)… When Harry Met Sally.

The 1989 romantic comedy unsurprisingly took home the bacon, wagering the question: Can two attractive people really just be friends? In Harry and Sally’s case, absolutely not. From the white fisherman sweater to New Year’s Eve kiss, When Harry Met Sally has cemented itself as one of the most iconic romantic comedies of all time. So iconic that the two stars reunited this year for a Super Bowl ad spot reenacting the iconic orgasm scene in Katz’s Deli.

When Harry Met Sally follows the years-long love story of two people who “hated each other” upon their first meeting as they drove from Chicago to New York together after the suggestion of Harry’s girlfriend, who was also Sally’s friend. As their hatred turned into friendship, Harry and Sally saw each other through their relationships, their breakups, and eventually their own romance.

Iconically set in New York fall, the film takes place against the backdrop of the tides of New York City, mutual friends’ own blossoming relationships, and the transformation from college graduate to full-fledged adult. The love story isn’t without its own setbacks, running the gauntlet of commitment issues, miscommunications, one night stands, and saved-by-the-bell midnight kisses. Funny and sweet, this is undoubtedly a rom-com you can rewatch a thousand times over and not get sick of it. You know, after all this When Harry Met Sally talk, we think it might be time for our next rewatch. Until next year!