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October 23, 2026

Our top 5 romantic comedies (You've Got Mail made both lists, in different spots)

We each ranked five romantic comedies without comparing notes. You've Got Mail is the only film on both lists, but we didn't rank it the same.

For our top five rom-coms, we agreed on the ground rules before we agreed on anything else: wholesome, funny, actually a comedy, not just a drama with a couple of jokes in it (sorry, Sense and Sensibility, that one's not eligible). Princess Bride came up too, and we both agreed it's hilarious and also not a rom-com. See the full ranked list.

Jeff's list, bottom to top: She's All That, Crazy, Stupid, Love, (500) Days of Summer, You've Got Mail, and his number one, 10 Things I Hate About You. He's a sucker for the secret-bet plot that runs through both She's All That and 10 Things, and says the Taming of the Shrew retelling still brings him back to being a kid who thought the world was his oyster.

Matt's list, bottom to top: To All the Boys I've Loved Before, Runaway Bride, Hitch, Notting Hill, and his number one, You've Got Mail. You've Got Mail was also his very first movie date, which tells you how long he's carried the torch for it.

You've Got Mail is the only film that made both lists, but it landed in different spots: Jeff has it at number two, Matt has it at number one. Both of us think Nora Ephron's retelling of The Shop Around the Corner beats the original, and we're both a little amazed by how much the film plays like a time capsule now. Matt pointed out our kids would have no idea what "you've got mail" even refers to; Jeff figures you could remake the whole plot today with someone catfishing someone else on Snapchat.

Past that one overlap, we didn't match on a single other pick, and our number ones couldn't be more different in tone. Matt's top choice is a sweet, old-fashioned love story; Jeff's is a teen comedy set in a fictional Tacoma high school he insists looks nicer than the actual rectangular prism he went to. Matt got a kick out of 10 Things I Hate About You's dad, a gynecologist who can't stop reminding his daughters to be safe, and he almost left his own number-three pick, Hitch, off the list entirely before deciding Kevin James and Allegra Cole's subplot was too good to cut.

We also talked briefly about why we don't see many true rom-coms made anymore. These days the genre mostly shows up dressed as something raunchier, closer to The Hangover or Bridesmaids, which is fun in its own way but isn't quite what either of us meant by rom-com this week.

Hear the full breakdown, along with our reviews of Sense and Sensibility and Tenzing, on episode 7.

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