Rom-Com March Madness: Make Your Picks for the Emotional Elite 8!

March Madness may be canceled, but here at ET, we’re making our own bracketology!

Everyone’s looking for TV and movies to watch as they self-quarantine and practice social distancing, so we’ve rounded up some of the best romantic comedies you can watch on streaming, ranked them, and are running a rom-com Sweet 16, single elimination-style, and letting you pick the winner.

After a somewhat surprising first round, which included 10 Things I Hate About You trouncing retro fave Clueless and Notting Hill claiming a shocking victory in the Julia Roberts showdown, the round of eight includes a hotly-debated Meg Ryan-off, a battle of the Brits and more!

Check out the match-ups below, cast your votes on the Twitter polls, and check back every day as we crown a champion!


When Harry Met Sally vs. You’ve Got Mail

It’s a second round Meg Ryan-off! Is she better with Billy or more terrific with Tom? Is it better to start off as friends or rivals? Make your pick!

Where to Watch: Stream When Harry Met Sally on Hulu and rent or buy You’ve Got Mail on Amazon Prime Video.

Crazy, Stupid, Love vs. 10 Things I Hate About You

This one’s a face-off of overbearing fathers and hunky male leads. Plus, Hannah Weaver and Kat Stratford would have totally been BFFs, right?

Where to Watch: Stream Crazy, Stupid, Love on Hulu and 10 Things I Hate About You on Disney+.

Notting Hill vs. Love, Actually

Battle of the Brits! Do you prefer your Hugh Grant as a bumbling-but-charming book shop owner or a bumbling-but-charming prime minister? Tough call, but someone’s gotta make it.

Where to Watch: Stream Notting Hill  and Love, Actually on Hulu.

How to Lose a Guy in 10 Days vs. Friends With Benefits

A perfect encapsulation of the difference between the early ’00s and early ’10s rom-com trends: Dating a guy on assignment from your job at a very important fashion magazine, vs. sleeping with your friend and swearing not to catch feelings. Guess what? You’re gonna fall in love either way.

Where to Watch: Stream How to Lose a Guy in 10 Days and Friends With Benefits on Hulu.


From a Julia Roberts ’90s showdown to a face-off between those two films that both came out in 2011 and both star one half of a now-married couple and are both about “friends” trying to have “benefits” without getting any “strings attached,” the first round of voting was full of interesting showdowns.

1. When Harry Met Sally  vs.  16. Definitely, Maybe 

It’s a Cinderella story to be sure, but these two have more in common than it might seem. Both movies are told over the course of several decades (and relationships) and both center their final confession of love around the ever-romantic notion of meeting the right person years before you realize that they’re actually the one. Swoon.

Where to Watch: Stream When Harry Met Sally and Definitely, Maybe on Hulu. 

2. You’ve Got Mail  vs.  15. To All the Boys I’ve Loved Before

Send it in an anonymous email like Shopgirl, or hand-write a love letter like Lara Jean, this old-school/new-school matchup is all about finding literary love where you least expect it.

Where to Watch: Rent or buy You’ve Got Mail on Amazon Prime Video and stream To All The Boys I’ve Loved Before on Netflix.

3. Crazy, Stupid, Love  vs.  14. Crazy Rich Asians

What’s a love story without a little family interference? These two “crazy” films navigate the question of soulmates, the way intergenerational drama plays out in modern romance, and, on a much shallower note, the undeniable perks of having a super-hot, super-wealthy beau.

Where to Watch: Stream Crazy, Stupid, Love and Crazy Rich Asians on Hulu.

4. Clueless  vs.  13. 10 Things I Hate About You

It’s Jane Austen vs. William Shakespeare in this battle of the modern-day literary adaptations. Too good to be true? As if!

Where to Watch: Rent or buy Clueless on Amazon Prime Video and stream 10 Things I Hate About You on Disney+.

5. Runaway Bride  vs.  12. Notting Hill

Barring maybe Meg Ryan, there’s no one person who encapsulates the power of the ’90s rom-com better than Julia Roberts. This matchup is a tough one, but go with your heart: Are you a runaway bride who’s ready to make it to the end of the aisle, or are you just a girl, standing in front of a boy, asking him to love her?

Where to Watch: Rent or buy Runaway Bride on Amazon Prime Video and stream Notting Hill on Hulu.

6. The Holiday  vs.  11. Love, Actually

In another timeline, The Holiday is one of the subplots included in Love, Actually‘s adorable anthology of holiday romances. (Think about it: an unlucky-in-love Brit and an uptight American swap houses and find romance, with swoonworthy accents and heart eyes abounding.) But in this reality, you have to choose your Christmas charmer — so, which is it?

Where to Watch: Stream The Holiday and Love, Actually on Hulu. 

7. How to Lose a Guy in 10 Days  vs.  10. 13 Going on 30

You can’t get much more early-’00s than these two. Charming female lead, whose character works at an Important Fashion Magazine™, a hunky love interest who will be an Oscar nominee in a few years, and an unconventional love story that’s just never going to work out…until it does! If it’s possible to already be nostalgic for this era, we totally are. 

Where to Watch: Stream How to Lose a Guy in 10 Days and 13 Going on 30 on Hulu.

8. Friends With Benefits  vs.  9. No Strings Attached 

No, they’re not the same movie. Yes, one is better — but no one can agree which. We can only imagine that this is an ongoing point of contention in the Kutcher-Kunis household.

Where to Watch: Stream Friends With Benefits and No Strings Attached on Hulu. 


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