Set It Up
About a pair of overworked personal assistants who rig their bosses to fall in love, Set It Up has a pair of charming leads and a small arsenal of winking rom com jokes. Trust us though, you’re going to want to enjoy this one with your favorite piece of delivery pizza. You’ll thank us later.
To All the Boys I’ve Loved Before
Sure, this one is geared toward a high school crowd, but its sharp writing, genuinely sweet storytelling and charming family dynamics make it a great watch no matter how old you are.
When We First Met
This rom-com with a sci-fi twist imagines what it would be like to be able to relive your first encounter (over and over again) with the one that got away. It’s laugh-out-loud funny, but has redemptive undertones about regret, correcting past wrongs and fighting for true love.
Win It All
Jake Johnson’s Win It All is a love story masking as a poker movie. The film tells the story of a 30-something guy who just can’t get his life together, and the woman who finally convinces him that settling down and finding love is worth the gamble.
A classic, especially as the weather turns cold (has a movie had a better collection of coats and jackets??), Love Actually is the rare ensemble rom com that balances all its stories and delivers satisfying payoff across its network of narratives. It’s sweet and comforting, like a warm dessert.
It’s hard to summarize the plot of this gem of a tearjerker, but if you love music—or are just looking for a moving story about love, family and hope—than look no further than August Rush.
Rumor Has It…
It might not have the compulsive watchability as some of our other picks, but Rumor Has It… still boasts Jennifer Aniston and Mark Ruffalo amid its Graduate-knockoff story. There’s no chance it lives up to the classic that inspired it, but it’s good for a breezy DIY date night.
How to Lose a Guy In 10 Days
One of the many adapted Shakespearean tales of the late 1990s and early 2000s, Lose a Guy pits pre-renaissance Matthew McConaughey against prime Kate Hudson. The premise is absurd, but it’s a fun bottleneck for high jinks, and that’s why we’re here. Bring crunchy snacks.
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