From ‘The Holiday’ to ‘Holidate’: 5 Christmas Movies to Watch on Valentine’s Day

While Christmas movie sticklers may argue about While You Were Sleeping’s place in the holiday movie canon (it starts on Christmas Day and ends after New Year’s), this one is undeniably an A-list romcom — no matter which holiday you assign to it. It stars queen Sandra Bullock, her first of many smash hit romcoms, as a tollbooth operator who saves her crush (Peter Gallagher) from getting crushed by a train. Now this stranger is in a coma, the family presumes Sandy’s his fiancee — and, to top it all off, this dude has an equally handsome and even more charming brother (Bill Pullman). It’s a helluva premise with way more attention paid to love and laughs than anything holly or jolly.

Where to watch While You Were Sleeping

The Christmas season serves as a backdrop for this irresistible international romance. Set before the era of Airbnb, Cameron Diaz and Kate Winslet play two strangers who arrange to swap houses (and countries) for the holidays in order to escape their heinous relationship troubles. A California girl (Diaz) in jolly old England and a Brit (Winslet) in sunny Los Angeles — there’s your comedy. The Holiday then deftly handles two simultaneous romances as Diaz falls for Jude Law and Winslet is swept off her feet by Jack Black at peak hotness. This is a star-studded affair that’s a delight no matter when you watch it.

Where to watch The Holiday

Now that we’ve got two classics on this list, let’s turn our attention to some newer holiday movies that you may have missed over the past few years, starting with Netflix’s Holidate. This one stars Emma Roberts and Luke Bracey as two acquaintances who strike up a pact: instead of spending very holiday miserable and alone, they’ll be each others’ plus ones to all of the dumb parties they’re obligated to attend. It’s a strictly platonic, mutually beneficial relationship and there’s no way it’ll become anything more. Sure. And if the premise doesn’t intrigue you, know that Kristin Chenoweth plays an out of control aunt in this one.

Where to watch Holidate

When it comes to holiday romcoms, no one comes close to touching Hallmark. The network is a romcom machine, turning out 40+ every holiday season. Of all of the ones from recent years, though, A Kiss Before Christmas is the one you’ll want to check out even after you’ve taken the tree down. Teri Hatcher and James Denton (a Desperate Housewives reunion!) play a married couple stuck in a relationship rut. But then, a little Christmas magic gives them the opportunity to see what their lives would have been like had they not met all those years ago. Sure, that’s a very Christmas-y premise, but the chemistry between Hatcher and Denton is truly timeless.

Where to watch A Kiss Before Christmas

This Prime Video original is barely two months old, but it’s worth watching again or checking out if you missed it in December. While the movie’s cinematography acts as a love letter to New York City during the holidays, the premise is really evergreen: a Tiffany’s bag mix-up leaves an engagement ring in the wrong hands and leads to an unintended — yet accepted! — proposal from a slacker BF to his put-together GF (Zoey Deutch). When the ring’s real owner (Kendrick Sampson) realizes what’s happened, he has to figure out a way to get his engagement ring back… and work up the nerve to bust this faux-engaged couple’s bubble. But what if, Sampson’s character starts to wonders, the mix-up put his ring on the right woman’s finger…?

Where to watch Something From Tiffany's