Best Christmastime Romantic Comedies
By Franki Hanke
There is plenty of romantic comedies set in the holiday season, so the hardest part is picking one! As a bit of a romantic comedy aficionado, I’m giving you this list ranked, so it gets better and better as you go down the list.
Of course, if you’re a lover of It’s a Wonderful Life, then please chase your small-town bliss, but when we’re hosting all the gals, we’re looking for a little love on screen (not a mental breakdown). For more traditional holiday recommendations, read Best Holiday Movies to Watch with Family.
Now, we’ve all got our own opinions on the best Christmas movies, so get in the holiday spirit and take my ranking with a grain of salt.
Best Romantic Christmas Movies
Single All The Way
Watching Single All The Way was a fun whiplash between excitement for a same-sex pairing in a holiday film and a realization that it’s campy to the point of awkwardness. Other than changing the character themselves, it’s as Hallmark as it comes with the main character Peter enlisting his best friend Nick to fake being his boyfriend to appease his family. That is until his mom sets him up with her hot spin instructor. Then, Peter’s all about Plan B: Nick is “just friends!” and bag the hot spin instructor.
Where to Watch Single All the Way: Stream it on Netflix.
Pairing Mackenzie Davis and Kristen Stewart in a modernization of the classic, bring-home-the-girlfriend trope, Happiest Season tries to be funny, but ends up entirely elsewhere.
Where to Watch Happiest Season: Stream it on Hulu.
Starring Reese Witherspoon and Vince Vaughn as a couple who usually avoid their families for Christmas, but have to attend after their annual vacation is called off due to a canceled flight. So, the unhappy couple attends each of their divorced parents’ four, separate Christmas celebrations.
The film is funny but cynical and bitter.
While You Were Sleeping
Like a fine, but very young, wine, While You Were Sleeping works in part because of its 90’s-decade charm. It stars Sandra Bullock as a train token collector with a long-standing crush on a regular commuter. The film kicks off when she saves his life from an oncoming train and lies that she’s his fiance to visit him in the hospital. Then, of course, all his loved ones arrive, so she keeps up the charade.
Where to Watch While You Were Sleeping: Stream it on Disney+.
If your main thought when watching a rom-com is, “That could be cheesier,” then you’ll love Serendipity. It’s a love story about fate with John Cusack as Jonathan and Kate Beckinsale as Sara. Jonathan thinks it’s love at first sight, but Sara won’t believe it without a sign. So, they separate and hope fate re-connects them. Does it? You’ll have to watch and see, huh?
Where to Watch Serendipity: Stream it on any platform with a STARZ subscription or rent on Amazon Prime Video for only $4.
Featuring two women (Cameron Diaz and Kate Winslet) in the same places of life (broken-hearted and off-men) but totally different geographies, The Holiday tells the story of trading places for the holidays for a change of scenery. They don’t expect to find new connections in these new places.
This Nancy Meyers film is delightfully genuine and surprisingly less cheesy than the genre’s norm.
Starring Queen Latifah, Last Holiday tells the story of Georgia a department store assistant who finds she only has a few weeks to live. She decides to spend all her money on a luxury holiday. It’s a total change of pace from your usual romantic comedies.
Where to Watch Last Holiday: Stream it on Amazon Prime Video.
The Family Stone
Sarah Jessica Parker, Diane Keaton, and Rachel McAdams mix for this family of celebrities in The Family Stone. The addition of Luke Wilson and his satisfying drawl makes it all work. The film follows an eccentric family stone when their son brings his uptight girlfriend home to meet the family. It’s a mix of slow-building flirtation and familial mayhem. What’s not to like?
Where to Watch The Family Stone: Stream it on any platform with a STARZ subscription or rent on Amazon Prime Video for only $4.
Love Actually asks the question, “Is it instantly a better movie by the inclusion of Colin Firth and Hugh Grant?” The answer is yes. With nine different, overlapping love stories, Love Actually captures the romance of the Christmas lead-up with a star-studded cast.
Christmas With You
If you’re a hard-core rom-com watcher, then you’ve probably seen them all. So, this year, watch something brand-new. Christmas with You is a November new release with Aimee Garcia as a pop star who visits a high school-aged fan to make her Christmas wish come true.
Where to Watch Christmas With You: Stream it on Netflix.
Released in 2021, Love Hard is a modern rom-com with Nina Dobrev. It tells the story of a relationship columnist who makes a spur-of-the-moment, romantic gesture to fly into town to meet up with Josh, her long-distance, dating app fling. But, when she arrives, she finds a different face behind the door. Turns out, he’d been cat-fishing her with a picture of his friend Tag.
With a cliche concept, Love Hard manages to be a fresh addition to the genre.
Where to Watch Love Hard: Stream it on Netflix.
With the most iconic soundtrack of any Christmas musical, White Christmas is a Christmas classic and romantic drama all in one. It stars Bing Crosby acting and singing alike.
If you haven’t already seen this iconic classic, it’s a must-watch.
Where to Watch White Christmas: Stream it on Netflix.
On the surface, the pairing of Emilia Clarke and Henry Golding’s love story in Last Christmas looks as classically feel-good as every other, but the playful Wham! soundtrack and the plot itself make this a refreshing change of pace.
Where to Watch Last Christmas: Stream it on Hulu Live TV.
Bridget Jones’s Diary
For a subtle nod to Christmastime by bookending the entire film with the holidays, Bridget Jones’s Diary is a comedic masterpiece led by Renee Zellweger as Bridget herself. She’s accompanied by the no-fail duo Colin Firth and Hugh Grant. Eye candy alone is enough to enjoy this one, but add in unwavering sarcasm and calamity and it’s a perfect kick-off to your marathon.
Where to Watch Bridget Jones’s Diary: Stream it on any platform with a SHOWTIME subscription.
When Harry Met Sally
I’m not alone in thinking this is the penultimate romantic comedy. Nora Ephron achieved greatness with When Harry Met Sally with a relatable, yet utterly romantic love story set against the backdrop of New York City at Christmastime (and New Year’s Eve) and a timeless soundtrack.
It follows Billy Crystal as Harry and Meg Ryan as Sally in a long-time friendship that simmers slowly into a love story you actually believe. It’s heartwarming enough to fight off the December chill.
Where to Watch When Harry Met Sally: Stream it on Netflix.
Now, pick a movie and get your popcorn popping! It’s gonna take quite the marathon to watch all of these before Christmas Day!
If you’ve still got five minutes before the movie starts, read The Impact of Family Holiday Traditions to learn why something as simple as a movie night can be so important.
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