Valentine’s Day Favorites
When you’re looking for Valentine’s Day viewing, most any romantic movie will fit the bill, but if you’re searching for something specifically set on the holiday, here are some suggestions…
Updated: February 2, 2025
Eternal Sunshine of the Spotless Mind (2004) - One of my favorite, genre-bending films, it’s perfect Valentine’s viewing for cynics and romantics alike. Not only is it set mostly on the eve of the holiday, Jim Carrey has never been better as he’s paying to forget, yet still trying to remember, Kate Winslet, in this twisty tale.
Sleepless in Seattle (1993) - A holiday-defying classic, is it a Christmas movie? A Valentine’s Day movie? How about all of the above? Taking its cue from An Affair to Remember (see below), this classic ends with a Valentine’s Day-destined meeting on the Empire State building.
An Affair to Remember (1957) - So, is this a cheat since it’s also on my New Year’s movie list? Well, maybe, but it still counts. Cary Grant and Deborah Kerr’s classic romantic drama spans holidays, and that’s just fine.
Obvious Child (2014) - While it sounds like more of an anti-Valentine’s day movie, the feat it takes to make a genuinely lovely (and funny!) rom-com about a Valentine’s Day abortion is truly worthy of a holiday viewing.
The Thing About Harry (2020, Freeform) - High school rivals reconnect when they road trip together to their mutual friend’s Valentine’s Day engagement party. The first LGBTQ holiday movie from a major cable channel, this set-over-multiple-Valentine’s Day title plays more like an indie feature, than a made-for-TV movie.
The Lost Valentine (2011, CBS) - This Hallmark Hall of Fame movie is one of the last network holiday films Hallmark made. Starring Betty White and Jennifer Love Hewitt, this multi-generational romantic movie is sure to bring tears to your eyes.
A Valentine Carol (2007, Lifetime) - Anya from Buffy is planning her Valentine’s Day wedding, but the ghost of her dead friend shows up to let her know she’s marrying the wrong guy.
Holiday in Handcuffs (2007, Freeform) - But, wait, isn’t this a Christmas movie? Sure, but while most of this crazy-pants romp is set over that other holiday, it closes out on Valentine’s Day, making it the perfect Noel-Cupid combo.
Some Like it Hot (1959) - This legendary Billy Wilder classic begins with Jack Lemmon and Tony Curtis witnessing the St. Valentine’s Day massacre, which is what forces them to go on the run in drag. But, don’t worry, it’s an all-time great comedy classic, and one of Marilyn Monroe’s most iconic roles.
Four Weddings and a Funeral (1994) - Does any part of this take place on Valentine’s Day? Well, it spans at least a year or two so…Probably, if you squint? Regardless, it’s the absolute best rom-com of all time in my book, so well worth watching on February 14th, or any other day.
The Simpsons: I Love Lisa (1993, FOX) - This season 4 episode, with the now classic “I Choo Choo Choose You” card, works perfectly as a stand alone Valentine’s Day special.
Be My Valentine, Charlie Brown (1975, CBS) - Probably the 4th-best of the original Charlie Brown holiday specials, after Halloween, Christmas and Thanksgiving (Yeah, in that order…I said what I said.)
Bob’s Burgers: Bob Actually (2017, FOX) - As with its classic Christmas episodes, Bob’s Burgers has had quite a few really good episodes set around Valentine’s, but this Love Actually rife with everyone getting their own slightly connected story is the most fun, and works even if you’re not deeply immersed in the larger show.
Madly Madagascar (2013, DVD) - This spin-off special has all the original voices from the movie, and is far better than you’d expect for a direct-to-DVD animation outing.
Cathy’s Valentine (1989, CBS) - Believe it or not, I remember watching this based-on-the-comic-strip special as a kid, and it’s got a few good laughs.
The Snoopy Show: Well, I’ll Be a Brown-Eyed Beagle (2022, Apple TV+) - This new animated special sees Snoopy playing matchmaker. All of these Apple entries have been really well done, and are truly in sync with the spirit of the original Charlie Brown specials.
For Better or Worse: A Valentine from the Heart (1993, CTV) - You can easily find this little-known, Canadian animated special in its entirety on YouTube.
The Muppets Valentine Special (1974, ABC) - This long-lost special was included on a 2007 DVD set of The Muppet Show. Though it aired as a one-off special, featuring guest star Mia Farrow, it served as the first pilot for The Muppet Show, which began in 1976.
Winnie the Pooh: A Valentine For You (1999) - Slight, but sweet, animated holiday special
A Charlie Brown Valentine (2002) - This modern Charlie Brown special can’t compete with the classics, but is still solid, animated holiday viewing for kids.
If you’re looking to bring a little girl power to your holiday celebration, grab a group of gal pals, a bottle of wine, and check out my favorite you-go-girl, funny films.
Muriel’s Wedding (1994) - One of the all-time great romantic comedies, where the real romance is the one between best friends.
First Wives Club (1996) - A stellar cast—Goldie Hawn, Bette Midler and Diane Keaton—plus this one still really holds up.
9-5 (1980) - Speaking of great casts and holding up…Dolly Parton, Jane Fonda and Lily Tomlin making the world a better place by stringing Dabney Coleman up to a garage door opener still works.
Pitch Perfect (2012) - Sassy singing and plenty of laughs.
Bridesmaids (2011) - Kristen Wiig, Maya Rudolph, Melissa McCarthy…What more do I have to say?
Mamma Mia! (2008) - It’s impossible not to sing along to this silly Meryl Streep classic, making for a guaranteed good time.
Girls Trip (2017) - Broad comedy, but definitely not stupid. (OK, that one scene on the zip line is bad.)
Someone Great (2019) - Part 20-something rom-com, but mostly about female friendship, this is an R-rated winner.
Whip It (2009) - Elliot Page and Drew Barrymore make this woman-centered sports movie work.
Wine Country (2019, Netflix) - While I wanted this Amy Poehler-directed movie, which stars so many amazing comedians, to be better, it’s still a good time.
BONUS: And, of course, there is always classic Parks and Rec season 2 episode, “Galentine’s Day,” which helped popularize the term. (There’s a second good, but not as good, “Galentine’s Day” Parks and Rec episode in season 6.)
More Centered on the Holiday
Valentine’s Day (2010) - This Garry Marshall Love Actually rip off is, if anything, even worse than his other effort, New Year’s Eve, but it is still holiday-set, light entertainment that gets better with a glass of wine or three.
I Hate Valentine’s Day (2009) - This re-teaming of Nia Vardolos and John Corbett definitely did not recreate the magic of My Big Fat Greek Wedding, to say the least, but it is set on the holiday. Still, this is actually just a recommendation to watch My Big Fat Greek Wedding instead. That one definitely holds up as a truly funny rom-com with outstanding chemistry.
Blue Valentine (2010) - The only thing holiday about this is the title, but this well-done, yet deeply dark, portrait of a marriage spiraling out of control is an option that will make anyone feel more than fine about being single on any holiday.
The Other Zoey (2023) - Mild mis-ID rom-com that takes place over Valentine’s Day weekend, with a whole lot of V-Day exposition. Features both Andie McDowell, in the mother role, and a focus on Hugh Grant rom-coms, but totally misses making a joke about Andie and Hugh’s most famous one…Which feels like it could have been the best part of an extremely mid movie.
Valentine (1979) - Made-for-TV movie starring Danny DeVito about the goings on in a retirement home.
On Valentine’s Day (1986) - Second in the Horton Foote trilogy, and currently available on Amazon Prime.
Funny Valentine (2005) - Indie starring Anthony Michael Hall
Overnight (2012) - Strangers meet on a redeye flight on Valentine’s Day
What Love Is (2007) - Cuba Gooding Jr. comedy about a guy dumped on Valentine’s Day
Valentine’s Day Refugees (2007) - A bonkers-sounding movie that combines faith and fantasy, that has an ugly creature named “Ghoulee" searching for love on Valentine’s Day and running into “Bible-quoting goth girls.”
The Valentine’s Day That Almost Wasn’t (2015) - Super weird and creepy puppet special, ostensibly for children. (And, if that description makes you curious, it’s currently on Amazon Prime.)
Big Mouth: My Furry Valentine (2019, Netflix) - This very much not-for-kids animated series isn’t normally my cup of tea (gross out/discomfort humor not really my thing), but this special does highlight all the smarter, funnier parts of this observational adolescent world.
Pete the Cat: A Very Groovy Valentine (2020, Amazon Prime) - Original Amazon special, featuring the beloved children’s book character
If You Give a Mouse a Valentine’s Cookie (2020, Amazon Prime) - There’s one of these for almost all the holidays now, but they’re still sweet, if-this, then-that fun.
Michael Bolton’s Big Sexy Valentine’s Day Special (2017, Netflix) - This is dumb fun, mostly because Bolton is so very much in on the joke.
Looney Tunes Cartoon Valetine’s Extwavaganza! (2022, HBO Max) - New Looney Tunes holiday special from HBO Max.
Harley Quinn: A Very Problematic Valentine (2023, HBO Max) - Holiday special from the adult, animated D.C. series.
My Funny Valentine (2000) - made-for-TV movie starring Julia Sweeney and Andrea Martin
Very, Very Valentine (2014, Hallmark) - Danica McKellar and Cameron Mathison.
Be My Valentine (2013, Hallmark) - Billy Baldwin is a fireman/widower.
Valentine Ever After (2016, Hallmark) - Community service turns to love for Autumn Reeser.
Valentine in the Vineyard (2019, Hallmark) - The third movie in the series starring Rachael Leigh Cook.
Dater’s Handbook (2016, Hallmark) - Though I have seen it, not entirely sure this Meghan Markle-starring movie actually has anything to do with Valentine’s Day, but it was part of Hallmark’s “Countdown to Valentine’s Day” line-up that season—and every season since, given Markle’s now-royal profile. It’s also one of Hallmark’s better made-for-TV rom-coms.
My Secret Valentine (2018, Hallmark) - Another vineyard set Hallmark Valentine movie, starring Lacey Chabert.
Love Locks (2017, Hallmark) - This Hallmark Hall of Fame entry stars real-life husband and wife, Rebecca Romijn and Jerry O’Connell.
All Things Valentine (2016, Hallmark) - Sarah Rafferty is a blogger who falls in love with a veterinarian.
Valentine’s Again (2017, Hallmark, a.k.a. Once Upon a Winter’s Date) -Nicky Whelan and Greg Vaughan are caught in a V-Day date time loop.
A Valentine’s Match (2020, Hallmark) - Bethany Joy Lenz and Luke Macfarlane fall in love.
Matching Hearts (2020, Hallmark) - Taylor Cole is a matchmaker falling for Ryan Paevey
The Secret Ingredient (2020, Hallmark) - Erin Cahill and Brendan Penny compete in a Valentine’s Day baking contest.
Playing Cupid (2021, Hallmark) - A school’s Valentine matchmaking project helps a parent and teacher fall in love.
Sweeter than Chocolate (2023, Hallmark) - Eloise Mumford makes magic cupid chocolates.
Welcome to Valentine (2023, Hallmark) - A pre-Valentine’s Day road trip leads to love.
An Unexpected Valentine (2025, Hallmark) - Lacey Chabert and Robert Buckley meet cute searching for the owner of a lost engagement ring..
It Happened One Valentine’s (2017, a.k.a. Love Exclusively) - Made-for-TV movie from director Jake Helgren, about a tabloid reporter who falls in love with a pop star.
Valentine’s Date (2021) - Action comedy from Maverick Entertainment, now on Amazon Prime
Down (2019, Hulu) - Horror-suspense set on Valentine’s where a woman finds out the person she’s trapped in an elevator with is her stalker.
My Valentine (2020, Hulu) - When three people get locked in a concert hall on Valentine’s Day, personal grievances turn violent.
My Bloody Valentine (1981) - Because it wouldn’t be a holiday, without a horror movie taking place on it.
My Bloody Valentine (2009) - The inevitable slasher movie remake.
Valentine (2001) - Another V-Day-set horror tale.
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