24 Romantic Comedies to Watch for a Valentines Date Night

I asked, you answered, and I was blown away by the responses. It seems you guys all jumped at the idea of a date night movie checklist, so I though why not? Valentine’s Day is just around the corner and a Valentine’s Day movie checklist is a perfect way to celebrate!

Though it can never rival the Family Movie Night tradition, my husband and I love filling our free time snuggling up on the couch, making some popcorn, and watching our favorite films. It’s not as easy for us to get out of the house right now so putting the kids to bed early and enjoying a some time alone is usually as good as it gets.

Buttttt… my husband and I have very different tastes in movies so it can often take a full feature-length of time before we’ve even picked what we’re going to watch! But there are a few romantic comedy classics that we can both agree on (or that I overruled him on) so I’ve made that list and I’m bringing it here to you! I’ve included some great genre bridgers on this list as well as some lesser-known favorites that I’m sure you’ll love!

Ready to see the ultimate Valentine’s DAY movie checklist?

You can download and print off my Valentine’s Day movie checklist right here. See if your picks make the cut!

10 Things I Hate About You

Adapted from William Shakespeare’s play “The Taming of the Shrew,” 10 Things I Hate About You is smart, witty, and hilarious. Everything you want in a romcom. A pretty, popular teenager can’t go out on a date until her ill-tempered older sister does.

50 First Dates

A man afraid of commitment finally meets his perfect girl. Henry and Lucy hit it off until Henry discovers the woman of his dreams has short-term memory loss and forgets their date the next day.

A Knight’s Tale

Another movie inspired by an old literary classic, A Knight’s Tale based on Geoffrey Chaucer’s “The Canterbury Tales” is an action-packed adventure that sees a lowly peasant reimagine himself as a knight, and find romance along the way.

Always Be My Maybe

A brilliant 2019 Netflix original, everybody thought Sasha and Marcus would end up together except for Sasha and Marcus. After re-meeting 15 years later, the pair start to think maybe the time is right.

Couples Retreat

Four couples head off to a tropical resort. One of the couples is there to work on their marriage, the other three are devastated to hear that the resort’s therapy sessions aren’t compulsory.

Crazy Rich Asians

Based on a global bestseller, this crazily fast romantic comedy follows native New Yorker Rachel Chu to Singapore to meet her boyfriend’s family. You’ll love Awkwafina in this as the hilarious best friend, but there’s also a lot of heart and family ties in this movie.


This is a good Valentine’s Day movie choice as it explores the mystical journey of a young elemental guardian as they embark on a quest to restore balance to a world threatened by elemental chaos.

Failure to Launch

A 35-year old is still living with his parents until they hire an interventionist to help him graduate out of the house. Cue several intertwining love stories, and we have a rom-com classic.


Ever dates someone with a secret? Well, in this romantic action-adventure comedy, Cole (played by Chris Evans) discovers Sadie is a secret agent! Watch this Valentine’s Day movie for some laughs and love as they get swept on an international adventure.


Will Smith stars as a smooth-talking man who falls for a workaholic columnist. Oh, and all while helping a shy accountant woo a beautiful heiress. Plus the 90%/10% rule is a classic!

How to Lose a Guy in 10 Days

Benjamin Barry bets that he can make a woman fall in love with him in 10 days. Andie Anderson is writing a story on how to lose a guy in 10 days. So what’ll happen when the pair meet one another and start to fall in love?

Jerry Maguire

A sports agent has a moral epiphany and evaluates his life. Very few stick by him in this feel-good film. “You had me at ‘hello.”

Love and Basketball

There have been two constants in Monica and Quincy’s lives. Each other and basketball. It’s a one-on-one game with high stakes.

Love Simon

A coming-of-age tale with a difference. Simon Spier keeps a huge secret from his family, his friends, and all of his classmates: he’s gay. Simon has a love connection with a boy, Blue, by email, but the only problem is that Simon has no idea who he’s talking to.

My Best Friend’s Wedding

When a woman’s long-time friend reveals he’s engaged, she realizes she loves him herself and sets out to get him, with only days before the wedding.

Someone Great

Another Netflix original. After a break up on the eve of her big move away, Jenny enjoys one last NYC adventure with her two best pals. A great story about love and friendship.

Something Borrowed

Secrets are revealed, and friendships are broken when terminally single Rachel falls for Dex, her best friend Darcy’s fiancé.

Something New

Kenya McQueen is a successful African-American CPA, but her life has become all work and no play. Urged on by her friends to try something new, she goes on a wild blind date, but it’s far from love at first sight!

Sweet Home Alabama

New York fashion designer Melanie played by Reese Witherspoon suddenly finds herself engaged to the city’s most eligible bachelor. She’s just got one problem; she needs to return to Alabama to divorce her childhood sweetheart first. But things aren’t what they seem.

The Princess Bride

A young boy’s grandfather reads him the story of a farm boy-turned-pirate who encounters numerous obstacles in his quest to be reunited with his true love.

Think Like a Man

Four friends get together to turn the tables on their partners after finding out the ladies are using Steve Harvey’s relationship advice against them.

To All the Boys I’ve Loved Before

A teenage girl writes letters to all of her past loves. They’re meant for her eyes only. When the letters get out, she’s confronted by her exes one by one.

While You Were Sleeping

Chicago L-train ticket seller Lucy saves her long-time crush who falls onto the tracks. At the hospital, she’s mistaken for his fiancé while he’s still in a coma. The lies become too entangled, and things get even crazier when Lucy falls for her crush’ brother.


Download and print my ULTIMATE Valentine’s Day movie checklist by clicking here!


Not into printing things? That’s ok too! You can download it to your phone and check off the boxes as you go that way too. Looking for a smaller version to share on Instagram? Check out my Instagram Story highlights!


Several of these romcom classics are available to watch on Disney+. Are you ready to sign up? I have all of the details on how you can get a discounted rate on Disney+ here.

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