Some of these rom-coms break the mold, showing characters navigating the unromantic complexities of relationships, finding happiness after a breakup and living life on their own terms. With others, there may be some romance in the mix, but a fairytale ending isn’t necessarily inevitable. Here are 25 hilarious and empowering romantic comedies for Valentine’s Day, perfect for singles or any rom-com fan!
1. Forgetting Sarah Marshall
In this raunchy yet sweet romantic comedy, Peter (Jason Segel) flees to Hawaii after being dumped by his actress girlfriend, Sarah (Kristen Bell). Hijinks ensue when Peter finds out that Sarah and her new boyfriend are staying at the same hotel. But ultimately, the movie reminds us that there is always hope after a breakup.
2. Under the Tuscan Sun
When Frances (Diane Lane) finds out that her husband has been cheating on her, she goes on vacation to Italy and ends up buying a villa in Tuscany. There are romantic elements to the movie, but the film is more about how Frances thrives on her own after her divorce.
3. Legally Blonde
A sorority girl tries to win back her boyfriend by following him to Harvard Law School, and soon realizes she’s way better off without him. Plus, she excels as a law student.
4. Bridesmaids
Brilliant female characters take center stage in this comedy about Annie Walker (Kristen Wiig), a single woman in her 30s whose life takes a turn when her best friend asks her to be her maid of honor.
5. Dan In Real Life
Dan (Steve Carell), a widower and single dad falls for a new woman, but there’s one catch: She’s his brother’s girlfriend.
6. (500) Days of Summer
What happens when you find The One, and you lose her? That’s the question driving this sweet, offbeat indie film that follows the breakdown of a relationship.
7. He’s Just Not That Into You
This rom-com with an ensemble cast deals with all the complexities and miscommunications of romantic relationships.
8. Love Actually
This beloved ensemble comedy portrays all different kinds of love stories, including relationships that just don’t work out. It’s a sweet reminder that happiness comes in different forms.
9. How to Be Single
This flick (based on an amazing book) follows a group of 20-something New Yorkers navigating single life in the big city. Oh, and if you’ve figured out how to be single by the end, please let us know.
10. The First Wives Club
This hilarious and empowering comedy follows three divorced women, played by Diane Keaton, Goldie Hawn and Bette Midler, as they seek revenge against husbands who left them for younger women.
11. Bridget Jones’s Diary
Bridget’s adventures in singledom are hilarious and relatable, and the movie remains a sweet reminder to hold out for the one who loves you–just the way you are.
12. Mamma Mia!
What’s not to love about a girls’ night in singing ABBA songs? Sure, there’s plenty of romance in this movie along with the singing, but the film is just as much about the complex relationships between women of different generations.
13. Breakfast at Tiffany’s
Nearly six decades after its release, this classic film remains a fresh, clever take on the life of a single young woman in New York City.
14. Amélie
This quirky, charming French film follows the adventures of a single woman living in Paris who tries to find love and help others while overcoming her own shyness.
15. 50 First Dates
A serial womanizer falls for an art teacher with amnesia who doesn’t remember their dates the following day–so he has to find ways to win her over again and again. It’ll remind you to wait for someone who’s willing to do the work.
16. Friends With Benefits
A pair of best friends, played by Mila Kunis and Justin Timberlake, decide to take their friendship to the next level. They quickly realize that a no-strings “friends with benefits” relationship isn’t as easy as it seems.
17. How Stella Got Her Groove Back
A successful stockbroker (Angela Bassett) falls for a man half her age on vacation and begins to question her priorities in life.
18. Always Be My Maybe
High school sweethearts reconnect 15 years later and things get complicated in this fresh, funny Netflix original film starring Ali Wong and Randall Park.
19. The Break-Up
A couple breaks up but neither one of them wants to leave their condo, so they continue living together as roommates.
20. Celeste and Jesse Forever
Celeste and Jesse married young after being high school sweethearts, but they now find themselves drifting apart. They separate, but swear to remind friends, in this bittersweet rom-com that captures the complexity of breakups.
21. Crazy, Stupid, Love
A middle-aged man finds himself back on the dating market after his wife of 25 years divorces him after cheating with a coworker.
22. Someone Great
In this Netflix movie starring Gina Rodriguez, “someone great” doesn’t necessarily equate to a romantic partner. In fact, it starts with an unexpected breakup and follows three female friends as they realize that love doesn’t always have to be romantic.
23. Knocked Up
This movie leans heavily on comedy but there is definitely some romance in there. We love it because said romance is so rocky, and in the end, it’s totally unclear if they’ll ever get back together.
24. My Best Friends Wedding
The kingpin when it comes to rom-coms, My Best Friend’s Wedding has us rooting for a resolution for this unrequited love. But unlike most rom-coms make it appear, this movie proves love isn’t that simple.
25. The Object of My Affection
Nina loves George. George loves Nina…as a friend. Because George is gay. Their relationship is hard to watch. But in the end, it’s worth it. Does your loved one love Outlander? We have 25 sweet gift ideas for an Outlander fan!
