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In the mood for a good movie night? These are the best romantic comedies that will have you laughing, crying and swooning with ease…
We all love a good movie night and I love my big block-buster action movies as much as the next guy (probably even more!) but sometimes there is nothing like cozying up under a blanket and putting on a good romantic comedy.
So if you’re looking to go on your next big, swoony, romantic journey (with lots of laughs along the way), here are some pretty amazing rom-coms you’ll definitely enjoy. From rom-com classics like Moonstruck to hilarious flicks like Set it Up, these movies will have you laughing, crying and swooning!
30 Best Romantic Comedies to Watch On Movie Night
The Proposal (2009)
The Proposal is very very beloved here at May the Ray which is why it is getting the top spot. The Proposal follows Margaret who is basically the worst boss in the world. She is a control freak who likes the position of power she is in just a little too much. When an issue with her visa threatens to have her deported, she enlists the help of her assistant Andrew (who probably hates her the most!). To stops herself from getting deported Margaret asks Andrew to marry her. In the effort to get to know each other better, chaos and hijinks ensue, but also maybe a little love?
Crazy Rich Asians (2018)
Nick Young and his girlfriend Rachel Chu, travel to Singapore for the marriage of his best friend. There Rachel discovers that Nick has been kind of keeping a big secret from her, Nick’s family is actually extremely wealthy. One of the wealthiest in Singapore in fact. And let’s just say they don’t approve of Nick’s American girlfriend. . .
Set it Up (2018)
Two employees Harper and Charlie, exhausted by their demanding jobs and employers come up a plan that’ll hopefully distract their bosses and ease their stress. The plan is to set up their bosses with each other (with the hopes that they fall in love) so that they can focus less on their jobs and more on each other. With the plan seemingly succeeding, Harper and Charlie also begin to realize that they may be falling for each other as well, which was NOT part of the plan. . .
She’s All That (1999)
This is your classic popular guy falls for unpopular girl story. But it’s become a classic for a reason! She’s All That basically follows popular class president Zack Siler after he is dumped by his girlfriend for a reality tv star. He then makes a bet with a friend that he can turn Laney Boggs, a talented artist (and the school nerd) into the next prom queen. What he wasn’t expecting was to fall in love with her while doing so. . .
Crazy, Stupid, Love (2011)
Crazy, Stupid, Love follows the stories of two couples, that interweave in both a hilarious and heartwarming way. One couple is Cal and Emily a middle-aged, long-time married couple that are potentially facing a divorce. And the other couple is Jacob and Hannah, two young people who meet in a bar and have an instant connection. Crazy, Stupid, Love follows the hilarious way that Cal and Jacob meet and the way that Jacob (a raging playboy) teaches Cal how to confidently seduce women so that he can get over his divorce. But a bump in the road is hit when Jacob begins to genuinely fall in love and starts to question his playboy status, and Cal realizes the woman he loves and doesn’t want to lose is his wife. . .
Leap Year (2010)
Leap Year is a hilarious movie about love and finding oneself (with the beautiful backdrop of Ireland!). So basically in the movie, Anna decides to fly all the way to Ireland to surprise and propose to her long time boyfriend. She does this because there is this Irish myth that if you propose on February the 29th (leap day) the person you propose to will definitely say yes. But in true rom-com fashion, it’s not as plain and simple as that. Her flight gets diverted because of a storm and she ends up meeting this grumpy inn-keeper who agrees to drive her to Dublin (and her boyfriend). Their journey, while filled with ups and downs and so many hilarious moments, allows them to slowly get to know each other and also face everything they’ve been running from in their own lives.
My Big Fat Greek Wedding (2002)
I remember growing up, I was never allowed to watch this movie, all I could do was catch snippets here and there and the scenes I do remember watching were hilarious. As an adult who is in control of her viewing choices, I was able to fully watch the movie. . . I’m just in awe of how a movie made then still manages to be funny and actually good today! My Big Fat Greek Wedding is just about all the chaos that ensues when a girl who comes from very a big (and very traditionally) Greek family decides to marry a very white (and very non-Greek) man. . .
Just Friends (2005)
Just Friends is a hilarious romantic comedy that starts with Chris (an obese high-school senior) who attempts to declare his feeling for his long time bestfriend Jamie but is instead humiliated by the jock and laughed at by the entire school. This pushes him to leave town and never look back. . . But years (and a ton of weight-loss) later, a successful Chris returns to his hometown and tries to reconnect with Jamie. He’s efforts to woo her get increasingly funnier but at the end of the day he comes to realize that Jamie is no longer the same girl in she was in high school. . .
Think Like a Man (2012)
Think Like a Man is a hilarious take on what would happen if men had the the “cheat-codes” for women during dating. A group of men discover that women have been using the bestselling book Think Like a Man as a sort of guide to dating and men. The men decide to take advantage of this fact and make themselves into what the book describes as the perfect man. This leads to a lot of hilarity as the men slowly discover that lying is probably not the best way to get the girl. . .
The Holiday (2006)
Two life worn women decide to swap homes for bit, just so that they can get a break from their own lives for the holidays. The two soon realize that their homes (and lives) could not be more different! But when romance starts to bloom for both of them, they have to decide whether to stay for love or go back to the life they’re comfortable with!
Moonstruck (1987)
If the fact that Cher and freaking Nicholas Cage are in a rom-com together doesn’t convince you to watch this movie then I don’t know what will! Anyway Moonstruck basically follows Loretta who decides to get married again after the death of her first husband. Her fiancé Johnny is a nice, stable guy, just what she needs. But things go not quite according to plan when she meets his crazy, intense brother Ronny. . .
Yesterday (2019)
Yesterday follows a struggling musician who wakes up from a freakish accident to realize that somehow he is the only one who remembers The Beatles. He obviously takes advantage of this knowledge and uses it to rise to fame. But what he realizes is that fame and money don’t mean anything when you can’t be with the one you love. . .
Serious Moonlight (2009)
Growing up this was one of my favorite movies, I just loved how utterly chaotic this movie is! Serious Moonlight is about a woman (Louise) who discovers that her husband is about to leave her for another woman. So she insanely decides to tie him up and hold him captive in their house and force him to remember why they fell in love in the first place.
Overboard (1987)
A rich, spoiled heiress hires a carpenter to work on her yacht but then refuses to pay him. A freakish accident causes her to lose her memory and the carpenter decides to take advantage of the situation by convincing the heiress that she is actually his wife AND THE MOTHER TO HIS KIDS!
Forgetting Sarah Marshall (2008)
Forgetting Sarah Marshall is a hilarious movie about a guy who get broken up with by his long time girlfriend so that she can be with another man. Heartbroken, he decides to take himself on a vacation in Hawaii so that he can move on. But the hilarious part is that the resorts that he ends up at is the resort that his ex-girlfriend and her new fiancé are also vacationing at!
Always Be My Maybe (2019)
Always Be My Maybe is that amazing, heart-warming rom-com that also delivers on the funny moments too. It follows Sasha and Marcus, two old childhood friends who could have potentially had something more but they lost touch before anything could happen. Sasha goes on to become a rich and famous chef, while Marcus stayed in their home town and became a maintenance man. When Sasha returns to town, to open a new restaurant, the two end up reconnecting. Them reuniting brings back old feelings and memories from their difficult childhoods. But they work through them together and fall in love again!
What Happens in Vegas (2008)
Two people recently having the worst luck decide to go to Vegas to party away the misery. They meet when a computer error has them put in the same hotel room. The two decide to spend the night partying together (because why not?!). And after a night of drunken fun, end up getting married! In the morning they (obviously) realize what a giant mistake was made and decide to get a divorce. On the way out, one of them decides to make one last bet and ends up winning millions of dollars! The hilariousness unfolds when a meddling judges puts a complication on how they can split the money and whether or not they can divorce. . .
It’s a Boy Girl Thing (2006)
Two high school neighbors who absolutely despise each other get their lives flipped when an Aztec god curses them to swap bodies. The issue is that Woody is a popular jock and Nell is a total nerd. The movie hilariously follows Nell and Woody as they try to live out each others lives, while also trying to find a way to switch back!
The Bounty Hunter (2010)
Am I the only one with a soft spot for Gerald Butler in rom-coms??? Anyway The Bounty Hunter is about an ex-cop Milo, who’s life basically fell apart after divorcing his wife. He now collects bounties to make a living. When his ex-wife skips a court hearing to chase a story (she’s a reporter), a warrant is put out for her arrest. Milo gets a call to bring her in and is ecstatic because it means that he can get back at his ex for the divorce and also make money while doing it!
You’ve Got Mail (1998)
Kathleen Kelly is the owner of a tiny independent bookshop. In her personal life she meets this man the internet but they agree to keep their relationship anonymous. Despite this the two slowly fall in love as they learn more about each other. While this is going on a big bookstore chain opens up next door to hers, putting her business in jeopardy. This causes her to clash with the owner of the big bookstore. The two hilariously go back and forth but the shocker comes when it is revealed that the man she’s been talking to online and the owner of the big bookstore are the same person!
The Long Shot (2019)
Look with a Seth Rogan movie, I know I’m always going to laugh and this movie did not disappoint! So a struggling reporter (Fred) gets a lucky break when he runs into an old childhood friend (who just happens to be a successful politician) and she offers him a job as a speech writer. She plans to run for office and kinda needs help turning her image around. Fred happens to be just what she needs but his advice is unconventional at best. As they work together they reconnect and hilariously fall in love with each other.
Jumping the Broom (2011)
Sabrina Watson is the only child from a very rich family and she decides to marry a normal banker man from a. . . not so wealthy family. Things go out of control when during the wedding period their family and friends meet and the differences in lifestyle cause many hilarious clashes and differences in opinion about how things should be done! And of course its not a wedding rom-com without a good mom-ster-in-law. . .
Friends with Benefits (2011)
Two love jaded individuals decide to make a deal. Since they both do not want to be in relationships they agree to have sex with no strings attached, no feelings, no attachments, just friends with benefits. They get to expend all that sexual energy, but without the exhaustion of an actual relationship. It’s a win, win right? What could possibly go wrong?
Ten Things I Hate About You (1999)
An overprotective father lays down some rules. His popular high-school daughter cannot date until her loner anti-social older sister gets a boyfriend first. So someone pays the school bad-boy to date the older sister. But getting her to like him is a little bit harder than he anticipated. . .
Knight and Day (2010)
Knight and Day is a hilarious romantic comedy starring Cameron Diaz and Tom Cruise. It’s about a woman who is mistakenly thought to be in league with a rogue CIA agent when they have a random encounter at the airport. She becomes more entangled with him when he hijacks the plane she’s on. Having no choice but to go with him, they end up on this crazy journey to expose a world-ending plot, made hilarious by the fact that she does not belong in this intense action-filled world. . .
She’s the Man (2006)
When Viola’s girls football team is dissolved in favor of the boys football team at her school, she decides to pretend to be her twin brother so that she can sign up for rival schools team. The movie hilariously follows Viola as she trains and rooms with her new team members while pretending to be a boy. But things take a turn when Viola realizes she has feelings for one of the boys. . .
This Means War (2012)
When two best friends/CIA agents realize that they are unwittingly seeing the same woman, they decide to place a wager as to whom she will choose. This means no interfering in each others process and no sex until she decides. But their relationship is tested when each of them does crazier and crazier things to outdo the other and win the girl.
Stardust (2007)
Tristan, desperate for Victoria’s hand in marriage ,vows to find (and give her) a fallen star if she agrees to marry him. His plan goes a little left when he discovers that the fallen star is actually a human girl. His journey back to Victoria with the star girl is full of challenges but he slowly begins the realize that maybe Victoria is not the one for him. . .
What’s Your Number (2011)
Ummm a rom-com starring Chris Evans? Yes please! What’s Your Number follows a thirty something, down on her luck woman who finds an article that says that women who have slept with over 20 men will have trouble finding husbands. And Ally realizes that she recently slept with her twentieth man. So with the help of her hunky neighbor, they track down all her ex-partners with the hopes that one of the will take her back and possibly marry her so that her number doesn’t go up. But the whole journey makes her realize that maybe numbers aren’t everything and maybe the perfect guy was next door all along. . .
27 Dresses (2008)
I think this movie basically immortalized the phrase always a bridesmaid, never a bride. 27 Dresses follows Jane Nichols whose been a bridesmaid 27 times and has kept every single bridesmaids dress. Despite being a bridesmaid all those times, she’s never quite found that happy-ending love for herself until she meets a cynical journalist who doesn’t believe in love. . .
Confessions of a Shopaholic (2009)
A shopaholic, drowning in debt finds herself writing columns about money saving for a financial magazine. Her column becomes surprisingly successful and she finds herself falling in love with a wealthy entrepreneur, but her secret threatens to ruin her love life and career.
How to Be Single (2016)
Even though this isn’t a romantic comedy (more like a breakup comedy) it just had be on this list because it’s about the most important love of all, self-love (but it’s also pretty darn funny as well!). . .
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