Romantic comedies are always a safe bet for date nights. Just in case it’s news to you, most girls enjoy love stories. The Walt Disney Corporation has made more money than some countries telling young girls stories about Princesses, who with the help of some kind of quirky sidekick, are often able to find her one true love. Well, we’re all grown up now, and that plot line we’ve been watching for potentially decades? It’s still not old for us. While we’ve dropped that whole Princess act, and the cost of Disney paraphernalia has been replaced by rent, we venture into the world with some zany sidekicks of our own in search of our modern day Prince Charming. If you on the other hand are ready to break out of your When Harry Met Sally rut, here is a list of date tested, male approved romantic comedies that won’t have you nodding off beside her.
The movies mentioned below have all of the usual trappings of traditional rom-coms, but with a fun twist here and there, not to mention some stereotypical role reversals. There is even an Adam Sandler film that made the cut! (I know, we’re shocked too, can you guess what one?).
And just in case you needed an extra push, I’ve outlined reasons as to why she’ll like it and why you’ll love it. At the very least, now you have some new reasons as to why Deadpool really is the perfect date movie! All that’s left to do is grab some snacks, and start counting your brownie points. You’re welcome!
10. The Proposal
I’ll start with the good news for Andrew Paxton: He’s a college graduate who somehow magically landed a job in his chosen field post-graduation. The bad news? He is the assistant to mega-villain boss, Margaret Tate, Executive Editor in Chief of major book-publishing firm Colden Books. Margaret also has a problem: her visa has expired and she is about to be deported. Tate (portrayed by Sandra Bullock) blackmails Paxton (played by Ryan Reynolds) into a shot gun wedding, and heads to Alaska to meet Andy’s family, where their weekend mission is to convince everyone they’re in love.
Why he’ll love it: This hilarious cast includes appearances from comedy powerhouses including Craig T. Nelson, Oscar Nuñez, and Betty White, who all deliver laugh after laugh. The script is genuine, and wonderfully sarcastic. Oh, and you’ll have a whole new appreciation for Lil John’s 2002 hit Get Low (Thanks Betty!)
Why she’ll love it: You had us at Ryan Reynolds.
9. I Love You, Man
Now, the central relationship in this movie might be a “bro-mance”, but it follows the general plot development of a romantic comedy; so you might be able to sneak it in. Peter Klaven is on Cloud 9, he just proposed to the woman of his dreams and she said “Yes!” Now Peter, (played by Paul Rudd) has a problem: he’s always been quick to make friends with women, but there’s no one he can call to be his best man. So with the support of his new fiancé Zooey, (portrayed by Rashida Jones) Peter arranges a bunch of man dates with some extra help from his family. After a string of disastrous encounters, Peter meets Sidney Fife, (played by Jason Segel) and the two become quick friends. But their blooming “bro-mance” starts to push Zooey out of the picture.
Why he’ll love it: Rudd and Segal have worked together before and their chemistry shows. There’s no shortage of physical comedy to accompany a very punchy script. The movie includes cameos from Andy Samberg, J.K. Simmons, and Jon Favreau.
Why she’ll love it: We’re really just looking for 2 people falling in love. We’re not going to discriminate!
8. The Princess Bride
An epic rom-com list that doesn’t include The Princess Bride? INCONCEIVABLE! This oldie may have been originally released 1987, but I assure you it is without a doubt one of the best films to recommend for a date night with your modern day ladylove. The scene is set like classic fairy-tale story, “about the most beautiful woman in the world, the hero who loves her, and the evil prince who says he wants to marry her.” The film stars Cary Elwes as Westley, Robin Wright as Princess Buttercup, and was directed by Rob Reiner, who is no stranger to this genre as the director of When Harry Met Sally.
Why he’ll love it: “Hello. My name is Inigo Montoya. You killed my father. Prepare to die.”
Why she’ll love it: This movie is the premise of Disney Princess films, just all grown up. It’s a classic love triangle, with men who are willing to duel for a woman’s hand. Just make sure she has space to swoon. Extra brownie points if you can find it playing at an outdoor theater in your area this summer!
7. My Big Fat Greek Wedding
Meeting the parents can be tough. When the woman you’re dating is Greek, meeting her parents means meeting her whole family. Toula Portokalos (played by Nia Vardalos) finds the man of her dreams Ian Miller (John Corbett), but it’ll take a lot of work for Toula’s family to accept she’s marrying a non-Greek. Especially considering her father Gus thinks, “There are two kinds of people – Greeks, and everyone else who wish they was Greek.” From stereotypically accurate jokes about Greek pride, to cameos from N’SYNC’s Joey Fatone, this film is laugh out loud funny.
Why he’ll love it: You’ll be able to laugh knowing you will never have to meet a family like this one. Unless of course, you’re dating a Greek woman (sorry, sweetheart!), then you’ve been fairly warned.
Why she’ll love it: Star-crossed lovers meet by chance. Her family doesn’t approve. *SPOILER ALERT* He goes as far as converting to the Orthodox faith so they can get married in her family’s church. If that’s not commitment, I’m not sure what is.
6. Forgetting Sarah Marshall
Breaking up is hard to do. When it’s your long-term partner of 5 years, who you live and work with that’s traumatic. For Peter Bretter’s situation you would have to come up with a whole new word, because his now ex-girlfriend is also the incredibly gorgeous, super famous, Sarah Marshall (played by Kristen Bell). Trying to deal with his heartache, Bretter (portrayed by Jason Segel) hops a plane to Hawaii. To make matters even worse for poor Peter, he winds up at the same hotel as his ex beau, who’s brought along her new boyfriend: An eccentric former heroine addict, turned rocker played by Russell Brand. Peter bands together with staff and guests from the hotel to try and mend his broken heart, and once and for all, forget the famous Sarah Marshall.
Why he’ll love it: The script is written by Jason Segel, and boasts a very large, and very well known supporting cast including but not limited to Paul Rudd, Mila Kunis, Bill Hader, and Jonah Hill, who are all full of ideas to help Peter move on.
Why she’ll love it: We’ve finally been given a reason to hate on the otherwise completely perfect Kristen Bell for 2 hours.
5. 10 Things I Hate About You
As a late 90s classic, 10 Things I Hate About You is a must see! We meet Cameron Jones (played by Joseph Gordon-Levitt) on his first day at Padua High School. Of course as it always goes, while touring the school he spots his dream girl Bianca Stratford (played by Larisa Oleynik). But there’s a problem. Bianca isn’t allowed to date until her older sister Kat (played by Julia Stiles) starts dating. So all Cameron needs to do is find a guy willing to date Kat, which trust me is going to be quite the challenge. This can’t go wrong can it?
Why he’ll love it: With major appearances by Heath Ledger and Allison Janney, this film takes funny to the next level. Plus the added relatability of the insanely awkward experience that is high school makes for some amazing fodder. I mean “It’s not everyday you find a girl who’ll flash someone to get you out of detention.”
Why she’ll love it: Larry Miller does an outstanding job helping bring Bianca and Kat’s father to life. He is the perfect summation of every fearful father, whose little girls are all grown up.
4. My Best Friend’s Wedding
Hell hath no fury like a woman scorned. Don’t let the title fool you; this is not a joyous occasion. Well, not for Julianne Potter anyways. Years ago, she made a pact with her long-time college friend Michael O’Neal (played by 90s dreamboat Dermot Mulroney): if neither of them had settled down by the time they turn 28, they’ll marry each other. With her birthday around the corner, Potter, played by a MUCH younger Julia Roberts, is literally knocked over by the news that Michael is getting married… IN 4 DAYS! You know when it’s a bad time to realize you’re in love with someone? Probably when they call to ask you to talk them out of bailing on their wedding. Roberts decides to head to Chicago to help… Break up the happy couple that is.
Why he’ll love it: Mulroney’s love interest just happens to be a very young Cameron Diaz, so even if you can’t fall in love with the script (which you will because it’s hilarious), you’ve got some beautiful people to look at. Plus, for once it’s 2 women fighting over 1 guy. I don’t know many men that wouldn’t enjoy some version of that.
Why she’ll love it: Julia Roberts graciously brings to life the ‘Crazy Ex-Whatever’ in us all. Plus it has one of the most wonderfully choreographed lunch scenes in all of cinematic history.
3. 50 First Dates
There was once a time when Adam Sandler was funny. I swear this time existed! It was also a time before Will Smith started relentlessly pushing his kids on us, it was a truly a simpler time. The year was 2004, and Sandler teamed up for the second time with Drew Barrymore to bring us rom-com gold in the form of 50 First Dates. We meet island playboy Henry Roth (Sandler) who in his travels from bed to bed, stumbles across Lucy Whitmore (Barrymore), a beautiful artist who is quick to fall under Roth’s spell. But the joke’s on him. Lucy suffers from short-term memory loss, and her memory “resets” every night when she falls asleep.
Why he’ll love it: Sandler’s raunchy humour is coupled with hilarious physical comedy, some of which may or may not involve a walrus. Just sayin’. The movie also sees cameos from Maya Rudolph and Dan Aykroyd. Like I said, it was a simpler time.
Why she’ll love it: The premise of this movie is a man who goes to extensive lengths each and every day to make a woman fall in love with him all over again. Need I say more?
2. Notting Hill
Any 90s girl will tell you that no rom-com list is ever going to be complete without the inclusion of something Hugh Grant. If scientists somewhere could weaponize charming mystification, Mr. Grant would be a killing machine. In 1999, he paired with Julia Roberts for the film Notting Hill. Roberts portrays the role of an American Actress, Anna Scott, while Grant plays William Thacker, an introverted London bookstore owner. Their chance meeting over spilled orange juice turns into a quick kiss, which blossoms into one of the greatest love stories ever told (and that’s my completely unbiased opinion, of course).
Why he’ll love it: For once, Hugh Grant is anything but his usual suave self in this film. He’s a socially awkward, glasses wearing, “whoopsie-daisy” saying, regular old guy. And for once, he might finally be the one getting screwed over.
Why she’ll love it: “I’m also just a girl, standing in front of a boy, asking him to love her.”
I’m sure there are raised eyebrows at this one, but hear me out. Yes, on the surface it may seem like just another super hero movie, but anyone who knows the origin story knows that Wade Wilson (brought to life by Ryan Reynolds) was diagnosed with a rare form of cancer. He is abducted and is subjected to a rogue experiment that leaves him with accelerated healing powers, but ironically badly scarred. He spends the movie trying to hunt down the man responsible for the experiment so he can have it reversed, and return to his ladylove Vanessa, portrayed by Morena Baccarin. The R rating on this movie left a lot of room for the writing team to keep the jokes, and the violence, coming from the second the film starts.
Why he’ll love it: This might be one of the only films where Ryan Reynolds is not clearly the major heartthrob, and he holds no punches when making himself the center of that joke. As the first R-rated super hero film, Deadpool also brings adrenaline rushing, sitting on the edge of your seat action. Not to mention the rating allows us to visit Wade’s love interest Baccarin at the strip club she works at. Do I really need to keep selling you on this one?
Why she’ll love it: There are rumours floating around the Internet that Mr. Reynolds does a little full frontal. (So at least the nudity goes both ways).
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