The Ultimate Guide To The All-Time Best Romance Movies and Rom-Coms By Professional Matchmakers [And Hopeless Romantics]

Best Rom Coms Ever


Just in time for the holidays – i.e: flannel blankets, slippers, hot chocolate and all the warm fuzzies – we present you the definitive top romance flicks as nominated by some of the world’s elite matchmakers and general lovers of love. Here the experts of love depict why these films are the best to cuddle up to this season or to just brighten up your pandemic days with pure romantic indulgence! God knows we could all use as much levity as we can get right now! 


  1. Pretty Woman

Pretty Woman

In this Cinderella tale, respun and far more adult, a prostitute and a wealthy businessman fall for each other in a big and adorable way, forming an unlikely love that traverses class. This film stars Julia Roberts and Richard Gere in their prime (drool); their chemistry is on fire, it’ll sweep you off your feet, and give you allll the 90’s nostalgia. 


  1. Notting Hill

Notting Hill

Starring the royalty of the rom-com genre – Hugh Grant and Julia Roberts – this 1999 classic revolves around a full-blown love affair caused by a serendipitous run-in and spilled orange juice. Is love possible between a bookseller with a humdrum life and a glamorous Hollywood actress? Of course it is in rom-com land! 


  1. Ever After (Lyon’s Elite CEO’s all-time favourite!) 

Ever After

In another adaptation of the Cinderella story, a vivacious young girl named Danielle (Drew Barrymore) is forced into servitude by her evil stepmother (played by the divine Anjelica Houston) and mercilessly taunted by her stepmother’s scrappy spawn of daughters. Danielle throws a rock at a man on a horse who she thought was a trespasser, hits him square in the head, he falls off, she realizes he’s the Royal Prince and…the rest is very juicy history. The best soundtrack, and 100/10. 


  1. The Wedding Singer

The wedding singer

A 10/10 if you’re feeling down and you need a sweet laugh and the movie equivalent of, like, a hug from a golden retriever. Adam Sandler plays the world’s biggest sweetheart weirdo wedding singer who is completely shattered after his fiancee leaves him at the altar. Along comes Julia played by Drew Barrymore who enlists his help for her upcoming wedding with a real scumbag. Feelings are felt! There are major misunderstandings! Will true love reign? Yes! 


  1. The Notebook

The notebook

Rated 14/10 hot, hot flames…two words: Ryan Gosling. Ryan Gosling is often topless. Where was I – oh yes – set in 1040’s south Carolina, a teenage millworker named Noah falls in love at first sight with rich socialite Allie. Noah goes to war, Allie’s evil mom hides the letters he wrote her every day, he shows up on the cusp of her wedding with Mr. Rich Guy, and we learn that the romance is anything but over. Has there ever been anyone who has not cried watching this movie? 


  1. Love Actually

Love Actually

A Christmas movie must, this perfectly cast, iconic film follows nine intertwined stories all examining the labyrinthian complexities of love – the ups, the downs, the sideways, the inside outs. It’s perfect. It’s perfect! 


  1. My Best Friend’s Wedding

My best friends wedding

This 1997 Classic stars yet again our patron saint Julia Roberts. Julianne and Michael have been best friends forever and they vowed that if they were still single by 28, they’d marry each other. Lo and behold Michael announces his engagement to a beautiful 20-year-old for days before he turns 28. Of course, Julianne realizes she’s in love with Michael, vows to intercept the wedding until the 20yr old Fiancee of Michael (Cameran Diaz, anybody?) invites her to be the maid of honour. Eek! 


  1. The Holiday

The Holiday

English Iris (Kate Winslet) and Cali-girl Amanda (Cameron Diaz) have both been betrayed by scumbags. Meeting over a housing swap website, they befriend each other and agree to swap over Christmas. Hilarity ensues and both of their broken hearts receive some…unexpected pleasures. Yum! 


  1. To All The Boys I’ve Loved Before

To All The Boys I've Loved Before

Oh, the traumaramas of high school! Based on a bestselling Young Adult novel by Jenny Han, this 2014 movie follows high schooler Lara who deals with her intense feelings by writing long love letters to her crushes and locks them away in her closet. One night her rascally younger sister discovers them, mails them to the boys (!) and all havoc breaks loose for Lara. Poor girl gets trapped in more of a love octagon than a mere love triangle! 


  1. You’ve Got Mail

You've Got Mail

First of all, this will make everyone who witnessed the 90’s very nostalgic for the internet’s early days. Second – what is it with rom-coms and bookstores? Anyway, another watch-one-hundred-time classic, Meg Ryan plays a struggling independent bookstore owner and Tom Hanks plays the owner of the corporate book chain that recently opened up nearby and puts Meg’s store out of business. Little do they know they have been falling in love in an anonymous online chat room. When Hanks’ character realizes this…boy’s gotta jump more than a few hoops. 


  1. Just Friends

Just Friends

If you’re in the mood for some serious slapstick comedy, this rom-com is for you. Ryan Reynolds plays nerdy, pudgy Chris, who in high school is desperately in love with his best friend Jamie (Amy Smart) and she friend zones him hard. Ten years later Chris is a successful record label exec who has clearly adhered to a fitness plan. When a vacation to Paris falls through, he and his hilariously self-absorbed pop star girlfriend go to his hometown instead where he tries yet again to win back Jamie who his heart still burns for. 

  1. Silver Linings Playbook


Silver Linings Playbook

A rom-com that focuses on mental illness! More of this, please. Pat (played by Bradley Cooper) has lost his wife and kids due to his unmanaged manic behaviour due to his bipolar disorder. After leaving a mental institution and having to live with his (hilarious) parents, Chris is obsessed with getting himself and his life together enough to win back his life. He meets a family friend named Tiffany who struggles with serious depression after her husband’s death. Tiffany agrees to help him reconnect with his wife as long as he promises to do one special thing for her…

  1. Never Been Kissed

Never Been Kissed

In this ‘99 classic, Josi (played by queen of sweetness Drew Barrymore) is a junior copywriter at the local paper. She goes undercover at her former high school to investigate current teen culture for an article, successfully infiltrates the popular clique (she was a hopeless nerd in her own highschool experience), has to confront her own failed love life, and when she falls for the hot English teacher, not blowing her cover is proving especially difficult. 


  1. Me Before You 

Me Before You

A very quirky Louisa (played by Emilia Clark) takes on one of many jobs she cycles through to try to help her family make ends meet. Completely inexperienced but determined to learn, she works as a caretaker for – an of course dazzlingly handsome – young banker who was recently paralyzed in an accident. His deeply depressed cynicism seems permanent but things begin to change in a – you guessed it – magical romance way. 

  1. 10 Things I Hate About You

10 Things I Hate About You

Beautiful, smart, angsty, Kat (played by Julia Stiles) rubs her classmates, especially the boys, the wrong way and this self-possessed teen doesn’t even pretend she likes them. Unfortunately for her younger sister, she can’t date until Kat does (her parents full-well knowing that is unlikely to happen). Strings are pulled, a new boy arrives on the scene who may just be The One, that is if stubborn Kat lets her guards down. 


  1. While You Were Sleeping

While You Were Sleeping

A very lonely tollbooth worker (played by Sandra Bullock) is desperately in love with a man who has no idea she exists even though he buys a ticket from her at the same time every morning. One morning he gets shoved onto the tracks, she saves him from an oncoming train, he’s in a coma, his family misunderstands him to be his fiancee, and heartwarming hilarity ensues. 

  1. The Princess Bride

The Princess Bride

A cult classic and an absolute timeless gem for good reason, this classic fairytale comes with plenty of twisted humour and breathless romance. Priceless one-liners all the way through – “inconceivable!”

  1. Say Anything 

Say Anything

In this 1989 gem (remember landlines?!?) about first love, John Cusack plays Lloyd – a dreamer deadset of winning the heart of the picture-perfect, straight-A student Diane. To everyone’s shock, turns out she has a soft spot for the bumbling sweetheart even though she’s way out of his league. Understandably enough, Diane’s overprotective father proves a huge challenge – but for Diane, Lloyd will literally do anything or say anything. 

  1. Bridget Jones

Bridget Jones

For a new year’s resolution, 32-year-old Bridget decides it’s time to completely transform herself and her life. First step? Start keeping a diary to record everything. Witty, opinionated, a magnet to embarrassing herself she writes it all. She’s got a lot to say about men, food, sex and every other troublesome facet of life. 

  1. When Harry Met Sally

When Harry Met Sally

The age-old debate: can men and women ever (truly) be platonic friends? Famous for “the diner scene” (if you know you know), some call this the #1 rom-com of all time. College graduates Harry (Billy Crystal) and Sally (Meg Ryan) argue in a car about whether platonic friendship is possible between a straight male and female; ten years later the debate and attempt to stay friends without sex getting in the way…hilariously fails. 

  1. Long Shot

Long Shot

Delightfully unexpected amazing chemistry between Seth Rogan and Charlize Theron in this hilarious rom-com. Fred Flarsky is a rabble-rousing and outspoken and eccentric journalist, Charlotte Field is a politician – smart, accomplished, and internationally popular. When they run into each other, they realize Charlotte was once Fred’s babysitter (and massive childhood crush). Charlotte runs for the presidency, hires Fred as her speechwriter despite protests from her colleagues and…watch it!

  1. 13 Going On 30

13 going on 30

As lighthearted as it gets, this silly fairytale will bring you right back to being thirteen. Jenna wants boobs, she wants a boyfriend and she dreams of being a well-adjusted woman rather than stuck in the purgatory of her early teens. Insert some fairy dust, and BAM she wakes up as a 30-year-old (played by Jennifer Garner). Hilarity and sweetness ensue. 

  1. 50 First Dates

50 first dates

Another Adam Sandler + Drew Barrymore romantic comedy – candy for the soul! In this one, Lucy has a form of short term memory loss wherein she can’t remember anything that happened the day before. Henry, a veterinarian and consummate player falls seriously for Lucy (very unlike him) and finds a way to woo her every day. Her friends and family are doubtful of this playboy’s intentions, so he’s got to be very creative. Pure joy, this one. 

  1. Dan In Real Life

Dan In Real Life

Another bookstore as the setting for burgeoning l-o-v-e! But of course, there are problems. Widower Dan (Steve Carell) is a beloved advice columnist, and father of three girls. After arriving at his parents’ for a family get together, he takes refuge for a breather at a local bookstore where he meets and falls for Marie (Juliette Binoche). But – there’s always a but – turns out Marie is the new girlfriend of Dan’s brother. 11/10 for heartwarming middle-aged, feel good, aw-shucks, romance.


  1. Hitch 


Will Smith plays Alex “Hitch” Hitchens, a dating coach who mentors clueless men on how to…not be dufuses in love and he does an excellent job at it. While working with one particular bumbling client his techniques are going well, but when he tries to use his own techniques on a tabloid reporter and they fail, things get complicated. That’s just the main plot – the subplots are juicy and altogether very fun. 

  1. How to Lose a Guy in 10 Days

How to Lose a Guy in 10 Days

Andie (played by Kate Hudson) is a Carrie Bradshaw type, is an advice columnist pushing the envelope with an article called “How to Lose a Guy in Ten Days.” Her editor urges her to find a man asap to use as a guinea pig for her (hilarious) technique. Enter Ben Berry (played by Mathew McConaughey), who believes he can make any woman fall in love with him. His friends bet him to prove it at a bar, they pick the girl who happens to be Andie and voila – we’ve got ourselves a perfect rom-com. 


  1. Crazy Stupid Love

crazy stupid love

Cal Weaver (played by Steve Carell) has it all – a great job, a beautiful house, wife Emily (played by Julianne Moore) and kids. Learning about his wife’s affair, suddenly Cal is over 40 and single. Not exactly “on his game” dating wise, he befriends ladies man Jacob Palmer (Ryan Gosling) who helps him win the ladies. But what if the player actually falls in love? What if Cal and Emily are soulmates after all? What if??


  1. He’s Just Not That into You

He's Just Not That into You

Ah, a tale most of us know too well about all the frustrations of modern romance. This all-star cast (Jenn Aniston, Ben Affleck, Scarlett Johansson, Drew Barrymore and more!) play a group of interconnected friends in their 20’s and 30’s all trying to navigate the nitty gritty of relationships: ghosting, non-commitment, trust issues, the whole shebang. Deeply relatable. 

  1. Bridesmaids


Destined to be a classic, we dare you not to laugh no matter how many times you’ve seen it. We’ll sum this description up with: “food poisoning scene.” 

  1. PS I Love You 

PS I Love You

Holly Kennedy (played by Hilary Swank) loses her husband and love of her life to cancer. Her late husband, however, planned ahead before he died and arranged for a series of letters to be sent to her beginning on her 30th birthday designed to ease her grief and help her fully enjoy her life. This might sound like a tear-jerker, but it is still really funny! 


So there you have it! Believe it or not, we could have made this list longer, but we kept it to our top thirty. We hope it lets some lightness and warmth into your upcoming winter! 


Best Rom Coms Ever

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