Your Favorite 15 Romantic Comedy Couples & What They'd Be Up to Today

Rob Reiner's 1989 romantic comedy classic When Harry Met Sally spawned the question that's still debated today: "Can men and women just be friends?" And while there have been thousands of think pieces on the subject over the past 25 years, there's an even more pressing question from the classic we all need answered much more: "Are Harry and Sally still together?" Has their decades-spanning courtship of enemies-turned-friends-turned-lovers, which became the foundation for every rom-com until the end of time, still going strong? Or did Sally's long-winded orders go from charming to grating for Harry, and did Harry's karaoke machine phone messages start to push Sally's buttons over time? Well, rest easy WHMS enthusiasts because Sally Albright herself, Meg Ryan, thinks they are doing just fine.

According to Variety, on Monday night Ryan reunited with her co-star Billy Crystal at New York City's Avery Fisher Hall to celebrate Reiner receiving the Film Society of Lincoln Center’s 41st Chaplin Award. Crystal joked on stage, "For those of you who have waited 25 years for a (When Harry Met Sally) sequel, this is it."

So if there was a sequel, would Harry and Sally be together in it? Ryan stated, "Sometimes people want to know what happened to Harry and Sally and I think they are OK."

Phew! We always hoped those two would make it, despite the odds of living in an absolutely picturesque New York City. So now that we know that Harry and Sally are doing "okay" what about some of our other favorite rom-com couples?

We dissect 15 movie couples from the past 25 years.

Image: Columbia Pictures

'When Harry Met Sally'

The Couple: Eternal pessimist Harry Burns (Billy Crystal) meets quirky optimist Sally Albright (Meg Ryan) in college and it’s… hate at first sight. He believes men and women can’t be friends because sex always gets in the way, but she refuses to believe that’s true and the two go their separate ways. But over the course of years living in New York City the two forge an unbreakable bond that eventually turns into love.

Odds of Survival: We’re with Meg Ryan on this one, we think Harry and Sally would still be going strong all these years later. Unlike couples who start with all passion and no real structure, theirs built over time thanks to their admiration for one another. Best friends make the best, most long-lasting couples, in marriage or otherwise. These two are the real article.

Image: Columbia Pictures

'You've Got Mail'

The Couple: Charming, but deceitful chain bookstore owner Joe F-o-x (Tom Hanks) woos his real-life foe, a whimsical independent bookstore owner named Kathleen Kelly (Meg Ryan, again) on the Internet.

Odds of Survival: Considering this was a relationship built completely on deception and lies and he closed her beloved family business, we’re guessing these two went extinct around the same time AOL emailing did.

Image: Warner Bros.

'Love, Actually'

The Couple: Okay, we could do an entire gallery of the Love, Actually couples, so let’s just narrow this down to the heartbroken writer Jamie (Colin Firth) and the beautiful housekeeper he falls for, Aurelia (Lucia Moniz).

Odds of Survival: Pretty slim given the language barriers and that they know next to nothing about each other. Our money would be on the Prime Minister (Hugh Grant) and Natalie (Martine McCutcheon) making a real go of it.

Image: Universal Pictures

'Pretty Woman'

The couple: Successful, but emotionally cut-off businessman Edward Lewis (Richard Gere) picks up a beautiful, delightful prostitute named Vivian Ward (Julia Roberts) and hires her as a companion for a week. They, of course, fall madly in love.

Odds of Survival: Look, love can overcome anything, including prior professions, but when you come from such entirely different worlds, that’s a barrier that even shopping sprees and nights at the opera would have trouble overcoming.

Image: Touchstone Pictures

'While You Were Sleeping'

The Couple: Lonely Chicago train token collector (Sandra Bullock) falls in love with handsome commuter Peter Callaghan (Peter Gallagher) from afar, and then saves his life when he gets pushed on to the tracks. After a mix-up, she’s mistaken for his fiance and his wacky family takes her in as their own while Peter’s in a coma. During that time Peter’s brother, a sweet furniture designer named Jack Callaghan (Bill Pullman) falls for her and romantic entanglements ensue.

Odds of Survival: Never mind that Lucy was in love with his brother first and almost went through with marrying him, but when they were falling in love she never once mentioned the whole not-really-his-fiance thing. Not exactly a foundation of trust there.

Image: Buena Vista Pictures

'How to Lose a Guy in 10 Days'

The Couple: Terrible person/advertising executive Benjamin Barry (Matthew McConaughey) and terrible person/magazine writer Andie Anderson (Kate Hudson) try to con each other into falling in and out of love, respectively, as crude business ventures. Wouldn’t you know it…they fall in love for real despite deceiving their intentions towards each other from the start and acting like lunatics?

Odds of Survival: For the sake of humanity, let’s hope these two broke up 10 days after their “happy ending.”

Image: Paramount Pictures

'The Wedding Singer'

The Couple: Goofy, but sweet wedding singer Robbie Hart (Adam Sandler) gets his heart broken, but finds love again when he meets a lovely, but engaged-to-a-jerk waitress Julia Sullivan (Drew Barrymore). Julia eventually dumps her chump fiance, and thanks to a little help from Billy Idol, gets with her true love Robbie.

Odds of Survival: This couple would last through the ’80s, ’90s, and beyond. Theirs was a love for all the ages.

Image: New Line Cinema

'Say Anything...'

The Couple: Hopeless romantic and kickboxer Lloyd Dobler (John Cusack) eventually wins over the heart of gorgeous school valedictorian Diane Court (Ione Skye), despite her father’s objections. It’s amazing how far a little Peter Gabriel and a boom box can go.

Odds of Survival: Unlike a lot of teen couples, Lloyd and Diane had to endure some actually difficult circumstances. The fact that they made it through (and that Lloyd helped Diane get through some pretty hard times) means they are built to last.

Image: 20th Century Fox

'Notting Hill'

The couple: A-list American movie star Anna Scott (Julia Roberts) finds herself in an unexpected romance with charming British independent travel bookstore owner Will Thacker (Hugh Grant). Okay, fine, just a girl standing in front of a boy asking him to love her.

Odds of Survival: We’d like to give them the benefit of the doubt for a Hollywood relationship because he’s not an actor, but we think this probably had the shelf-life of a long-term Hollywood relationship (read: about ten years).

Image: Universal Pictures

'Sleepless in Seattle'

The couple: Radio listener/borderline stalker Annie Reed (Meg Ryan) falls for Sam Baldwin (Tom Hanks), a widower who lives across the country. Annie learns Sam’s story after his son Jonah calls into a talk radio show and, despite being in a relationship herself, goes to meet Sam at the top of the Empire State Building a la An Affair to Remember.

Odds of Survival: Slim, not only because of the whole stalker thing, but because that pesky Jonah would probably drive a wedge between them somehow.

Image: TriStar Pictures

'Never Been Kissed'

The Couple: Newspaper reporter Josie Geller (Drew Barrymore) goes undercover as a high schooler for a story and, having never been in love before (and, y’know, kissed, as the title would let you know) finds herself head over heels for foxy English teacher Sam Coulson (Michael Vartan).

Odds of Survival: Subtracting the creepiness factor that for quite some time Sam though Josie was a high school student, the whole deceiving-the-person-from-the-start about her true identity (a recurring theme in rom-coms) and the added pressure of being her first everything would probably prove to be too much.

Image: 20th Century Fox

'Jerry Maguire'

The Couple: Disgraced sports agent Jerry Maguire (Tom Cruise) falls in love with single mom Dorothy Boyd (Renee Zelweger), and in turn, her adorable son, as he tries to get his career and life back in order.

Odds of Survival: “Hello,” of course these two made it. But honestly, the real couple of Jerry Maguire was Rod (Cuba Gooding, Jr.) and Marcee (Regina King) Tidwell.

Image: TriStar Pictures

'Knocked Up'

The Couple: Stoner slacker Ben Stone (Seth Rogen) has a one-night stand with beautiful E! correspondent Alison Scott (Katherine Heigl), which leads to an unexpected pregnancy. These two polar opposites decide to make a go of it for the kid.

Odds of Survival: No matter what Easter eggs This is 40 gave us, Ben and Alison, despite their best intentions to make their family work, probably weren’t destined to be together. But thanks to support of their respective family and friends we imagine they split, but excel at loving co-parenting.

Image: Universal Pictures

'The Proposal'

The Couple: To avoid getting deported, Type-A book editor Margaret Tate (Sandra Bullock) convinces her assistant Andrew Paxton (Ryan Reynolds) to sham marry her so that she can stay and he can get a promotion at work. You know, how all great romances start.

Odds of Survival: Considering it’s an illegal union, and one that was build on a series of lies (hell, they even lied to Betty White) there’s no way this one makes it past a few months, let alone the Canadian border.

Image: Touchstone Pictures


The Couple: Popular Beverly Hills high school student Cher Horowitz (Alicia Silverstone) figures out she has feelings for her former brainiac stepbrother Josh (Paul Rudd), and he for her.

Odds of Survival: As if! It was bad enough she was only 16-years-old and he was in college, but the fact that their respective parents were married to each other at one point is totally buggin’. Sure, Josh is a total Baldwin and Cher is the ultimate Betty but…that relationship was way existential.

Image: Paramount Pictures