Romantic Comedies – Which Couples Would Have Made the Distance?

June 1, 2020
Elle Magazine recently published a list of the top 20 romantic comedies of all time and in the interests of pointlessness, Stephen Vagg thought that he would offer his ten cents’ worth of opinion on whether the lead characters would get together for life.

Open the conversation to screenwriter friends ( Louise Alston (LA), Holly Lyons (HL), Michaeley O’Brien (MO), Jessie Marshall (JM) and Alexa Moses (AM), plus not-a-screenwriter-but-watched-a-lot-of-rom-coms Leith Sutherland (LS). Thanks to all for contributing.), they came up with differing opinions on this much loved/much maligned film genre where everyone lives happily ever after… or do they?

Stars’ names are used instead of character names because, honestly, who cares about character names in a rom com? Oh and PS (SPOILERS) for the films, but seriously…

Heath Ledger and Julia Stiles in 10 Things I Hate About You (1999)

SV: Can’t see these two lasting beyond college but I don’t think that either would feel bad about that fact.

AM: How is 10 Things I Hate About You number 1 on the Elle list???

SV: Maybe the age of the writer, I don’t know.

Alicia Silverstone and Paul Rudd in Clueless (1995)

SV: I actually really, really hope these two would stay together… I feel maybe they would break up for a few years due to some big thing (eg. he starts work) but then reunite. She won’t want to live on the salary of an environmental lawyer, but a trust fund from dad could sort out that problem.

JM: As much as I love Clueless, I will always slightly be creeped out by the ending.

Meg Ryan and Tom Hanks in You’ve Got Mail (1998)

SV: Yes, absolutely, they’d still be together. Not sure how they’ll be doing financially in this Amazon age, but still together.

JM: Kathleen Kelly (Meg) would not only be a famous children’s book author by now, but she would have been snapped up by Vulture or Huffpo and be writing beautiful and thoughtful pieces on life in New York, and have captured a large demographic of women young and old who follow her pieces religiously. She would be, in other words, Nora Ephron. Joe (Tom) would have gone bust of course but has now pivoted to the audio sphere and is producing podcasts and audiobooks – although he doesn’t quite get the appeal. They would absolutely still be living in her little brownstone. She would have made him sell the damn boat. They spend enough time with the right people that Joe knows how to be “woke” but he secretly resents her success when he can’t sleep in the middle of the night, but he really loves her so he’ll never say anything. He’ll just let it turn into stomach cancer and die before her, so she can write glorious pieces on grief and heartache which will only catapult her further. But he really does love her…

Cary Grant and Rosalind Russell in His Girl Friday (1940)

SV: The two lead characters would have repeated the plot of the film about three more times before one dies of lung cancer/heart attack/in the war/something.

Andie McDowall and Hugh Grant in Four Weddings and a Funeral (1994)

SV: Nope. Wouldn’t last ten years. Charles (Hugh) would still be close to all his mates though, which is the real romance of that film. (Maybe he and Fi?)

LS: Definitely no. She doesn’t like living in the UK, so they move to the USA. After a few years, he realises that he made a big mistake and it’s all over, but they have kids. And how does he leave the kids? The love slowly dies. He misses his old life and friends. Blames her. Totally acrimonious.

LA: He goes home, divorced to find half his friends aren’t speaking to the other half because they voted leave… he wonders why all his friends in the ‘90s were white. Then he realises he, they and the whole UK jumped the shark in 2000.

Shirley MacLaine and Jack Lemmon in The Apartment (1960)

SV: Unqualified yes!

Sandra Bullock and Bill Pullman in While You Were Sleeping (1995)

SV: Not sure this film should be on this list but yes.

Tom Hanks and Meg Ryan, again, in Sleepless in Seattle (1993)

SV: Oh c’mon, Meg and Tom, what do you think?

JM: They are absolutely still together and while they never had a child together, Jonah remains the apple of their eye – especially now that he’s turned their story into an award winning film and is now a famous filmmaker living in the Hollywood hills with Jessica (who, like, so totally predicted this would happen, like how totally meta right?)

Diane Keaton and Jack Nicholson in Something’s Gotta Give (2003)

SV: I’ve got a feeling they might mostly stay together because Jack would have a stroke or something… Diane really should have gone for Keanu [who plays the false love interest].

JM: Unquestionably, Jack is dead and naturally she wrote another hit play about the grief of losing him. Keanu turns up to the premiere with his new wife, but incidentally introduces her to one of his hot friends and she goes home with him. This kickstarts the next few years of beautiful NSA sex with a string of younger men.

Julia Roberts and Hugh Grant in Notting Hill (1999)

SV: You know something? I think yes. I really like the coda for that film, I think it was crucial to show how the relationship might actually work on a practical level.

MO: I love this film. I agree with you about the coda.

Piper Perabo and Lena Headey in Imagine Me and You (2006)

SV: Yes!

Kate Hudson and Matthew McConaughey in How to Lose a Guy in Ten Days (2003)

SV: Those actors have really good chemistry. Maybe…

HL: It was true love until he turned gay, so she faked her own death and framed him for it. It’s well established she’s a good liar.

LS: How do they even get together at the end? They don’t know each other at all except that they’re both good looking.

Meg Ryan and Billy Crystal in When Harry Met Sally (1989)

SV: Hmmm… I’d really, really like to think so. I can just see Harry (Billy) straying. Sorry.

AM: You really think Harry would cheat on Sally (Meg)? Gaaaah. You’re making me sad.

MO: Harry’s all talk. Once he’s finished posturing, he’d never cheat on her.
AM: Totally agree. He knows he’s damn lucky to have her.

SV: Ah, he’ll take her for granted in five years and start resenting her in another five…

LA: Harry loooooooooves her!

JM: I want to believe. But I can also just see him snapping one day in a restaurant as she takes a full 8 minutes to order a sandwich and storming out only to be discovered with the waitress out the back.

LA: He LOOOOOVES that. He could never order something that’s not on the menu. By the end of the movie he considers it brave. 🙂

LS: I think she tires of him! Realises her mistake about 5 years later when she meets some incredibly sexy guy…

AM: I don’t think so since he didn’t CHEAT ON HELEN! She left HIM!

HL: Don’t work out coz he just can’t make her come.

SV: True – Harry would be forever paranoid about the authenticity of those orgasms.

HL: As is every bloke who has seen the movie!

Cher and Nicolas Cage in Moonstruck (1987)

SV: You know something? I think yes, they’d make it. It wouldn’t be easy, but they are very Catholic. I do feel Nicolas Cage might kill himself in a kitchen accident with that hand.

Cameron Diaz and Dermot Mulroney in My Best Friend’s Wedding (1997)

SV: Julia Roberts will still be BFF with Rupert Everett. Oh, the other couple…? Yeah, they’ll be fine, provided the guy actually goes to work for Cameron’s dad (she’ll only take a few years of journo poverty). Actually, I like to think Julia would have had Rupert’s baby and that kid would romance Cam and Dermot’s kid.

Julia Roberts and Richard Gere in Pretty Woman (1990)

SV: I think they’ll be fine, he’ll be too busy working to cheat and she’ll have plenty of money to buy things. And these two do have nice chemistry.

HL: She gives him a crippling STD that he tragically dies from.

MO: I remember there was speculation for years about a sequel. He was going to be a Senator. She the wife. Someone would expose her past. Eventually they gave up and made Runaway Bride. That’s in my top five.

AM: Yes where is Runaway Bride?

SV: Jeez, we’re flushing out all the Runaway Bride fans with this one…

Parminder Nagra and Jonathan Rhys Meyers in Bend It Like Beckham (2003)

SV: Please. She couldn’t get on that plane fast enough.

LA: Those girls will eventually come home with gold medals and wedding rings…. to each other.

Too many to list in Love, Actually (2003)

SV: Tough one. Hugh and Martine, sure. Alan and Emma, yes, they’ll plod along. The two stand ins, yes. Colin and his girl – no, not once they start speaking each other’s language. Keira and her guy… they didn’t really have characters, I can’t tell. Liam and Claudia Schiffer – sure. I really really hope Laura Linney finds happiness.

JM: I just want a follow up film that follows Laura Linney, freed by her brother’s death, as she journeys through Europe in a bid to rediscover herself. Which of course is just a series of montages of her buying cute dresses in tiny seaside op shops, eating ice cream in cobbled streets and of course, sleeping with every single man who crosses her path. All the men look and sound like Karl.

Colin Firth and Renee Zellweger in Bridget Jones’s Diary (2001)

SV: If they haven’t broken up after two sequels they’ll make the distance.

LS: The movie invented the whole baby daddy thing. I don’t like that third movie because it has broken them up – totally ruining the happy ever after! In the books, they are together. She has two kids with him. And then he dies. All before the third book begins. Maybe that movie is yet to come?

SV: They should’ve killed D’Arcy (Firth) for part three – had it about her finding someone new – if they wanted Colin Firth, he could’ve come back as a ghost or something.
LS: At least in the book, they left that romance alive (just with him dead). And then her trying to find romance was the amusing part. I would have been happy for a movie with just Mcdreamy (Patrick Dempsey) and no Colin Firth. Now, who will they get to play the male lead if they make another?

Mark Ruffalo and Jennifer Garner in 13 Going on 30 (2004)

SV: Absolutely still together!

HL: He gets arrested for pedophilia.

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