Instead of yet another “Best Romantic Comedies” list that inevitably ends up with When Harry Met Sally (no doubt a fantastic film), let us instead shine a new light on the supporting characters and second fiddles in those films who are ultimately passed over in favour of the hero.
Not everyone can be Tom Hanks or Meg Ryan, and if we’ve learned anything this century, it’s that despite the number of times you take off your shirt in the pouring rain to impress your crush, she’ll ultimately end up with your vampire rival and relegate you to pseudo-godfather status after imprinting heir supernatural baby. We’ve all been there, right? This celebratory collection of romantic outcasts and second fiddles includes some cheaters, best friends, or those just guilty of not making the lead character happy, but for all their faults (or lack thereof) they really wouldn’t be the worst dates to share Valentine’s Day with and could use a little recognition.
#10
Character: Andrew Hennings
Film: Sweet Home Alabama (2002)
Actor: Patrick Dempsey
Does the perfect marriage proposal exist? According to fans of this film, being instructed to “pick one” inside Tiffany & Co. while your partner professes his love is right up there. Charming, self-assured, and generous, Andrew’s shining moment comes when he doubles down on his love for Melanie (Reese Witherspoon) even after she confesses that she’s still married to her childhood sweetheart Jake (Josh Lucas) whose love for her was literally (with lightning) written in the sand. Yes, Andrew’s overbearing and demanding mother would be a lot to deal with, and yes, Jake is equally kind and charming, but you have to hand it to Andrew for his decisiveness.
How Things Ended
After Melanie and Jake have a quotably cute reunion in the rain, they return to her and Andrew’s failed wedding reception and dance together on his dime. The end credits do say he gets engaged but something tells us he also has a bright future in medicine.
#9
Character: Julianne “Jules” Potter
Film: My Best Friend’s Wedding (1997)
Actress: Julia Roberts
Inspiring countless wedding parties to sing “I Say a Little Prayer” in the middle of brunch, this box-office hit sees America’s Sweetheart in an unfamiliar role, the second choice, desperately trying to manipulate and sabotage the nuptials of her friend Michael (Dermot Mulroney) who she now realises she loves. In fact, they did promise to marry each other if they were single at the ripe old age of 28, but in her way is Kimmy (Cameron Diaz), Michael’s perfect fiancé, who, despite not even being old enough to drink at her own wedding, truly loves Michael. After being confronted in a public bathroom (as you do) Jules finally apologises and concedes.
How Things Ended
After giving the maid of honour speech at the wedding, Jules’ friend George (the always delightful Rupert Everett) comes to support her and they dance the night away.
#8
Characters: Lon Hammond, Jr., Richard White, Prince Edward
Films: The Notebook (2004), Superman Returns (2006), Enchanted (2007)
Actor: James Marsden
Poor James Marsden. Always a groomsman and never the groom, except fittingly, in 27 Dresses, Marsden’s sweet and safe demeanor are a blessing until his leading ladies inevitably leave him. You have to hand it to him though, if you’re going to be optimistic about gracefully losing your sweetheart over and over, it might as well be to Ryan Gosling and Superman.
How Things Ended
Apparently he didn’t write enough letters or look good enough in the rain, and then there’s the thing about not being the strongest superhero of all time, BUT, he does find happiness with icon Idina Menzel in Enchanted and they live happily and cartoonishly ever after.
#7
Character: Riley Bennett
Film: Happiest Season (2020)
Actress: Aubrey Plaza
In a supporting role that took social media by storm, Riley was the emotionally mature and witty ex-girlfriend of main character Harper (Mackenzie Davis) in Clea Duvall’s hilarious holiday film. Viewers noted, however, the undeniable chemistry and on-point blazer game between Riley and Abby (Kristen Stewart) Harper’s girlfriend, and debated whether they would have been a much better fit, seeing as how Harper underappreciated Abby. This second fiddle is not as much a second choice or one that got away, but perhaps, one that should have happened.
How Things Ended
Harper apologizes to Riley for the way their relationship ended and with a handshake, closure is reached. She gives her stamp of approval on Abby, and gracefully exits the film. We’ll hold out hope for a sequel following the adventures of Riley and John (Dan Levy).
#6
Character: Daniel Cleaver
Film: Bridget Jones Diary (2001)
Actor: Hugh Grant
Daniel Cleaver already has two strikes against him. He’s the boss of Bridget Jones (Renée Zellweger) and uses that power (along with his charming pitter-patter) to his advantage but after they start dating, his second strike of being a notorious womanizer ruins things when Bridget finds him with a naked Yankee in his flat. Despite poor attempts to make things right, Bridget refocuses her affection on Mark Darcy (Colin Firth) the reserved barrister with a romantic soul.
How Things Ended
Daniel and Darcy have fisticuffs in the snow (born out of Daniel sleeping with his wife) but Darcy gets the best of him and reunites with Bridget in a public snowy embrace full of onlookers marveling at her animal print underwear.
#5
Character: Jordan Armstrong
Film: The Best Man (1999)
Actress: Nia Long
Jordan has been drinking tequila, her hormones are out of control, she’s emotional, horny, and doesn’t want to hear anything about peas! Shame on Harper (Taye Diggs), who has a girlfriend, for leading her on and getting angry about airing his own dirty laundry that he decided to write about! She’s a strong, confident woman, who just wants honest companionship and Harper learns quickly that she’ll slap the soul out of you if you wrong her.
How Things Ended
After getting closure with Harper, Jordan takes the high road and tells him that Robyn (Sanaa Lathan) is the woman for him. Harper proposes to Robyn on the spot in front of the whole wedding (taboo!) and all is right in the world as everyone does the electric slide.
#4
Character: Julian Mercer
Films: Something’s Gotta Give (2003)
Actor: Keanu Reeves
Keanu Reeves needs no explanation as to why he’s an eligible bachelor but his character Julian, a sensitive, and caring doctor, may take the cake. He’s utterly infatuated with Erica Barry (Diane Keaton) and deserved so much more than being left for the man who owns the heart he heroically saved. However, if we’re being honest, he’ll do just fine showering someone else with affection because he’s Keanu, and looks immaculate in a turtleneck.
How Things Ended
Julian graciously steps aside for Erica to be with reformed womanizer Harry (Jack Nicholson) in a move elevating him to romantic saint status. There are worse places to be left than Paris. Who knows, maybe he’ll find love in the time portal from Midnight in Paris.
#3
Character: Fiona
Film: Four Weddings and a Funeral (1994)
Actress: Kristin Scott Thomas
When it comes to romance, nothing is quite as painful as unrequited love. We can all empathize with Fiona, the beautiful and witty friend of Charlie (Hugh Grant) who has loved him since the day they first met but her feelings aren’t reciprocated. Fiona’s tender confession to Charlie (brilliantly played by Kristin Scott Thomas) still breaks hearts to this day. Such is life.
How Things Ended
Charlie leaves his own bride-to-be at the altar for young American Carrie (Andie MacDowell) who he just can’t seem to shake. As for Fiona, the end of the film shows her with Prince Charles, who frankly, doesn’t deserve her.
#2
Character: Walter Jackson
Film: Sleepless in Seattle (1993)
Actor: Bill Pullman
Apparently being a nice (albeit, slightly dull) man in the early nineties was considered a fatal flaw. Walter loves Annie (Meg Ryan) who in turn is infatuated with Sam (Tom Hanks) who she’s only heard and never met. Sure, Walter has a lot of allergies, and yes, maybe he can’t dance, but he’s sweet, has a cute sense of humor (to everyone but Annie’s family), and above all else, is devoted to Annie and gives her the space she needs…which, in the end, backfires on him. His character is the epitome of a nice guy who finishes last but deserves some love of his own.
How Things Ended
Annie tells Walter that she doesn’t deserve him as she dumps him on Valentine’s Day at the Rainbow Room. Actor Bill Pullman, however, got the best of Tom Hanks a year earlier in A League of Their Own, so the universe balances itself.
Honorable Mentions
Michael Grates (Ben Stiller) – Reality Bites (1994)
Halley Buchanan (Bridget Moynahan) – Serendipity (2001)
Ethan (John Krasinski) – Something Borrowed (2011)
Palmer Dodge (Brooklyn Decker) – Just Go With It (2011)
Keanu Reeves (Keanu Reeves) – Always Be My Maybe (2019)
Gertrude (Malin Akerman) – The Proposal (2009)
Johnny Cammareri (Danny Aiello) – Moonstruck (1987)
Adriana (Marion Cotillard) – Midnight in Paris (2011)
Karl (Rodrigo Santoro) – Love Actually (2003)
#1
Character: Phil “Duckie” Dale
Film: Pretty in Pink (1986)
Actor: Jon Cryer
This list couldn’t possibly exist without including perhaps the most famous friend-zoned character of all time. We fell in love with Duckie at a record store as he lip-synched an Otis Redding tune but unfortunately, test audiences didn’t love him quite enough. In the original ending to the film Duckie does end up with Andie (Molly Ringwald) but that result was loudly booed at test screenings and eventually was reshot to find Duckie encouraging Andie to go after Blane (Andrew McCarthy) the popular kid he conceded was not like the others.
How Things Ended
Duckie locks eyes with a young Kristy Swanson credited as Duckette (yes, that’s real), and performs the dependable John Hughes trademark of breaking the fourth wall as OMD’s classic “If You Leave” plays in the background. Ah, the eighties. What a time.
If you’re feeling the pain of the second fiddles, check out these Valentine’s Day flicks if you’re down and out on love.
