There is no light without the darkness, no happiness without grief, no romance without romcoms where the heroine chooses a terrible man while a better option is both willing and ready. In the spirit of using garbage to recognize beauty, join me on a journey through five romcoms where the heroine chooses the wrong guy and casts a retroactive pall over what could have been a nice story.
RomCom Heroines Editorial
Princess Ann in Roman Holiday (1953)
Premise: Joe Bradley (Gregory Peck) is a roving reporter in need of a scoop. After a zany series of mishaps, he encounters fellow tourist Anya (Audrey Hepburn), leading the duo to strike up a tender flirtation and enjoy one perfect day in Rome. There’s just one problem: Anya is really Princess Ann, who is on the run from her oppressive royal keepers. What’s more, Joe knows full well that Anya’s only pretending to be a commoner. Will these crazy kids ever come clean and make it work?
Who She Chooses: Monarchy.
Who She Loses: Joe Bradley.
Why She’s Wrong: If The Crown has taught us anything, it is that mid-20th-century royal families do not give two cents about the their younguns' personal happiness. Furthermore, this movie was secretly written by noted leftie Dalton Trumbo, feeding fuel to my fire that Roman Holiday shows us what not to do, instead of celebrating Anya's noble sacrifice. Resist the powers that be and hop on that motorbike with Gregory Peck!
Life Lesson: Hot dudes and freedom > Royal duty, especially when said duty is coded as the gong show that is the British royal family.
Roman Holiday, Paramount Pictures, 1953
Angela in Boomerang (1992)
Premise: The rare romcom centered on a man, this Eddie Murphy vehicle sees the comedian play suave businessman and rampant womanizer Marcus Graham. Marcus is used to calling the shots, until he dates Jacqueline (Robin Givens) and gets a taste of his own medicine. Will Marcus change his ways in time to start a genuine relationship with kind and artistic Angela (Halle Berry)?
Who She Chooses: Obviously Angela and Marcus end up together.
Who She Loses: Well, Angela misses out on forming a power-couple with Jacqueline.
Why She’s Wrong: Boomerang almost tells a satisfying “leopard changes his spots” story, but rushes through its third act and screws the pooch. Marcus ricochets between Jacqueline and Angela, cheats on everyone, and doesn't learn any lessons before sneaking into Angela’s workplace and begging her to get back with him.
As a sign that even the film’s writers couldn’t figure out why she’d agree, Angela says, “Give me one reason why I should take you back.” Marcus, like Boomerang’s viewers, is silent. This happens two minutes before they suddenly kiss and the movie ends. Um, what?
Life Lesson: To quote Oprah, “When people show you who they are, believe them.” That goes for you too, clearly conflicted Boomerang screenwriters!
Boomerang, Paramount Pictures, 1992
Sign up to our newsletter.
History’s most fascinating stories and darkest secrets, delivered to your inbox daily. Making distraction rewarding since 2017.
Lelaina Pierce in Reality Bites (1994)
Premise: Lelaina (Winona Ryder) is an aspiring filmmaker who must choose between capitalism and ~High Art~ in both her career and her romantic life. Will she go for Michael (Ben Stiller wearing a suit) and shill for a paycheck? Or will she follow her heart and hook up with Troy (Ethan Hawke with peak hair)?
Who She Chooses: Troy.
Who She Loses: Michael.
Why She’s Wrong: Troy uses the fact that he is Ethan Hawke in 1994 to convince Lelaina (and scores of women viewers) that a pretentious theory bro is better than a stable, considerate guy with a job. We’re meant to see Michael as a corporate sell-out, but dang, sue me for liking the dude who wants to help Lelaina make enough money to pay rent while also pursuing her aspirations to direct a documentary.
P.S.: Troy does what we'd now call "negging" by being mean to LeLaina when she wears a pretty white dress that looks like "a doily." Props to Michael who shows viewers the correct response by staring at her in awe and saying she looks beautiful.
Life Lesson: If Ethan Hawke wasn’t so good-looking, Troy would immediately read as the villain. Beware floppy hair!
Reality Bites, Universal Pictures, 1994
Kathleen Kelly (Meg Ryan) in You’ve Got Mail (1998)
Premise: After investing in a lifetime supply of emotional barriers, Kathleen (Meg Ryan) lets her guard down and begins a flirtatious AOL correspondence with a mystery man. But just when her personal life ramps up, her professional life tanks. Headed by smug businessman Joe Fox, a massive chain bookstore opens near Kathleen’s independent children’s book shop. The Barnes and Noble clone endangers her livelihood and confirms Manhattan’s soulless gentrification.
Who She Chooses: AOL Mystery Man Who Is Obviously Joe Fox.
Who She Loses: Frank Navasky (played by Greg Kinnear at his most charming).
Why She’s Wrong: I have never understood the fuss over this “love” story. The soundtrack is fine, I will grant you that, but what is romantic about capitalism crushing Meg Ryan's independent business? Man, there is a world of difference between Michael in Reality Bites and the monster that is Joe Fox in You’ve Got Mail.
Life Lesson: A movie for people who swoon as their loaded boyfriend burns their dreams to the ground and says, "It was just business, it wasn’t personal" (a real line from this movie's "romantic" climax!)
You
Erica Barry in Something’s Gotta Give (2003)
Premise: Erica Barry (a luminous Diane Keaton) is a successful playwright whose daughter brings home a much-older man named Harry (Jack Nicholson). When Harry, after a lifetime of womanizing and boozing it up, finally has a heart attack, he stays at Erica’s beach house to recover with the help of local Hot Doctor Julian Mercer (Keanu Reeves). After Erica’s daughter dumps Harry, he slowly learns to, gasp, consider dating a woman his own age. In the meantime, Harry faces stiff competition from Julian, who's into Erica as well. With her pick of the litter, Erica reconnects with her fun-loving, sensuous side.
Who She Chooses: Harry.
Who She Loses: Julian.
Why She’s Wrong: Keanu Reeves plays a beautiful doctor who just wants to take Diane Keaton on nice vacations and give her compliments. Exhibit A: Julian asks Erica out by writing his number on a prescription pad and implying a) that a date with Julian is what the doctor ordered and b) that his employment is gainful and based on both hospitality and intellect. He also specifies that dinner will be at seven, solidifying that Julian knows the correct time to pitch a date for a woman over 60. Jack Nicholson spends most of his time realizing that he is a Bad Man and sweating.
Life Lesson: When Keanu Reeves asks you on a date, say yes.
Something
Honorable Mentions:
Pretty In Pink (1986): Andie should have chosen her BFF Duckie instead of Blaine who is so spineless that he deserves to be named “Blaine.”
Friends (1994-2004): Rachel should have chosen sweet, dumb Joey instead of human trash-fire Ross.
Sex and the City (1998-2004): Carrie should have chosen independence/her friends instead of Mr. Big.
The Bachelorette (Season 15, 2018-2019): Hannah B. should have chosen Tyler C. or Pilot Pete instead of the philandering fivehead Jed Wyatt.
