1. Carrie Bradshaw and Aiden Shaw, Sex And The City
While it was apparently always in the cards for Carrie Bradshaw to get together with Mr. Big, that doesn’t mean it wasn’t heartbreaking to see the relationship columnist absolutely tank her relationship with Aiden Shaw, the big, perfect furniture designer with a heart of gold. Bradshaw’s struggles with commitment (and cheating) ultimately led to the long-term relationship’s demise, but fans have long argued that Aiden would have been a better choice than Big, whose real name is John James Preston. Whereas Big is over the top and experienced, Aiden is stable and head-over-heels in love with Carrie. And while Aiden eventually settled down, got married, and had three sons—Homer, Wyatt, and Tate—with someone else, when the two ex-lovers run into each other in the second movie and on the show, it still always seems a little wistful, like they both just glimpsed the one that got away.
2-3. Dan Humphrey and Olivia Burke/Serena Van Der Woodsen and Nate Archibald, Gossip Girl
Being a teen soap on The CW, Gossip Girl churned through romantic pairings with the ferociousness the network’s current offerings apply to plot points. But only one of the show’s love connections was so strong, its participants even overcame the fact that they were legally brother and sister for a spell: Dan “Lonely Boy” Humphrey and the tabloid-fodder love of his life, Serena Van Der Woodsen. Though their initial courtship fueled the never-bettered tawdriness of the show’s first season, the Dan-Serena coupling ultimately proved to be the most boring aspect of Gossip Girl—with the exception of Serena’s occasional bedfellow, Nate Archibald. The greatest service Chace Crawford ever afforded to the show was keeping Dan and Serena apart in season three, the realization of a lifelong crush that could’ve kept both parties from ever again playing wet blanket to the meddling of their castmates. While his beloved “S” was otherwise occupied, Dan shacked up with Manhattan interloper Olivia Burke, a movie star seeking the “real life” experiences afforded by a semester at NYU. Hillary Duff’s six-episode stint wasn’t long enough to make any real dent in Dan and Serena’s destiny—but six episodes free of a sulky Penn Badgley is reason enough to wish she’d stuck around longer.
4. Rory Gilmore and Jess Mariano, Gilmore Girls
As played by Milo Ventimiglia, Jess Mariano is a leather-jacketed bad boy as only Gilmore Girls creator Amy Sherman-Palladino could envision him: Brooding and alienated, certainly—though those characteristics could very well be the affectations of a teenager obsessed with the Beats. Jess roars into the idyllic Connecticut hamlet of Stars Hollow looking like an everyday ne’er do well, but town golden child Rory Gilmore eventually sees through that prickly exterior. Rory’s kindness is of tremendous benefit to Jess’ standing within the community—the romantic relationship that follows is of similar benefit to the show as a whole. The love triangle between Jess, Rory, and Rory’s guy-next-door boyfriend Dean Forester is Gilmore Girls at its absolute soapiest, but the tension drives some of the series’ best episodes, like the dance marathon-centric “They Shoot Gilmores, Don’t They?” Rory and Jess make for a fitting intellectual match, and they challenge one another in ways the hometown-sweetheart dynamic between Rory and Dean doesn’t. In the end, however, they’d encounter their own insurmountable obstacle: Windward Circle, in which Jess’ Jack Kerouac routine clashes with a California setting this time.
5. Jo March and Theodore “Laurie” Laurence, Little Women
Perhaps realistic, but nonetheless depressing, Laurie’s marriage to Amy in Little Women is one of the worst mistakes in literature. The idea of two people giving up on their aspirations to settle for each other seems like a direct path to partner loathing, and although Amy and Laurie eventually adapt to each other, as artless fogies with little in common other than their children, one can’t help but wonder how both Jo March and Laurie would have flourished had they married. With a meeting of the minds that strong, they could have had the family and the futures each had dreamed about instead of settling for individual couplings that leave a lot to be desired.
6. Andie Walsh and Phil “Duckie” Dale, Pretty In Pink
John Hughes is held in high regards for his ideal portrayals of high school cued to all the right music. That doesn’t mean he always got the plot right, though, something that’s most apparent in his 1986 film Pretty In Pink. From the beginning, Duckie is the obvious match for Andie. His unwavering respect for her is clear right up to the end of the movie when, despite how enamored he is, he selflessly encourages a relationship with the bland Blane McDonnagh. Test audiences are to blame for this horrible ending, as the original paired Andie and Duckie together to poor reception. Never mind that Blane was too embarrassed to take Andie to the prom, because now OMD’s “If You Leave” is playing and the two are making out in a misty parking lot. More importantly, one of them is rich and in the ’80s that mattered most. A year later, Hughes reversed this mistake—presumably shunning any test audience’s thoughts—with Some Kind Of Wonderful, which grants two, meant-to-be misfits—Keith and Watts—a happing ending.
7. Jim Halpert and Karen Filippelli, The Office
Jim and Pam were fated to get together from the first frame of The Office, if only because that’s how it went in the U.K. original. But the show was able to make the will-they/won’t-they drama stretch out over a few years, first by pairing Pam with lunkheaded fiancé Roy, and then by moving Jim to Stamford and getting him together with Karen. Karen could have very easily been a villain role—someone like Roy, who’s simply a bad match for our hero that the audience can root against. But as Rashida Jones plays her, Karen is likable, smart, and a good match for Jim. She’s also everything Pam isn’t—confident, ambitious, and willing to call Jim on his shit. As the show played with the idea of Jim stepping up and taking responsibility throughout its run, it’s not hard to imagine an alternate story where Jim moves to New York with Karen and pursues a new life instead of staying in the comfortable rut of the show’s later seasons.
8. Donna Pinciotti and Steven Hyde, That ’70s Show
Many sitcoms are built around a will-they/won’t-they romance, but That ’70s Show was built around a yes-they-will-and-pretty-soon-at-that between Donna (Laura Prepon) and Eric (Topher Grace). Early on they toyed at a love triangle between the two and Eric’s best friend Hyde (Danny Masterson), but soon dropped the idea and stuck with the central romance long after it was clear the characters were a terrible match. In the later seasons, Donna became an adventurous and aspiring rock journalist, eager to leave their small town behind, while Eric remained a whiny perpetual child. Cynical, worldly Hyde seemed like a better match for Donna with each passing season, but the show never followed up on the idea, even after Grace left the series to pursue his movie career.
9. Nick Miller and Julia Cleary, New Girl
Part of New Girl’s ongoing success is due to the show recognizing the flaws in its characters and adjusting accordingly (apart from Winston, who just doesn’t get any storylines). Max Greenfield’s Schmidt was the obvious success story, becoming the show’s breakout character after a rough start. But the flaws in the lead character, Jess, were laid bare in Lizzy Caplan’s first-season arc as Julia, the boozy, troublemaking lawyer girlfriend of Jess’ eventual beau, Nick. With Zooey Deschanel still playing Jess in full-on “adorkable” mode, Julia was a refreshing splash of cold water on the series, as a female character with a career, strong opinions, and bigger things going on in her life than cupcakes and bangs. Things came to a head between the two women in Caplan’s second episode, “Jess & Julia,” where Julia levels every criticism much of the audience had towards Jess at that point—for example, that she was an often irritating flake who can’t navigate the adult world. Jess makes a big speech about how all her cutesiness “doesn’t mean I’m not smart and tough and strong.” The show treats that as a rousing affirmation for Jess, but in truth, she was none of those things at the time. Over the next season or so, Jess became less cloying, and the show improved in nearly every area. But at that moment in season one? Not only did Julia make a better match for Nick, it was hard not to want to see Deschanel banished to some forgotten corner of Etsy so the show could be turned over to Caplan. Newer Girl? It could’ve worked.
10. John “Scottie” Ferguson and Midge Wood, Vertigo
Scottie (James Stewart), the detective hero of Alfred Hitchcock’s romantic nightmare movie Vertigo, is hired to tail the beautiful, remote, death-obsessed Madeleine (Kim Novak), who seems to have stepped off the cover of a Gothic romance novel. (She’s borrowed her look from a portrait of a dead woman named Carlotta, with whom she is unhealthily obsessed.) Scottie falls in love with her, despite all the signs that something is not right, in spite of the sound counsel he gets from his best friend and soft place to fall, Midge (Barbara Bel Geddes). The adorable Midge, a talented artist who works in commercial illustration, sketching brassiere ads because a girl’s got to eat, is everything that the high-strung, easily duped Scottie could use more of in his life: She’s nurturing, emotionally open, practical-minded, and clear-sighted. And clearly her tolerance for his moony side speaks to the depth of her feelings for him. But when she tries to simultaneously declare her love and puncture the bubble he’s living in by painting a portrait of herself in the style of the portrait of Carlotta, Scottie can only mumble that it’s “not funny” and turn away, appalled. It’s his loss. The film ends on a tragic note, but for Scottie, the real tragedy comes around the midway point, when Midge simply disappears from the movie, signaling that he has become so lost in his fantasy of a chastely unattainable “perfect” love with a woman who doesn’t really exist that he can no longer even be on friendly terms with the woman who offers him the promise of the real thing.
11. Scott Pilgrim and Knives Chau, Scott Pilgrim Vs. The World
Though Edgar Wright’s kinetic adaptation of Bryan Lee O’Malley’s Scott Pilgrim graphic novels is ostensibly about a slacker’s quest to defeat his new girlfriend’s seven evil exes, it doubles as a study of a couple that’s probably too emotionally immature to be in a relationship in the first place. Michael Cera’s aloof Pilgrim and Mary Elizabeth Winstead’s distant Ramona Flowers have such little spark that even after seven epic battles their happy ending together rings hollow. Chemistry wasn’t an issue, though, for the title character and Ellen Wong’s Knives Chau, the plucky high school student whose history with Scott further complicates his relationship with Ramona. In the end it was Scott’s combat rapport with Knives, not Ramona, that enabled him to take down Jason Schwartzman’s final boss, leaving viewers to wonder if it shouldn’t be those two paired together in the final frame. Turns out the filmmakers entertained the same thought: In the movie’s far sweeter original ending, filmed before O’Malley had finished his comics, Scott and Knives head off into the sunset en route to a date at the arcade.
12. Diane Chambers and Frasier Crane, Cheers
It speaks to Kelsey Grammer’s comedic charisma and the adaptability of the Cheers writing staff that Grammer’s Frasier Crane, originally introduced as yet another hurdle in Sam and Diane’s on-again, off-again relationship, became one of the show’s most consistent scene stealers and one of the bar’s most well-rounded regulars. Frasier, of course, went on to outlast Diane at Cheers before anchoring his own long-running spinoff, making him the most successful late-addition romantic foil in sitcom history. Had Diane never left him at the altar, though, she would have found everything she never could in Sam; a sensitive man who shared and respected her interests, Frasier would have provided her the means and encouragement to pursue her literary passions. Cheers was ultimately a show deeply distrustful of people moonlighting outside of their class, so Sam and Diane’s relationship was always damned by social constructs. Diane and Frasier, though, could have worked.
13. Josh Lyman and Amy Gardner, The West Wing
In The West Wing’s third season, Bradley Whitford’s romantically clueless Josh Lyman and Janel Moloney’s politically clueless Donnatella Moss were an inconveniently dynamic pair onscreen. Josh and Donna weren’t written to be eventual love interests, but Lyman’s constant patter with his assistant became some of the most memorably human of the show—a chemistry that arose naturally between two characters who didn’t have anyone else they felt close to. To throw a wrench in the works, the show threw Mary-Louise Parker’s Amy Gardner at Josh. Amy was a fast-talking, modern feminist with an axe to grind and no fear whatsoever about getting involved with Josh. Josh and Donna do finally end up together at the end of the show’s seventh season, but it always was a shame about Amy. The show never knew what to do with her, which meant that her relationship with Josh was awkward and inconsistent. Because Josh’s chemistry was diverted elsewhere, there didn’t seem to be a lot left over for Amy, and even the writers weren’t that excited about her. She was demonized for her political maneuvering and her blunt attitude, especially in comparison to Donna’s mild, deer-in-headlights appeal, but that type of Washington wonk makes a lot more sense with the politically obsessed stats junkie who became the White House deputy chief of staff. Amy Gardner was beautiful, intelligent, and confident, and Josh was crazy about her in some respects. But she was never going to be taken seriously as a love interest while Donna was still in the picture, and her character development suffered for it.
14. Rick Blaine and Ilsa Lund, Casablanca
In 1942, no one who came between a married couple was going to be with the partner they loved by the end of the film—decency laws and public outcry were real threats. So there was never much of a chance for Casablanca’s Rick and Ilsa, who fall in love with each other in the middle of war-ravaged Paris, just weeks before the Nazi occupation. The two are surrounded by despair, isolated in their shared expatriate state, and unmoored from their roots. There wasn’t a lot going for them except, as Harry points out in When Harry Met Sally, the best sex of their lives. When Ilsa’s husband Victor Laszlo turns up alive and well, the plot gently ushers Ilsa back into the arms of her betrothed. Paul Henreid, who plays Laszlo, is tall and blond and humanitarian, sure: But Humphrey Bogart is Humphrey Bogart. Rick is a wreck of a man, constructed purely of avarice and a broken heart; the rest is cigar smoke and whiskey. But the tragedy of the movie in many ways is that Rick is just a speed bump in Ilsa’s life, a sideshow on the way to (and from) the main event. But she really did love him, given all that. Ilsa’s passion for him is eternal, even if she knows better. And after that heartbreaking final scene on the tarmac—one of the most iconic in film history—it’s hard to imagine that she doesn’t spend that flight, that night, and maybe the rest of her life thinking about the life she would have had in Casablanca.
15. Sydney Bristow and Will Tippin, Alias
Poor Will Tippin. Right from the pilot of Alias, Will is Sydney’s other love interest, the friend that gets upset about her engagement to Danny Hecht and tries to investigate SD-6 to help her out. Will is played by Bradley Cooper in one of his earliest roles—a scruffy reporter who’s digging out the truth about a weird criminal organization. But he’s never positioned as a legitimate love interest, despite the chemistry he has with Jennifer Garner’s Sydney and the naturalism he brings to the show. Instead Sydney is shunted into a relationship with her CIA handler, and Will is relegated to the role of awkward friend, romantically interested, frequently jealous, but never a heavyweight. But Sydney’s relationship with Vaughn gets increasingly weird, despite Michael Vartan’s pretty face, as the relationship begins to mirror the real-life relationship and then breakup of Jennifer Garner and Michael Vartan. Will’s life ends up destroyed by his affection for Sydney, mostly because there’s no legitimate reason for him to be on the show anymore, so the writers kept making increasingly awful stuff happen to him. A real relationship—or at least a more serious consideration of it—between Sydney and Will could have been lovely.
16. Bridget Jones and Daniel Cleaver, Bridget Jones’s Diary
Bridget Jones, Helen Fielding’s character and erstwhile icon of flummoxed women everywhere, probably ended up with the right guy in Mark Darcy, yet there’s a bit of an argument to be made that she should have landed in bed permanently with the super suave Daniel Cleaver. Maybe not in the first two Bridget Jones books, but in the third, Bridget Jones: Mad About The Boy, Jones is newly widowed and struggling to find love. While Cleaver does have (incredibly inconsequential spoiler alert!) a slight emotional breakdown in the book, Jones is all torn up over the guy she’s actually dating, Roxter, some 30-year-old who ultimately dumps her because she’s too old. The self-conscious heroine does ultimately end up with someone closer to her own age, but is Cleaver really all that bad? He’s clearly still in some sort of love with Jones, and he’s her children’s godfather. Plus, in the second iteration of the original Independent column, Jones had a child and moved in with Cleaver, even though Darcy wasn’t entirely out of the picture.
17. Melanie Smooter and Andrew Hennings, Sweet Home Alabama
While the entire plot of Sweet Home Alabama hinges on Reese Witherspoon’s Melanie Smooter realizing that, hey, maybe the South isn’t so bad after all, there’s also not that much wrong with the north, especially when it’s personified by Patrick Dempsey. Dempsey’s Andrew Hennings might know Melanie Smooter as Melanie Carmichael, and their relationship might not be as fiery as the one she has with her (long estranged) husband, Jake Perry, but he’s a nice guy, and, as the mayor’s son, one that clearly has a lot of stuff going for him. Melanie and Andrew even make it through the revelation of her fake identity. It’s all for naught, though, as Andrew ends up jilted at the altar after Melanie tells him she’s still in love with Jake. Andrew says he understands, but please; that’s humiliating. While Josh Lucas is charming as Perry, it’s hard to believe that Smooter would have just upended her life and career in New York because her old husband makes fancy glass art.
18. Erica Barry and Julian Mercer, Something’s Gotta Give
The entire point of Nancy Meyers’ Something’s Gotta Give is that old people should end up together, no matter if younger, better matches are available. At odds when they meet, Jack Nicholson’s Harry, an elderly cad, and Diane Keaton’s Erica, a feminist playwright, dance around their mutual attraction before finally getting together in the end. But Erica is also wooed by Julian, an attractive doctor (Keanu Reeves) who respects her intelligence and creativity. While it’s great to see Nicholson end up with a woman his own age on the silver screen, it’s obvious that Reeves’ hunky MD is a much better fit for Keaton. Even the film seems to tacitly understand that, having Julian get out of the picture by simply giving up, telling Erica he senses she still loves Harry. If only he was a bit more selfish, Erica would have gotten a better deal in the long run.