Television’s All-Time Greatest Will They, Won’t Theys

One of television’s most widespread, and most welcome, recent trends is the rise of the genuine romantic comedy — a show that doesn’t simply build up to two characters’ relationship, but follows it as it deepens and develops. Still, television has excelled at long-running romantic plot lines for years, just in a slightly different incarnation: the Will They, Won’t They, in which a love connection develops (or doesn’t) over a period of years, with lots of tension and mishaps in between. In honor of Valentine’s Day, here are ten of the trope’s most iconic examples, from the ’80s sitcom to the modern antihero drama.

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Sam and Diane, Cheers

The OG Will They, Won’t They, even though they eventually didn’t — in fact, Shelley Long wasn’t a series regular for more than half of Cheers’ eleven seasons. Still, the opposites-attract dynamic between Ted Danson’s womanizing baseball player turned bartender and Long’s pretentious cocktail waitress practically defines the tension and conflict that make so many Will They, Won’t Theys, including theirs, last for years rather than mere weeks. 

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Niles and Daphne, Frasier

It’s only fitting, then, that another Will They, Won’t They for the ages is a direct spinoff of Sam and Diane, both because Frasier itself is a spinoff of Cheers and because Frasier the character was initially one of Diane’s non-Sam love interests. On his own show, Frasier’s brother gradually begins a relationship with his father’s British live-in housekeeper — though only after a years-long, unrequited crush and lots of drama about class differences. It ends, unlike Sam and Diane, with marriage.

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Mulder and Scully, The X-Files

Patient Zero of a longstanding, absurdly prolific subgenre of the Will They, Won’t They: the law-enforcement-turned-potential-life-partners, often comprised of a male eccentric and a female skeptic. The list goes on and on — Castle and Kate (Castle), Peter and Olivia (Fringe), Stabler and Benson (Law & Order: SVU) — but no one will ever do it better than Fox Mulder and Dana Scully, which is why none of those other shows have a limited reunion currently averaging more than ten million viewers an episode. 

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Ross and Rachel, Friends

Perhaps the most committed entry on this list to keeping “Will they or won’t they?” a genuine and open question. Just look at this insane ten-season timeline of make-ups and break-ups and marriages and divorces and getting off of planes! After every member of the friend group had run through every possible romantic pairing with both each other and outsiders, they obviously ended up together, but kudos to Friends for keeping up the angst for a full decade.

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Fry and Leela, Futurama

Animated characters (and one-eyed aliens, and time-traveling pizza delivery boys) have feelings too, so Matt Groening’s less-well-regarded-but-still-pretty-great creation earns a spot for its central not-quite-pairing. It’s a classic case of an underachiever guy being wowed by and gradually winning over a hyper-competent woman, but considerably funnier, and a rare example of the woman’s feelings seeming earned rather than handed over. Capped off by a genuinely sweet ending involving yet more time travel and we have an underrated classic.

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Josh and Donna, The West Wing

In retrospect, the drawn-out process of a solid work marriage becoming a potential actual marriage has more to do with Aaron Sorkin’s relative disinterest in romance relative to The West Wing‘s other themes. But on the screen, the chief of staff and his assistant got seven full seasons to oh-so-slowly recognize their feelings for each other, complete with a payoff that’s one of the major reasons why season seven managed to buck the show’s post-Sorkin creative slump.

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Lorelai and Luke, Gilmore Girls

And while we’re on the subject of “relationships built on a solid foundation of fast and ridiculously dense banter,” let’s get to the resident diner owner and caffeine consumer extraordinaire of one Stars Hollow, Connecticut. While Rory’s major love interests are legion, Gilmore Girls’ six seasons were a slow and steady progress from flirtation to full-blown marriage for these two (who Lauren Graham thinks remain hitched to this very day, though we’ll find out for sure in the upcoming Netflix revival).

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Jim and Pam, The Office

Remember when the entire country was so psyched that this Will They, Won’t They finally did that their completely fictional wedding made the cover of a national magazine? Such is the power of nearly five seasons of absurdly cute build-up. But even though the later seasons of The Office are rightfully considered the show’s weakest, the decision to seriously explore Jim’s dissatisfaction and the ensuing strain on Jim and Pam’s relationship arguably elevates the couple to one of TV’s all-time greats.

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Starbuck and Apollo, Battlestar Galactica

Lee and Kara are the exception that proves the rule: the Will They, Won’t They that genuinely didn’t. (Like, really didn’t. Starbuck-married-someone-else-and-stayed-that-way didn’t.) But the chemistry and camaraderie between the friends, almost-in-laws, and military comrades is undeniable; Starbuck even committed the PG-13 version of Ross Geller’s most infamous faux-pas by calling Gaius someone else’s name during sex. That’s real, albeit repressed, love right there.

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Stan and Peggy, Mad Men

Sometimes Will They, Won’t Theys are all the more satisfying for their subtlety. Peggy and Stan’s relationship was hinted at just enough to feel right, but kept low-key to the point where their mutual confession of love — and intra-office phone call turned embrace straight out of a Nora Ephron movie — felt like a triumphant surprise. Because, Sinatra dances aside, Peggy and Don was never going to happen, and this particular couple is way healthier for all parties involved.