Clockwise from bottom left: The West Wing (Screenshot: YouTube/Warner Bros. TV), House (Screenshot: YouTube/House, M.D.), Cheers (Screenshot: YouTube/Paramount+), The Nanny (Screenshot: YouTube/The Nanny)
With Will They/Won’t They, LaToya Ferguson digs into the classic and definitive uncertain relationships throughout the history of television and decides whether all of that waiting was even worth it.
What exactly is it about the will-they/won’t-they relationship that just hooks television audiences? Because while this particular trope can be comforting (the height of comfort television even), it can also be extremely frustrating(or “annoying,” to quote my own mother).
Drag out a will-they/won’t-they for either too long or highlight it too much and a show could be considered “ruined,” even when it finally puts the wanted pairing together. Even worse, a series could be unceremoniously canceled before it ever actually pulled the trigger and allowed the characters involved to reach a point of “they will.” However, end a will-they/won’t-they relationship too soon and the next question becomes “What’s next?” The classic worry here is that as soon as the central will-they/won’t-they couple is officially on solid, healthy ground—as soon as the unresolved sexual tension is completely resolved and no longer, well, tense—there goes the entertaining conflict. It’s “The Moonlighting Curse,” when certain series—that Cybill Shepherd and Bruce Willis show included—suffer after the official union. (Another irksome move is when series decide to add unnecessary conflict to their more stable pairings, holding onto the belief that there’s no drama or draw to a happy couple.)
The thing about the will-they/won’t-they relationship is, even if you’ve seen the type before—from the versions centered on unrequited pining to the enemies-to-lovers trope to workplace romances and so on—there’s always a reason why it’s such a go-to for the medium. So, there will definitely be a lot of overlap in the examples throughout this column. In fact, technically, Moonlighting itself falls under the umbrella of this debut piece’s jurisdiction. But I’ll be saving that one for later. Because the will-they/won’t-they relationship is an everlasting staple of television, and within this staple is a delightful number of subsets. Such as…
Who’s The Boss? (a.k.a. the employer-employee subset of will-they/won’t-they)
On television, a workplace romance tends to go one of two ways: Either two coworkers or partners of (relatively) equal standing get together or the employer and employee (or supervisor and supervisee) do the same. In the case of the latter, especially in sitcoms, there’s a bit of an idealized version of the power dynamic at play, usually with the “inferior” character ironically having the upper hand over the “superior.” (Though the optics of the two getting together can come into play as a roadblock of this particular type of will-they/won’t-they story.) In fact, there was a whole series titled after the question posed by this particular take on the will-they/won’t-they trope: Who’s The Boss?
Remington Steele (5 seasons, 1982-1987)
When it comes to the will-they/won’t-they relationship trope and the employer-employee subset of it, Remington Steele was truly a pioneer, especially for an hourlong series. It honed the type of witty banter audiences are now often accustomed to when it comes to this type of show. The question of who was really the boss loomed, as Laura Holt’s (Stephanie Zimbalist) plan to thrive as a private investigator via a fictitious male superior named “Remington Steele” paved the way for a mysterious con artist (Pierce Brosnan), whose own name was even a mystery to himself, to swoop in and assume the fake identity. As the two constantly fought for supremacy in their detective business, the sparks also began to fly.The give and take and the push andpull of this dynamic paved the way for the series’ success, to the point where even eventual cancellation didn’t stick. Now that’s a powerful will-they/won’t-they.
The fourth season of Remington Steele ended with Laura and Remington marrying, while the six-episode fifth season saw the pair faced with challenges to the very validity of that union. But even early on in the existence of the will-they/won’t-they trope, it was clear just how much the whims of a network could affect the conclusion to a story if things were drawn out too long.
Cheers (11 seasons, 1982-1993)
Remington Steele and Cheers essentially set the blueprint, not just for the employer-employee style of this kind of onscreen relationship but the will-they/won’t-they trope as a whole. Cheers’ legacy is interesting in that it did this particular version of this motif (also falling under the love-hate umbrella, which will be discussed in the future) twice, with Ted Danson’s Sam Malone on both sides of that dynamic.
For as funny as Cheers was, it managed to make its first go at the will-they/won’t-they relationship quite bittersweet. In the first five seasons, the dynamic was between Sam and Diane Chambers (Shelley Long), pitting his bawdy machismo against her delicate snobbery on a constant basis. As much as they claimed to be like oil and water, they were explosive when together—so much so that they would regularly break up. Sam and Diane dangled other partners in front of each other—including eventual spin-off character Frasier Crane (Kelsey Grammer)—both to prove that they had moved on and to make the other jealous.
Long’s last season sees Diane finally pester Sam enough to convince him to get married after a number of failed engagements. But when Diane gets an offer from a publisher that requires her to finish writing her novel, she promises she’ll only be gone from Boston for six months in a goodbye that Sam clearly knows is forever.
Long’s departure from the series ended one chapter but paved the way for a second. Kirstie Alley came to the series in the sixth season as Rebecca Howe, the manager (sent by new corporate overlords) of Cheers, eventually hiring back Sam, who had cashed out on the bar and bought a boat post-Diane’s departure. Much like Diane, Rebecca was buttoned up in comparison to Sam and the other Cheers stalwarts, but she came from the corporate world, not the academic one.
Despite flipping the familiar dynamic on its head, the Sam and Rebecca pairing was never portrayed as being as passionate as Sam and Diane. And even though the two did end up getting together, ultimately, Sam and Rebecca acknowledged they weren’t right for each other. (As this era of the series progressed, the employer-employee dynamic also shifted, with the two eventually becoming co-owners of the bar.) Cheers effectively had two series’ worth of will-they/won’t-they relationships with Sam Malone at the center, and it found a way to make them both distinctive.
Who’s The Boss? (8 seasons, 1984-1992)
And here is the titular example for this piece. So, was the boss Angela (Judith Light), theConnecticut advertising executive who’d figured out how to balance work and family as a divorced single mother making it in the 1980s? Or was it Tony (Tony Danza), the alpha male retired baseball player and widower that Angela reluctantly hired as her live-in housekeeper? (Spoiler alert: According to Community, the answer was, in fact, Angela.) Could they ever make it work, both professionally and romantically?
Though it’s one of the quintessential examples of this type of will-they/won’t-they relationship, Who’s The Boss? demonstrated the problems of waiting too long to answer things in the form of “they will.” Angela and Tony didn’t get together until the eighthand final season—and only did so to prevent the series from being canceled after its seventh round, though the move ultimately failed to boost ratings. The series concluded with a three-part episode (“Savor The Veal”) that saw Tony and Angela try and fail to make a long-distance relationship work, only for Angela to then try and fail to put Tony’s happiness and new dream job in Iowa first, then for Tony to give up said dream job and return to Connecticut to be with Angela, promising to look for other work in the area. The two got engaged in this final season, but apparently, the wedding never occurred as a promise originally made by the producers. And it’s not the last time long-term promises being kept (or broken) affected the outcome of a will-they/won’t-they.
In June 2022, the streaming service formerly known as Freevee (so, Prime Video) announced a Who’s The Boss? sequel series—as Melissa & Joey, perhaps, didn’t fully scratch that itch—with Danza and Alyssa Milano (as the potential “boss”) returning. However, in October 2024, Amazon officially killed that potential comeback. But the original Who’s The Boss?’s real legacy, outside of its former Nick At Nite and TV Land prominence, is as a template for the troubles of drawing out the will-they/won’t-they instead of striking while the iron is hot.
The Nanny (6 seasons, 1993-1999)
CBS’s The Nanny wasn’t just inspired by will-they/won’t-they series like Cheers and Who’s The Boss? It was part of an era of TV that could only exist right after those shows ended. The Nanny provided a ’90s edge that wasn’t happening in the warm ’80s world of Who’s The Boss? And while Cheers had barbs galore in the place where everybody knew your name, that was more a sign of how the show was ahead of its time than the norm—not to be mistaken with “NORM!”—of the era.
Fran Fine (Fran Drescher) often taught Mr. Sheffield (Charles Shaughnessy) a thing or three in between every nasally wisecrack. If you asked the question “who’s the boss?,” 10 out of 10 times, the answer would be Fran, and the series was never shy to let the audience know it. Nor was it sheepish about acknowledging Fran and Mr. Sheffield’s attraction and jealousy of each other’s relationships—or dangling the “they will” aspect in the audience’s face. Seventeen episodes into the first season, Fran, woozy post-surgery, freaks out Mr. Sheffield by telling him that she loves him. The next episode would feature their first kiss. By the middle of the second season, Fran and Mr. Sheffield had already smooched two or three times, often using the line “I could just kiss you!” literally in those moments. But the big scene was in the third-season finale, in which Mr. Sheffield told Fran he loved her during a spot of heavy airplane turbulence…only to take it back in the following season’s premiere.
While the audience obviously wanted Nanny Fine and Mr. Sheffield together, to do so for good would obviously mean abandoning the titular aspect of the series. But The Nanny did pull the trigger. By mid-fifth season, the two finally made it official, and their wedding hit in the season finale. The sixth and last season of the show depicted Fran reconciling with going from nanny to wife—as the “they will” of this series effectively changed its very premise—as well as having a baby. It provided a natural end for the series, right before things entered the television landscape of the 2000s, where sitcoms and will-they/won’t-they relationships would also shift further away from the “who’s the boss?”-style, power-dynamic-based premise.
The West Wing (7 seasons, 1999-2006)
The will-they/won’t-they doesn’t always have to come from a place of comedy or farce. In fact, a drama setting can derive even more tension from these types of relationships. So, while the trope was spawned more from the dramedy and comedy sector, it has managed to thrive on the purely dramatic front as well. In the case of Aaron Sorkin’s The West Wing, that will/they-won’t-they relationship was between Deputy Chief Of Staff Josh Lyman (Bradley Whitford) and his senior assistant Donna Moss (Janel Moloney), which wasn’t even originally supposed to be the case. Here, the series pivoted from its initial attempt to have a will-they/won’t-they with Josh and his ex-girlfriend Mandy (Moira Kelly)—a character that ended up only lasting on the show for a season—to the relationship that it would be remembered for.
The show slow-playedthis pairing, with the two not even getting together until the final season. (Executive producers Aaron Sorkin and Thomas Schlamme were very into the sexual tension of the relationship, which the series did maintain even after they left after the fourth season.) To close out The West Wing, Josh and Donna ended up on equal professional footing—unlike in the aforementioned comedies, this dynamic was treated as more of an obstacle—as he became the White House Chief Of Staff and she the First Lady’s Chief Of Staff.
House (8 seasons, 2004-2012)
In true The Nanny fashion and in keeping with asking who really is the boss, drug addict and medical genius Dr. Gregory House (Hugh Laurie) would seemingly always—especially in a professional context—come out on top against his put-upon supervisor, hospital administrator Dr. Lisa Cuddy (Lisa Edelstein). But things became very muddled as House went on, and with that messiness came the disappointment of the House/Cuddy will-they/won’t-they.
When House and Cuddy finally “got together” in the fifth-season finale, “Both Sides Now,” it all ended up being detox-induced hallucination—a moment often considered to be when the series jumped the shark. The following season would begin with House in a mental health facility, detoxing with Lin-Manuel Miranda’s Alvie, and it would continue with him attempting to pursue an actual relationship with Cuddy—only to realize it was too late. While the sixth season ended with House and Cuddy finally actually in a relationship, by the following run of episodes, they were broken up, with House literally crashing into her pad. That ended up also being Edelstein’s final episode as a series regular. And honestly, who could blame her?
30 Rock (7 seasons, 2006-2013)
Not every will-they/won’t-they relationship has to end with the answer “they will.” Nor does it have to “actually” be a will-they/won’t-they. Just take a look at Liz and Jack on 30 Rock.
To talk about Liz Lemon (Tina Fey) and Jack Donaghy (Alec Baldwin) in this particular context is to also acknowledge them as a successful subversion of the trope. In a sense, the Liz/Jack relationship did have something of a My Fair Lady tinge to it at times, one that suggested the two characters would find their way to each other when all was said and done. While 30 Rock certainly poked fun at the very idea of Liz and Jack as a romantic pairing, it never actually pulled the trigger on such a decision. (Those who considered Peggy and Don from Mad Men a potential will-they/won’t-they relationship could also see them as a dramatic—as funny as that show could be—version of this. Those who don’t consider that at all can also continue to not do that, same as with Liz and Jack.) Plus, the ultimate Liz/Jack ’shipper (and will-they/won’t-they aficionado) within the universe of the show was Kim Jong-Il (Margaret Cho), who moaned: “All I want is Jack and Liz get together. On Friends, it was so satisfying. They do on Cheers, they do on Moonlighting. Everybody do it! Don’t overthink it, writers. Whoever you are.” And this just about gave us all we needed to know about Tina Fey and Robert Carlock’s thoughts on this particular matter. Plus, in Tina Fey’s own words: “Liz and Jack will never be together. Not even if we go fifteen seasons. Okay, if we get to season fifteen, they’ll do it.” It’s pretty much the definitive “they won’t,” which, as we’ll see throughout this series, is actually quite hard to come by.
Next time: unrequited pining (a.k.a. the “after all these years” scenario)
