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. This month, she looks at Love-Hate (a.k.a. the Enemies-To-Sweethearts subset of will-they/won’t-they).
Now here’s where things really get tricky. For the most part, employer-employee (or supervisor-supervisee) is pretty cut and dried when classifying a specific type of the will-they/won’t-they relationship trope. But as noted since the first entry in this column, when it comes to the rest, there is a lot of overlap.
Moonlighting (the series that is arguably the reason for this entire column’s existence), naturally, belongs in the love-hate category. But doesn’t it also kind of belong in the partners category? (The answer is, “Yes, it does,” for those waiting for that entry.) And while Remington Steele ended up under the employer-employee designation, one could also argue that it belongs in (the future category of) partners…or also love-hate. Despite the “hate” part dissipating as soon as “love” came into the picture, do Dawson’s Creek’s Joey Potter and Pacey Witter count here or is that still more coming-of-age or after-all-these-years situation (not to even bring up the Dawson Leery of it all)? And what about Cheers, a show that was covered in the employer-employee piece despite defining the love-hate relationship in sitcoms through two central relationships?
The answer is, like most of these couples, complicated.
To this day, the love-hate will-they/won’t-they relationship of private investigators Maddie Hayes (Cybill Shepherd) and David Addison (Bruce Willis) is still considered the measuring stick for how to properly present this dynamic on television. At the same time, people talk about this show with the hope that others won’t fall victim to “the Moonlighting curse.” The curse, of course, is that officially putting the will-they/won’t-they relationship together—thus eliminating all of that previous sexual tension and the metaphorical juice of the whole situation—will lead to both the series and its main pair’s demise. After all, a happy couple is a boring couple.
Much like the discourse surrounding Keri Russell’s haircut in the second season of Felicity, “the Moonlighting curse” was initially one that boiled things down to a specific cause for lower ratings and series “failure.” (Felicity did not die after the second season and instead was granted two more, making the college-set series last the length of a stay on campus. Meanwhile, Moonlighting got Maddie/David together in the third season, the peak of its ratings, and the series ended in its fifth.) The penultimate episode of the third season, “I Am Curious, Maddie,” saw the consummation of the Maddie/David relationship, with the two characters finally acting on their clear sexual tension.
But like a future series that owed a lot to Moonlighting in its DNA, Castle, by the fourth season, Willis and Shepherd barely had any screen time together. The series’ issues had also mounted due to a combination of factors ranging from a pregnant Shepherd and Willis filming Die Hard (and his burgeoning film career after that) to the pair’s personal friction and a lot of production woes. (The latter caused reruns to air in place of incomplete new episodes, and series showrunner Glenn Gordon Caron was let go at the end of the third season due to problems with Shepherd.) What’s more, there were scheduling conflicts (like the 1987 World Series and the 1987-1988 WGA Strike that cut production on the season finale short). The fourth season finds Maddie and David rarely in the same scene—or even state—and instead fills the airtime with fantasy sequences (including one in which Maddie and David are in claymation), near misses between the two, third-party characters communicating with Maddie and David to relay messages, an episode where neither Shepherd nor Willis appear at all, and a season finale that ends with a musical number (that even mentions the ratings failure of the aforementioned Shepherd/Willis-less installment).
While the fifth and final season brings Shepherd and Willis (and Maddie and David) back together and works to rekindle that love-hate tension that drew audiences to the series in the first place, the damage had already been done. Essentially, the show did answer the will-they/won’t-they question with regards to them finally hooking up. But it never followed up on actually having them be a couple.
A Different World (six seasons, 1987-1993)
The bougie Southern belle and the hopelessly out-of-his-league nerd that just wants her to give him the time of day? On the surface, the bond between A Different World’s Whitley Gilbert (Jasmine Guy) and Dwayne Wayne (Kadeem Hardison) had all the makings of an unrequited will-they/won’t-they, with the just-wear-her-down dynamic coming into play as it has with so many other television relationships. In fact, had Lisa Bonet remained the lead of A Different World (the show was a college-focused spin-off vehicle for her Cosby Show character, Denise Huxtable), her coed might have had a similar energy with Dwayne.
Instead, A Different World took Whitley and Dwayne’s antagonist dynamic (and supporting-character roles) from the first season and turned it into series lead romantic fodder, beginning early in the rebooted second batch of episodes. The fourth installment of the season, “Dream Lover,” introduces the two characters refusing to accept the truth, as Dwayne starts to realize how attractive Whitley is (despite her personality) and Whitley has romantic dreams about Dwayne (despite his personality). Immediately, the live studio audience is falling all over themselves, literally screaming once the two characters finally kiss—in a dream sequence, of course…and then accidentally for real just moments later. Eventually, both characters back off on the possibility that they like each other—without even talking about what’s happening—but in terms of the show dipping its toes into the romantic waters of Whitley/Dwayne, the audience (both live and viewing) had already invested in them.
From there on, the denial continued, but the sentiments remained. The top of the fourth season saw Whitley finally ready to admit her feelings for Dwayne—after a summer of receiving romantic letters from him—only to discover that he returned from summer break with a new girlfriend. But Whitley and Dwayne finally got their act together in the eighth episode of the season, confessing their love for each other and officially beginning a romantic relationship. This led to all the other obstacles that the pair would face for the rest of the series, including the season-five moment when Dwayne crashed Whitley’s wedding to another man and proclaimed his love for her (and desire to marry her—for the second time during the series).
The sixth and final season sees Whitley and Dwayne as newlyweds, navigating that new terrain but finally on solid relationship ground—with Whitley learning in the series finale, as she and Dwayne are set to move to Tokyo for his new job, that she is pregnant.
For a generation of Black fans, Whitley and Dwayne were television “couple goals.” But like with plenty of other iconic will-they/won’t-they pairings—à la Friends’ Ross/Rachel or Gossip Girl’s Chuck/Blair—there has also been a lot of relitigation of the couple in recent years, naturally focused on the hate (particular from Dwayne’s end) part of the love-hate situation and whether or not Dwayne was another “nice guy” trying to dim Whitley’s shine once they finally got together.
Living Single (five seasons, 1993-1998)
Imagine that The Muppet Show’s Statler and Waldorf were two twentysomething Black professionals living in Brooklyn in the ’90s. Then imagine them channeling all their snarky energy at each other instead of The Muppet Show itself. Pretty sexy, right?
At least, that’s what Living Single realized in the case of Maxine Shaw, attorney at law (Erika Alexander), and stockbroker Kyle Barker (T.C. Carson). Both Alexander and Carson brought their own style to their respective characters’ barbs and asides, but the electricity came from Max and Kyle as sparring partners themselves. And it wasn’t a dynamic the series ended up discovering but instead one baked into its DNA, as the fourth episode has Max roping a reluctant Kyle into pretending to be her boyfriend (another tried-and-true romantic trope) to make an ex jealous. This is a task that Kyle, as Max’s “ebony prince,” gleefully turns into a game of overly romantic chicken with Max. The end of the season sees Max and Kyle waking up in bed together after a tequila-soaked night. No muss, no fuss: The will-they/won’t-they question is answered then and there.
Maxine and Kyle would continue to verbally joust throughout the series—whether they were still hooking up, actually in a relationship with each other, or just back to being romantically unattached. The couple would give it a go in the third season, until Kyle dumped Max for their relationship being what it always had been: heavy on the hate, light on the love. But by the fourth season, they were back together and dating in secret. The fifth and final season would see Kyle written off the series as a regular (which T.C. Carson has claimed was retaliation from Warner Bros. for speaking up on behalf of the cast), but even that couldn’t stop the animal attraction that was Maxine/Kyle. In the last episodes of the show, Max decides to have a child via sperm donor…only to discover in the finale that the anonymous donor whose profile she was drawn to was, in fact, Kyle.
For fans of both the Maxine/Kyle pairing and closure, the UPN series Half & Half (for which Living Single creator Yvette Lee Bowser served as showrunner) ended up providing a true conclusion to their story in its third season. Both Alexander and Carson reprised their LS roles in that season’s fourteenth episode, confirming they ended up together, were raising their now-seven-year-old daughter, and were still going off on each other every chance they got.
The Nanny (six seasons, 1993-1999)
Obviously, the most apparent will-they/won’t-they relationship on The Nanny was between Fran Fine and her employer, Maxwell Sheffield. But while the showeventually reached a natural conclusion once “Nanny Fine” and “Mr. Sheffield” were finally a couple and she was no longer his employee, it still had a will-they/won’t-they relationship. In fact, it had one with a far less obvious “they will” attached to it with the love-hate (well, hate-hate) pairing of the series: Niles (Daniel Davis), the deadpan Sheffield family butler and chauffeur, and C.C. Babcock (Lauren Lane), Maxwell’s snob of a business partner. Throughout the show’s run, C.C. has an unrequited crush on an oblivious Maxwell, which is even more threatened by the presence of Fran in the Sheffield household. In theory, this would’ve led to a love triangle of sorts between C.C., Maxwell, and Fran, with C.C. as the Baroness Schraeder to Maxwell’s Captain von Trapp and Fran’s Maria. Instead, C.C. remained on the outside looking in for most of the series, with Niles always waiting in the wings to verbally eviscerate her in the process.
While Niles and C.C. had all of the ingredients of a proper love-hate relationship, the pairing was basically the antithesis of what the will-they/won’t-they trope has become known for: long and drawn out, with contrived obstacles preventing them from getting together. Throughout the series, there were little moments—such as accidental kisses—that comedically presented the idea of the two fan favorites as anything other than enemies. However, it wasn’t until the sixth and final season that the two characters’ hate transformed into something akin to love, as yet another one of their barb sessions suddenly became a make-out one. After that, their relationship as a romantic pairing went through a speed run to the point of C.C. and Niles marrying each other (after multiple proposal rejections on C.C.’s end) in the series finale and learning that C.C. is carrying Niles’ baby. Rushed and fan-servicey, perhaps, but considering the struggles and fates of plenty of other will-they/won’t-they couples, things could have been much worse.
Buffy The Vampire Slayer (seven seasons, 1997-2003)
In terms of will-they/won’t-they relationships, Buffy The Vampire Slayer had quite a number to choose from—both for the character of Buffy Summers (Sarah Michelle Gellar) and her Slayerettes (or “Scooby Gang,” as they’re best known). But when it comes to love-hate—and the epitome of enemies-to-lovers—only one character truly could get under the Slayer’s skin: Spike (James Marsters), a platinum-blond vampire with warped ideas about love. (Okay, technically, Faith The Vampire Slayer could also be argued as a love-hate relationship for Buffy, but for the purposes of this piece, the non-canon nature of the pairing as a will-they/won’t-they disqualifies it.)
Despite the whole “Vampire Slayer” thing, Buffy Summers was obviously not immune to their charms. In the case of her relationship with Angel, that came with the caveat that he was a vampire with a soul—as close to a “righteous man” as one could be. Spike, on the other hand, would be introduced in the second season as an antagonist hellbent on killing Buffy (as that would make her the third Slayer he’d murder in his 100-plus-year unlife). From the moment Spike sees Buffy, he’s clearly drawn to her and even more fascinated by the fact that this is a Slayer with friends and a family. Of course, that fascination still comes from a place of wanting to end her—especially to help his beloved fellow vampire and gothic better half, Drusilla—but by the end of his introductory season, he’s teaming up with Buffy to stop Angelus (a now-soulless Angel) from bringing forth the end of the world and taking Drusilla away from him.
Spike returns for a guest spot in the third season, forcing Buffy and a re-ensouled Angel to reevaluate their relationship before returning in the fourth season as a series regular and foil for (as well as reluctant member of) the Scooby Gang. (He becomes “neutered” by a military-grade chip that prevents him from harming humans.) A spell-gone-wrong in the eighth episode of that season sees Buffy and Spike fall in love and become “that” couple (full of PDA, constantly breaking up to make up, and vice versa), essentially poking fun at the Buffy fans who had already started to latch onto the idea of “SPUFFY.” (Once the spell ends, Buffy and Spike are both immediately and thoroughly disgusted by the fact that their lips ever touched.)
Early in the fifth season, Spike realizes he’s developed feelings for Buffy, starting with a mortifying dream that leads to an obsession that goes from role-playing scenarios with himself and Buffy, making a Buffy mannequin, and then commissioning a Buffy sex robot. However, as Spike’s feelings for Buffy become apparent to her and the gang, as disgusted as they are by it, they also seemingly become realer. Buffy goes from calling Spike “beneath” her to throwing him a bone and kissing him for the punishment he endured to protect her family. And when Buffy (spoiler alert) dies in the fifth-season finale, Spike is visibly heartbroken, the same as everyone else in Buffy’s life.
But it’s the controversial sixth season of the series that truly fulfills the enemies-to-lovers promise of this relationship, as Buffy is brought back to life and finds herself struggling with depression, bills, and general ennui. In this state, Buffy ends up turning to Spike, and the two finally engage in an aggressive, sadomasochistic sexual relationship throughout the season. This is not the epic romance of Buffy/Angel, treated as true love despite the Slayer/vampire pairing. It’s sordid, with Buffy and Spike literally having sex in a rundown house with massive structural damage (some they caused, some that was already there) or behind a fast-food dumpster. And as Buffy makes clear, it’s not love, even though Spike considers it to be on his end (despite not having a soul). But things take a turn for the worse as the season ends with Spike—again, soulless—attempting to rape Buffy, trying to force her to “feel” what they had again just as she is attempting to bounce back from her depression.
Spike then drives a motorcycle to Africa to rectify his actions, setting out to get his soul and finally be the man who Buffy deserves. Still, Buffy and Spike do not end up happily ever after, with Buffy telling a self-sacrificing, dying (he gets better) Spike in the series finale that she loves him—and Spike telling her she doesn’t but he appreciates the gesture anyway. Buffy/Spike was definitely not a typical boyfriend-girlfriend pairing, but that never stopped fans from being invested in this love-hate, enemies-to-lovers relationship, a dynamic that propelled the Spike character from villain with a shelf life to the series’ romantic leading man.
Gossip Girl (six seasons, 2007-2012)
As far as the complicated nature of designating a lot of these specific pairings into the correct subgenre of will-they/won’t-they, things get extremely complex with teen dramas. (In Buffy the Vampire Slayer, while Buffy/Spike was the obviously enemies-to-lovers scenario, technically Xander/Cordelia also could’ve held a spot as a love-hate situation.) Basically, with a teen drama, everyone’s fucking, so what even counts as a “will-they/won’t-they” or an “after all these years” or a “coming-of-age” or a “love-hate”? Is it simply just hooking up because of teenage hormones? Ultimately, it all boils down to what the show (and, to an extent, its fandom) considers the formative romance (or romances) of the series.
So, unfortunately for the dozens of “DAIR” fans, Dan Humphrey/Blair Waldorf was not considered the formative romance of the series. They do, though, fit the bill of a love-hate, enemies-to-lovers situation. Dozens latched onto that earnest Dan/Blair stairwell scene in the series’ fourth episode, after Dan overhears Blair confronting Serena van der Woodseen about her issues with her best friend. This essentially humanizes the show’s mean girl, not it girl—and in front of the fish-out-of-water character who found himself antagonized by the former and enthralled by the latter.
As Dan continued his on-again, off-again will-they/won’t-they relationship with Serena throughout the series—and Blair, likewise, with Chuck Bass—he and Blair barely tolerate each other, both seeing the other as necessary evils in their respective relationships with Serena. The begrudging tolerance became a begrudging friendship once they both reached NYU in the third season—and grew even more in the fourth once they realized they actually had a lot of interests in common (to the point Blair even considers Dan her intellectual equal). The pair even ended up as interns at the same magazine—and got fired after their patented petty squabbling. However, from there, their bond actually grows stronger, and they realize they might have romantic feelings for one another. While the kiss makes Dan realize he has them for Blair, it only reaffirms hers for Chuck (and Dan keeps his thoughts to himself).
Dan and Blair finally get together in the fifth season (after some classic Gossip Girl subterfuge), when Blair is torn between her love for Chuck and a Monégasque prince. But despite going through romantic-relationship firsts and Dan confessing his love for her (and offering to spend the summer in Italy together), all roads lead back to Chuck for Blair. The sixth and final season sees a bitter Dan angry that Blair has left him for Chuck (though, all roads also led to more Chuck-and-Blair drama) and turning his back on the rest of their friend group. But Dan eventually acquiesces to their relationship, and the series ends with a Chuck/Blair wedding and then a Dan/Serena wedding (at Chuck/Blair’s apartment). It essentially undoes the past couple of seasons of character development between Dan and Blair (both separately and together), and it left much to be desired for plenty of pockets of the series fandom, not just specific ‘shippers. But despite that undoing, Dan/Blair did still happen and provided plenty of lasting moments for love-hate will-they/won’t-they devotees.
Killing Eve (four seasons, 2018-2022)
The question for Eve Polastri (Sandra Oh) and Villanelle (Jodie Comer) wasn’t so much “will they end up hooking up?” as it was “will they end up murdering each other?” But to be fair, the answer by the end of the series wound up being “they will” on both fronts. (Fun for all, right?) That said, even viewers who wanted those answers ultimately ended up being disappointed in the execution.
Created by Phoebe Waller-Bridge, who served as the head writer for the first season (followed by Emerald Fennell, Suzanne Heathcote, and Laura Neal in subsequent seasons) and based on Luke Jennins’ Villanelle novel series, Killing Eve was a cat-and-mouse tale between intelligence operative Eve and unhinged assassin Villanelle. The latter quickly found herself attracted to the former, and both women became obsessed with the other. While Villanelle’s infatuation with Eve was explicitly made sexual in the first season, Eve’s wasn’t necessarily portrayed as such, despite the pair’s will-they/won’t-they energy. Instead, the obsession seemed to stem from an emptiness in Eve’s life. Think pieces about the show at the time spoke of the “queer ambiguity” of Killing Eve, under the assumption that the series would never make any romantic aspect of the series anything but one-sided. And the “nice” moment the two end up sharing at the end of the first season is cut short by Eve stabbing Villanelle and Villanelle fleeing.
Eve and Villanelle continue to be consumed with each other in their own ways, with Eve spiraling (and destroying her personal and professional lives in the process) and Villanelle having a reason to continue stalking Eve, as she’s tasked with living up to the show’s title. It all culminates in Villanelle trying to get Eve to continue down a dark path that will make them the same. But Eve doesn’t fully go down the rabbit hole and also rejects Villanelle when she tells her she loves her…so Villanelle shoots her and leaves her for dead. (If nothing else, no one can say Killing Eve didn’t deliver on the “enemies” part of “enemies-to-lovers.”)
Villanelle spends a portion of the third season believing she did kill Eve and tries to move on—but that’s all for naught once she discovers her beloved is still alive. So Villanelle continues to pursue Eve, sending her presents and messages, as if the attempted murder was just a lover’s spat. The two end up finding each other and fighting on a bus, in a moment where Eve turns the tables by kissing Villanelle before headbutting her. The season ends with the two discussing their future together, or lack thereof. It’s a far cry from the ambiguity and subtext of the first season, even as the two walk away from each other to end it all.
In the final season, Villanelle tries to prove to Eve that she’s changed and is no longer trying to make Eve more like her. But there is no happy ending—until the series finale, when the two finally do end up running off together, romantically entwined…only for Villanelle to die, saving Eve’s life. (On a metaphorical level, Eve had definitely been “killed” by then.) Again, the series definitely answered the will-they/won’t-they question with “they will.” But by that point, interest in Killing Eve had seriously waned, and even those who wanted Eve/Villanelle to get together were disappointed. Compounded by the creative turnover from season to season, the execution of Eve/Villanelle was proof that not every will-they/won’t-they should. But all of these examples do serve as reminders that there are plenty of ways to make the love-hate/enemies-to-lovers scenario work—and just as many to completely bungle them.
Next time: Coming of age (a.k.a. will-they/won’t-they situations in teen shows)
