Random Pop Culture Top 10 List
Best Will They/Won't Theys
Jordan & Rachel
Random Pop Culture Top 10 List is a (fairly self-explanatory) biweekly list in which the Review to be named gang take stock of the realm of pop culture, and come up with their Top Ten in a specific category.

Top Ten Will-They-Won't-They's:

There is nothing more wonderfully frustrating, more delightfully obnoxious, than a well-crafted will they/won't they relationship. The back and forth, the dreams deferred, when done properly, are enough to keep us coming back for more. Here is a list of our favorite will they/won't they pairs, the ones that have us wrapped around their fingers.

Special note from Jordan: THIS LIST IS SPOILERTASTIC. Consider yourself forewarned.

10. JD and Elliott, Scrubs

JD was always kind of a mess of a character, and more than a bit of a jerk. Elliott was insecure and kind of unstable. They did terrible things to each other, yet they made each other happier than anyone else. Sure, their will-they-won't-they dragged on a bit in later seasons (where the show took to parodying the nature of the relationship by comparing JD and Elliott's on-again-off-again romance to the steamy trials of Dr. Ross from radiology and Rachel, the nurse he loved), yet the show always managed to find an emotional center to their relationship that made sense and kept the dynamic solid, even as the rest of the series took a dive, quality-wise. They were trailblazers in that the show wasn't afraid to put them together in the first season (in one of the all-time best episodes, "My Bed Banter and Beyond"), which considering their high stress jobs, total lack of social lives, and chemistry, was a completely realistic development. The show was bold enough to show us why these two were horrible together and why they couldn't work out. JD was immature and selfish, Elliott was insecure and terrified of being hurt. Yet they relapsed time and again over the course of the series because something drew them together, even if they didn't really work. This never felt like the writers struggling to imbue the relationship with tension; it just existed naturally, and no contrivances were needed to keep them apart. They handled that just fine by themselves. The two matured over the course of the series until they were able to be together without destroying each other, and in fact, be perfect together. From their first meeting, in which JD saves Elliott from a tough question in rounds, only to show his immediate attraction to her and allow her the upper hand to JD's big declaration of his love in the final season (the show ended after Season 8. We don't care what any of you say about some fictional "Season 9."), they were a bit of a mess, but the kind you can't help but root for anyway. Plus, these two were so screwed up, they couldn't possibly be with anyone else.

9. Niles and Daphne, Frasier

Niles Crane is potentially the most eccentrically lovable character in sitcom history. He's twitchy and nerdy and likes opera and art and he sort of looks like a bird. But he's also adorable and funny and sensitive and desperately in love with Daphne Moon, his father's homecare nurse. Daphne is crass and uncouth and brazen; she enjoys simple pleasures and has a generally unrefined tastes. But this is one of the many classic will they/won't theys that hinge on the fact that opposites attract. It seems a simple enough equation, but it takes these two love birds an awfully long time to finally figure it out. For years (and years and years and years) Niles pines from afar while two of his marriages deteriorate, and it isn't until Daphne prepares to walk down the aisle that he finally gets up the nerve to tell her how he feels. The show played with the tension between these two so well, the slow boil (they don't get together until the season seven finale!) barely ever irked, and there interactions were malleable enough that the show could do jokes about how obvious Niles was and how oblivious to his love Daphne was one week, and have the two dance dangerously close to working out (like in two of the show's best episodes, "Daphne Hates Sherry" and "The Ski Lodge") the next without the situation ever feeling contrived or forced. And once they got together, somehow, their interactions just got better. This was one will-they-won't-they that aged like a fine wine Niles would have raved about to Frasier. Daphne endearingly cuts Niles' intense pretension, and the hijinks that ensue from Niles' flamboyant snark and repressed emotions meeting with Daphne's homespun sincerity secures their spot on this list.

8. Booth and Brennan, Bones

Bones is not your typical crime procedural. Sure, there are fancy machines and x-rays and that weird spray that makes blood shine like neon. But at its core, Bones is really just about a group of super intelligent, lovable nerds. And at the center of that group are Booth and Brennan. Bones does at great job of spreading this relationship out in a way that doesn't seem overly contrived. It carefully unwinds Booth and Brennan's history, builds their partnership and creates a connection between these two unlikely friends. First professionalism, then other relationships, stand in their way, but all the while the connection between these two, one based in trust that comes from trying not to get killed together on a regular basis, is palpable. Both profess their feelings for each other, but never at the same time, and never in a way that would work. But the "will they/won't they" tango took a radical turn at the close of season 6, when Brennan discovers she's pregnant and Booth is the father, because they'd start a relationship on the down low after an office tragedy made them realize what actually matters, in a move that acknowledges six seasons of slow burn with a big bang.

7. Tim and Dawn, The Office (UK)

On a show that was never afraid to be realistic, even if that meant if was cripplingly depressing just as often as it was hilarious (if not for the Christmas Special, this show might have been memorialized as having the biggest downer ending in the history of television), Tim and Dawn were developed as the most realistic will-they-won't-they in television history. Tim nurses an office crush on the one person who understands how absurd their environment is (and is willing to help him mess with Garreth), but Dawn is perpetually engaged, and eventually moves to the U.S. with her fiance. Without her, Tim soldiers on, and without him, she lets her dream of being an artist lapse for more realistic concerns. This is the way that life is sometimes, and its sad, but it makes perfect sense. However, when Dawn returns for the office Christmas Party, she gets a secret Santa gift from Tim: an oil painting set and a note saying "Never give up." And with that, she knows who she really should be spending her nights with. Their relationship, even at its climactic resolution is low key; no big speeches are needed, and grand gestures are set aside in favor of a quiet man pining from afar and giving the woman he loves the support she needs, even if it takes her a while to realize it.

6. Doug and Patty, Doug

O Doug Funnie. Maybe Doug is where so many RTBN staffers learned how to pine. The preteen harbors a serious crush for fellow Bluffingtonian Patti Mayonnaise, the delightful orange girl with the southern-esque accent and easy going personality. Outgoing, athletic Patti is a perfect counterpoint for the introverted, imaginative Doug, and Doug spends several seasons writing about her in his journal and attempting to avoid being permanently friend-zoned. Patti's dads wedding in the series finale is the perfect setting for Patti and Doug to decide to take their relationship to the next level and go out on a "date date," capping off a sweet adolescent love story that's stuck with us.

5. Tim and Tyra, Friday Night Lights

Most of Friday Night Lights is a heartbreaking will they/won't they, romantic and otherwise. Will the Panthers win? Will Coach Taylor move up to the college level? Will Tim Riggins take his shirt off this episode? Considering the show is about high school, there are a lot of relationships that start with some pining and end in some kind of catastrophe, but none is as moving as the series long on again/off again entanglement between Tim and Tyra Collette. What makes this relationship so compelling is the growth both of these characters go through over the course of the series. Tyra starts as a punk-ass little floozy to Tim's womanizing deadbeat heart throb. But with every episode the emotional nuance in these characters becomes more and more pronounced. They're together, they break up, they get back together, they break up, they find their way back to each other. But the will they/won't they doesn't seem like a game here. It's more that both of these characters have a lot of growing up to do, and the only real way for them to do that growing up properly is to put their relationship on the back burner. As volatile as their relationship starts out as, by the end we see that years of shared beds and shared feelings have made these two really good friends. Tim goes through a lot of shit in his life, and the final recognition of his feelings for Tyra, and her feelings for him, seems like a good way for Tim to get what he deserves: someone who loves him for who he is. And hey, Tyra isn't Minka Kelly, so that makes her worth rooting for.

4. Nate and Brenda, Six Feet Under

The format of a hyper-intellectual woman and a working class cad will make another appearance higher on this list, but Nate and Brenda earn a special place if for no other reason than their volatility. The two break up and get back together multiple times throughout the run of the series, largely due to their emotional failings and tendency to self-destruct, yet they are always there for each other in their times of need. Nate meets Brenda just hours before he learns his father has died, and over the course of the series, the two help each other through multiple deaths (including her father and his first wife, Lisa) as Brenda tries to help Nate come to terms with his own mortality and Nate tried to help Brenda tear down the walls she has built up around herself after a childhood spent as the focus of a psychological study on prodigies (and after being raised by two therapist parents). Nate and Brenda are a great will-they-won't-they because there are valid arguments on both sides of the equation: the two are terrible for each other, but they also understand each other better than anyone else. The two are headed for divorce when (SPOILER ALERT) Nate dies in the show's fifth season, yet had he survived, we are sure they would have ended up back together (probably before breaking up and getting back together again). They just can't help themselves.

3. George Michael and Maeby, Arrested Development

Arrested Development never had to worry that the contrivance keeping George Michael and Maeby apart would be seen as too ridiculous. After all, they were cousins. It's not a surprise that the greatest sitcom of all time managed to turn in one of the best will-they-won't-theys ever, but it is kind of shocking how easily the show got its fanbase to root for incest. George Michael was shy, dutiful, and woefully moral. Maeby was outgoing, rebellious, and willing to do whatever it took to get what she wanted (including pretending to be her own terminally ill twin sister or faking her way into a job as a movie studio executive basically only due to her use of the phrase "Marry Me" whenever someone questioned her age). At first, it seemed as if George Michael was doomed to harbor a one-sided crush forever, but eventually, Maeby began to warm to the idea, and the two shared a kiss as the house literally collapsed around them. In the series finale, it was revealed that Maeby is not actually related to George Michael, giving new hope to the idea that these two crazy kids might make it work. Yet George Michael resigns himself to the fact that whether or not they are related by blood, Maeby is his family, and that is more important than any fleeting teenage romance. At least until the new season starts sometime in 2013...

2. Josh and Donna, The West Wing

There wasn't a chance in hell this list was going to come to press without an appearance by a Sorkin creation. There's really nothing more adorable than banter, and when mixed with the emotional nuance of nearly every Sorkin character, it's a surefire recipe for will they/won't they success. Josh and Donna make the list for the completely unforced way their relationships unwinds, the strong connection that is made blatantly clear years before the pieces finally come together for them, the loyalty and trust they have for each other, the way they aren't afraid to attack each other. Even as other romantic interests breeze in and out of Josh and Donna's personal lives, we always know that at the end of the day, Josh will have Donna and Donna will have Josh. It's particularly endearing that when the relationship finally materializes, Josh proves to be his completely awkward self, as if the nearly ten years he's known Donna have gone completely out the window. These two are perfect, their relationship is never leveraged as a stunt, and they manage to stay true to form as friends and lovers.

1. Sam and Diane, Cheers

The original will-they-won't-they is still the best, without a doubt. Sam and Diane's relationship was orchestrated perfectly from the pilot, in which Sam is surprised by his attraction to the girl at the bar and offers her a job. The show waited just long enough to put them together, teasing out their sexual tension and screwball banter throughout the first season before the two finally decide to do it in the finale. Yet their relationship was never without its problems (hell, most of the attraction came from the fire these two created in their constant sparring), and they were driven apart by their differences at the end of season two. The show managed to put blocks between them that were entertaining and realistic enough to withstand any attacks on their credulity (the best of these blocks, Diane's relationship with Frasier Crane, ended up working so well that Frasier stuck around for the entire rest of the series and for his similarly long-lived spin-off, which we mentioned above), but eventually the two were bound to get back together, with Sam proposing to Diane at the end of the show's fourth season. It wasn't meant to last, of course, as Diane left Cheers to go work on a book, promising to return in six months to marry Sam. Their relationship was so perfectly played, the show managed to give them a bittersweet ending that serves as a utopian ideal of "it just wasn't meant to be" not once, but twice. When Diane leaves the first time, she promises to return, and Sam smiles sadly and says "Have a nice life." And when she returns in the show's series finale, the two prepare to run off to California together, until Sam realizes that his one true love is Cheers. Sometimes the best will-they-won't-theys are the ones that just aren't meant to be, and it takes a show of great emotional intelligence and, yes, bravery to let us know that things don't always work out in the end.

Honorable Mentions


Roger and Joan, Mad Men

I don't care what Jordan says, Roger and Joan are perfect. They're hot, they're honest (with each other, at least most of the time), and I can't wait for Joan to have a little silver-fox baby.

Veronica and Logan, Veronica Mars

Like any good "will they/won't they" Veronica and Logan start their series-long flirtation by hating each other. They're dark and twisty and damaged and I love it.


JD and Turk, Scrubs

Sure, JD and Elliott are the ones who date, but the real romance on this show is undoubtedly between Best Friends JD and Turk. This only doesn't make the list because there's no will-they-won't-they here. These two have "Guy Love" from beginning to end.

Wesley and Fred, Angel

Mal and Inara are great, but short lived. The real Whedon triumph is the slow burn of Wesley and Fred, who spend seasons circling each other, finally getting together all-too-briefly before tragedy tears them apart.

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