7 Greatest "Will They Won't They" TV Romances, From 'Friends' To 'The Office'

On the whole, we’re a society that loves romance. We like to see people bind together, pledging devotion and compassion, trading intimacies and expressions of appreciation that might never be found beyond the walls of their union. But as much as we do love this whole ordeal, we’re not willing to hand a happy ending over to just about anyone. You have to earn it. Not by proving yourself valiant and whole of heart, but by trudging through months — no, years — of contention, misery, angst, ennui, and any other variation on plain ol’ bummed out-ness that you can muster. Oh, and hijinks. There must be hijinks. Just ask Ross and Rachel from Friends.

And once you and your would-be partner are steeped almost irreparably in what seems like a never ending typhoon of dejection and agony, pining ceaselessly for one another but constantly pushing each other away, then you’ll be worthy of one another’s love, as well as our attention. You’ll be what we call a “Will They Won’t They,” the greatest sort of romantic epic known to modern humankind. 

We’ve seen lots of WTWTs (not established shorthand) over the years, all fostering their own personal brand. There’s the “He Loves Her and She Doesn’t Even Know It, But Do You Think They’ll End Up Together?” type, the “They Slept Together Once and Both Agreed Just to Be Friends, But Do You Think They’ll End Up Together?” type, the “They’re Both in Relationships But You Can Tell That Their True Feelings Are for One Another, So Do You Think They’ll End Up Together?” type… among others.

So let’s take a moment to look back upon these emotional blitzkriegs and determine which among them is the truest, most romantic, most volatile, most uncertain “Will They Won’t They” of all.

Ross and Rachel

Parties Involved: Ross Eustace Geller and Rachel Karen Green

From: Friends

“Will They Won’t They” type: “They Dated, He Messed Up, They Broke Up, Rinse, Repeat, But I Think They’ll End Up Together”

Lasted for: Ten long, arduous, baby-laden seasons

Until: They ended up together

Assessment: Friends seems to think that its central love affair is the kingpin of this trope in popular culture. Then again, he made a list about her flaws, slept with the girl from the copy place, lied to her about annulling their drunken Vegas wedding, and got all high-pitchy all the time, so I kind of stopped rooting for those two after a while.

J.D. and Elliot

Parties Involved: Dr. John Michael “J.D.” Dorian and Dr. Elliot Reid

From: Scrubs

“Will They Won’t They” type: “They Dated Briefly and then Broke Up, But Have Indicated Interest Sporadically Ever Since, and I Think They’ll End Up Together”

Lasted for: Eight seasons, although most of us had kind of tuned out by the sixth

Until: A particularly anticlimactic reveal that they’re dating again, and will ultimately end up married

Assessment: One of the poorer executions of the trope, especially for such a likable show, perhaps considering the fact that creator Bill Lawrence never wanted them to end up together and intentionally drove them apart early in order to kill the possibility. Oh, how little he knew then of American television.

Ted and Robin

Parties Involved: Theodore Evelyn Mosby and Robin Charles Scherbatsky

From: How I Met Your Mother

“Will They Won’t They” type: “We Already Know for Certain That He Doesn’t End Up with Her, But I Still Think They They’ll End Up Together”

Lasted for: Nine seasons of painstaking deceit, and a decade and a half of epilogue

Until: Somehow, against all odds and reason and common decency, they do end up together

Assessment: Even the Internet was unprepared for the rage incurred by this union.

The Nanny and Mr. Sheffield

Parties Involved: Francine Joy Fine and Maxwell Beverly Sheffield

From: The Nanny

“Will They Won’t They” type: “She Works for Him, So It’d Be Kinda Awkward! But Yeah, They Will 100% End Up Together”

Lasted for: Three seasons until he said he loved her, then another until he admitted he said he loved her, then one more until they were together, and then a few more until they were engaged… or, wait, is that right? Let’s start over…

Until: Eh, whatever, they end up together

Assessment: One of the few examples that didn’t rob the show of too much of its humor, as the odd couple dynamic remained throughout their likewise hijinks-infused steady relationship.

Jim and Pam

Parties Involved: James Halpert and Pamela Beesley

From: The Office

“Will They Won’t They” type: “I Guess We’re Supposed to Root for These Two to Get Together, Since They’re the Only Young and Pretty People Around, Plus the Camera Keeps Diverting to Them, So, Yeah, I Think They’ll End Up Together”

Lasted for: Three full seasons of flirtation

Until: They began their courtship and the life force of The Office died on impact

Assessment: Without question the most boring and chemically deficient romance that the American public ever cared so arduously about. (And we did. We all did. We still care.)

Lorelai and Luke

Parties Involved: Lorelai Victoria Gilmore and Lucas Danes

From: Gilmore Girls

“Will They Won’t They” type: “She Likes Coffee and He’s Always Telling Her to Drink Tea, But I Think They’ll End Up Together”

Lasted for: Just over four seasons until their relationship begins in earnest, and then another one until they get engaged, another one until they break up, and one more…

Until: …they kiss, insinuating that they will indeed end up together

Assessment: Things were going just fine the writers went hog wild and roped in Lorelai’s ex-husband to complicate matters. And by complicate matters, I mean he really had a way of undercutting what was on the whole an honest and earthy relationship.

Sam and Diane

Parties Involved: Samuel Malone and Diane Chambers

From: Cheers

“Will They Won’t They” type: “God, They Absolutely Hate Each Other! …But I Think They’ll End Up Together”

Lasted for: Six seasons of yelling, insulting, slapping, chasing each other to Europe, and ruining poor Frasier’s life

Until: They did not end up together! In a huge reversal of theme, Diane leaves Sam at the altar at the very last minute (confirming his suspicions that she might) and jets off to Hollywood, not to return for another six years… when, once again despite their mutual feelings for one another, they do not end up together

Assessment: The true great sitcom love story, picture perfect ending or no. Sam and Diane could not have been more different, and were rattled to the core and at times disgusted by their attraction to one another. That they never tied the knot is the best testament to their brand of romance: Love is illogical, chaotic, and occasionally toxic. It rarely makes sense and frequently doesn’t work out. But that doesn’t mean it isn’t worthwhile.

Images: NBC (4); CBS (2); WB

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