The 20 most heart-wrenching will-they-won’t-they couples in TV history

Ross and Rachel are the ultimate will-they-won’t-they couple. It took the entire series of Friends to know whether they would or they wouldn’t, and the end to their story (at least what the audience got to see) was totally worth the wait. 

There’s something so fun about a will-they-won’t-they couple in high school. The O.C.’s Seth and Summer simply going to school together made their forced proximity totally natural, and it made for some great episodes in their won’t-they phases. 

Jake and Amy were the heart of Brooklyn Nine-Nine for its entire run. Even after it was clear they were going to be together for the rest of the series, they were just as sweet to watch. They were a couple the audience was always rooting for. 

Though Abbott Elementary is still (hopefully) early in its run, Janine and Gregory are one of the best will-they-won’t-they couples in TV history. Their chemistry is unreal, and their interactions aren’t at all contrived. They’re a delight to watch on screen.  

Will-they-won’t-they couples can’t be discussed without mentioning Jim and Pam. The couple was magnetic from the start, and their will-they-won’t-they, albeit frustratingly, kept up a bit even after they were married, showing how commitment doesn’t stop just because a couple has exchanged vows. 

Jim and Pam, rightfully so, get loads of attention for their will-they-won’t-they storyline, but Dwight and Angela deserve some love, too. Their relationship is far more twisted and dramatic, and they keep audiences invested in their romance for the entire series. 

Jess and Nick are a great will-they-won’t-they couple because they are so obviously meant to be. They each have other partners that provide plenty of entertainment value during New Girl, but in the end, it’s Jess and Nick for life. 

All the best sitcoms have two will-they-won’t-they couples. Cece and Schmidt’s will-they-won’t-they starts and ends before Jess and Nick’s, and because it runs on a completely different timeline, it acts as the perfect complement. It’s also incredibly entertaining in its own right.  

What’s so great about Leslie and Ben as a will-they-won’t-they couple is that neither of them seem like will-they-won’t-they people. They’re measured and honest people, but their circumstances make things difficult. It’s unexpected, and so, so great. 

You know you’re an iconic will-they-won’t-they couple when your love story ends in tragedy, and you’re still beloved. Such was the unfortunate fate of Meredith and Derek on Grey’s Anatomy. Tragedy aside, these two were great together. 

Luke and Lorelai are one of the most frustrating will-they-won’t-they couples in all of television, but that doesn’t make them any less great. They’re so good together, and their good moments outweigh all of the bad. They’re some of the best that Gilmore Girls has to offer. 

Watching Jane and Rafael’s will-they-won’t-they storyline play out on Jane the Virgin was also somewhat maddening, especially considering they both had another will-they-won’t-they partner. And even when their path to be together was seemingly clear, obstacles still arose. But it was all okay in the end. 

Gossip Girl wouldn’t be Gossip Girl without Blair and Chuck, and Blair and Chuck wouldn’t be Blair and Chuck without their will-they-won’t-they romance. Though both dark and twisted, Blair and Chuck had a soft spot for the other. It was always them. 

How I Met Your Mother’s Marshall and Lily are a classic will-they-won’t-they couple. They’re truly in love, the reasons that are keeping them apart seem so simple to solve, and it’s so satisfying when they finally get together for good. 

We love a will-they-won’t-they that’s set up from the very beginning, just like it was for Jonah and Amy at the start of Superstore. Jonah and Amy were sweet and entertaining, and one of those couples who were always a couple, even when they weren’t together. 

Cory and Topanga’s will-they-won’t-they romance started very early in life. While some Boy Meets World viewers might think the two should’ve gone their separate ways as adults, as a television couple, their history only made their relationship that much sweeter and easier to root for. 

Will-they-won’t-they couples are far more dramatic in dramas than in sitcoms. Obvious, yes, but it can also make for couples who aren’t together for ridiculous reasons. Harvey and Donna aren’t, for the most part, like that, though. They’re the Suits couple that should’ve been together all along and are great together when they finally give in. 

The writing was on the wall with Fran and Mr. Sheffield. Their feelings for each other just needed to catch up with what the audience was hoping for. When Fran and Mr. Sheffield are at their best, The Nanny is at its best. 

Niles and Daphne have one of the most hilarious will-they-won’t-they relationships in all of television. Between Niles’ elusive wife — who’s never actually seen on an episode of Frasier — and his somewhat painful interactions with Daphne, Niles makes this romance wholly entertaining from start to finish. 

It may be controversial, but Carrie and Big are absolutely one of the best will-they-won’t-they couples of all time. Sex and the City wouldn’t be the same show without their relationship. And while they both had obvious red flags, they couldn’t stay away from each other.