Five Will-They-or-Won’t-They Sitcom Relationships That Became Exhausting

The will-they-or-won’t-they relationship has been around long before sitcoms were even a thing, and though it can prove fruitful comedically, it also has its many pitfalls. If the characters don’t end up together, the audience isn’t satisfied (like Frasier), and often a dramatic tension. As a result, many sitcoms try to drag out the will-they-or-won’t-they dynamic for as long as possible, which can end up being so tiresome that most viewers are ready for a won’t they.
Here are four shows that tried to keep their will-they-or-won’t-they relationships going way beyond their expiration date…
Ross and Rachel on ‘Friends’
Ross’ feelings for Rachel (Jennifer Aniston) are introduced in the very first episode of Friends, but they don’t get together until well into Season Two. They then “take a break” near the end of Season Three, during which Ross (David Schwimmer) sleeps with someone else whereas Rachel decides she wants to get back together. Season Four begins with them reuniting, then breaking up again right away. Ross gets a new girlfriend, they get engaged and Rachel breaks up the wedding at the end of Season Four. Ross and Rachel then get married at the end of Season Five while drunk and get divorced by Season Six. Ross and Rachel stay broken up until it’s revealed that Rachel is pregnant with Ross’ baby in Season Eight — the same season that romance develops between Rachel and Joey (Matt LeBlanc) — and it’s not until the end of Season 10 that Ross and Rachel, who everyone wanted to see together since episode one, finally end up together.
Although all the “We were on a break!” stuff is Friends nostalgia at its finest, the constant back-and-forth between Ross and Rachel manufactured by the writers eventually wore out even the most loyal of fans. Once they got drunkenly married in Season Five, many felt like they should have stayed together and found their divorce downright depressing. And fans still get angry when you bring up the Rachel and Joey romance. At a certain point, all the twists and turns feel as annoyingly unbelievable as the size of their New York apartments.
Tony and Angela on ‘Who’s the Boss?’
From the start of Who’s the Boss?, advertising executive Angela Bower (Judith Light) shares a mutual attraction with her live-in housekeeper Tony Micelli (Tony Danza), but it takes a very long time for the show to deliver. Despite drunkenly kissing at the end of Season One, it takes until the eighth and final season for them to finally get together. The two get engaged, and naturally, fans wanted a wedding to cap off the series. Instead, they were left with an ambiguous ending that frustrates them to this day.
J.D. and Elliot on ‘Scrubs’
After meeting in the pilot and sleeping together later in Season One, J.D. (Zach Braff) and Elliot (Sarah Chalke) don’t waste a lot of time in the pre-relationship phase — something most other sitcoms on this list explore… and explore… and explore. However, after their initial hook-up, they soon break up in a pattern that will repeat itself until Season Three. Then, Elliot gets a new love interest in Sean Kelly (Scott Foley), and J.D. breaks them up only to realize that he actually doesn’t love Elliot anymore. For the next five years, J.D. and Elliot aren’t romantically involved, and the show’s decision to take a break from the push-and-pull of their relationship is a relief. That said, many fans were still clamoring for them to get back together, and in Season Eight, they finally do.
In Season Nine — the much-maligned Scrubs: Med School season — it’s confirmed that they’re now married and expecting a child. In the end, the show got it right, but many fans still think it took too long. In interviews, creator Bill Lawrence said he didn’t want a will-they-or-won’t-they thing between the two, which is why he killed the relationship in Season Three, but his aversion to the dynamic may also have prevented the audience from getting what they ultimately wanted.
Kevin and Winnie on ‘The Wonder Years’
The Wonder Years begins with Kevin Arnold (Fred Savage) and Winnie Cooper (Danica McKeller) kissing for the very first time. While this moment was also the first-ever kiss for both of them separately, it’s a one-off for them together, and they eventually pursue relationships with other people, not kissing a second time until the end of Season Two. They don’t become a couple until well into Season Three, then they break up a few episodes later. They go back and forth like this until the end of Season Six (the final season) when it’s implied they lose their virginity in the finale.
Still, in the narration from the future, Kevin reveals that the two don’t end up together, disappointing basically anyone who ever watched the show.
Niles and Daphne on ‘Frasier’
When Frasier begins, Niles is still married and his infatuation with his father’s physical therapist is ripe for humor, allowing David Hyde Pierce to play the beats of a schoolboy crush while Jane Leeves’ Daphne gets to be clueless about the attraction. This lasts until Season Three, when Niles gets divorced, but the writers didn’t want to rush into a relationship between Niles and Daphne, so they jerk them both around a bit by putting them both in various relationships absolutely no one cared about. Niles even gets married (and divorced) again. It isn’t until the end of Season Seven that they finally end up together, when Niles, after learning Daphne also harbors feelings for him, breaks up her wedding to another man.
Their union was both good and bad for the series. Yes, fans were happy to finally see them together, but the show also lost some of its spark. The characters were just funnier when they were miserable.