10 Will-They-Won't-They Romances That Went On Too Long

Over the years, there have been several will-they-won’t-theyTVromances that went on for far too long. Many of the best TV shows of all time teased a potential relationship between characters, which helped audiences invest in the story even more. Typically, the best will-they-won’t-they storylines were successful because the writers knew exactly when to wrap things up and provide a good payoff. However, not every couple was lucky enough to receive this treatment.

A will-they-won’t-they romance that went on for too long didn’t mean that the relationship was necessarily bad, though. Although the fact that some were ridiculously dragged out ruined the overall opinion of the characters, others just needed some time to grow and build tension, but they carried on for so long that it ruined the show’s pacing or simply frustrated audiences.

10 Dawson & Joey

Dawson's Creek (1998-2003)

The possibility of Dawson and Joey’s relationship was teased from the very beginning of Dawson’s Creek, and although they got together at the end of season 1, they later dated and broke up so many times it was hard to keep up. Joey’s romance with Pacey also caused a strange love triangle, too.

One of the moments that made Dawson’s Creek’s fans cry was when Joey admitted her feelings for Pacey, and the fact Dawson selflessly let her go only dragged out the will-they-won’t-they side of things. Although the childhood best friends to lovers storyline was endearing, it didn’t make the back and forth between Joey and Dawson any less irritating.

Dawson's Creek

Drama

10.0/10

Release Date: 1998-00-00 - 2003-00-00
Network: The WB
Directors: Greg Berlanti
Writers: Kevin Williamson, Greg Berlanti, tom kapinos

Cast

See All

James Van Der Beek
Katie Holmes

In the small town of Capeside, Massachusetts, fifteen-year-old Dawson Leery and his friends — tomboy Joey, class clown Pacey, and many more — experience the highs and lows of teenage life and coming of age.

Seasons: 6

The two frequently dated other people, then admitted their love for one another again, and even after a one-night stand in season 6, a flashforward to 2008 revealed that they were still just platonic. Dawson’s Creek’s original finale ending was initially going to see them get together again, but it was ultimately scrapped as production felt they were better off as friends.

9 Jane & Rafael

Jane The Virgin (2014-2019)

Although Jane the Virgin was heavily inspired by telenovelas, the will-they-won’t-they relationship between Jane and Rafael was rather over-the-top. From their initial meeting years before, to Jane’s pregnancy and through to Michael’s death, Rafael and Jane allowed far too many obstacles to get in their way, and most of the time, the only thing that was really stopping them from being together was each other.

The most frustrating thing, however, was that despite Jane the Virgin’s constant quotes about love and life, Jane especially couldn’t make her mind up about her feelings.

The most frustrating thing, however, was that despite Jane the Virgin’s constant quotes about love and life, Jane especially couldn’t make her mind up about her feelings. The on and off-ness of their relationship should have wrapped up when the pair settled down years after Michael’s death. However, Jane needed to see if there was still anything between her and her not-dead husband after it was revealed Michael was still alive.

Rafael then refused to entertain Jane when she returned from the ranch and realized she wanted to be with him, although this was totally understandable. It was wild Jane and Rafael made it up the aisle, and even though they got their happy ending, it was baffling that their will-they-won’t-they romance kept going that long.

8 Robin & Ted

How I Met Your Mother (2005-2014)

Robin and Ted’s relationship in How I Met Your Motherwas one of the most annoying will-they-won’t-they romances ever, which lingered from the pilot all the way to the finale. Audiences knew Ted would eventually meet Tracy, but this made his non-stop pining for Robin that much worse.

No matter what Robin said or did, like her frequently voicing she wanted different things in life, having other serious relationships, and getting married to Barney, Ted never stopped persevering. Even after Tracy died, Ted went back to his old ways. It was easy to relate to Marshall in every season of How I Met Your Mother, especially because he was vocal about the situation, and it pained him to see his best friend get his heart broken over and over again.

Ted admitted he was in love with Robin yet again on the beach just before her wedding, and it was shocking that writers still felt it necessary to keep pushing this narrative this late in the show’s run. Despite the ludicrousness of it all, Ted and Robin ended up together in the finale, although many were inherently against this.

7 Rachel & Ross

Friends (1994-2004)

Rachel and Ross were one of the most notable will-they-won’t-they romance in TV history, and although it was satisfying when they reunited in the Friends finale, the fact it had gone on for so long dampened the relationship storyline in general. Ross was in love with Rachel since they were in high school, and throughout all 10 seasons of Friends, both of them had feelings for the other at different points, which dragged it out massively.

Even when they had Emma, and Ross was going to propose, Friends still found a way to stop them from getting back together. Ross and Rachel’s relationship in Friendswas far more complicated than it ever needed to be, and realistically, they should have given up on reconciliation altogether.

However, viewers still rooted for them, despite the many stupid choices they both made. One of Friends’ most hated storylines was Rachel and Joey together, but this really served as a way to set up Ross and Rachel yet again. While it was a relief that Ross and Rachel finally sorted themselves out in the finale, it didn’t mean that Friends didn’t keep this story going far longer than it needed to.

6 Luke & Lorelai

Gilmore Girls & Gilmore Girls: A Year In The Life (2000-2007, 2016)

Gilmore Girls' Luke and Lorelai were a TV couple that took way too long to be together. The pair spent seasons 1 to 4 as just good friends, even though it was clear that there was more between them. Despite their other relationships during this time, they were somewhat patient, and after his divorce, Luke finally realized his feelings for Lorelai.

For some time, the pair were actually happy and were even engaged, but the unfinished business between Lorelai and Christopher threw a spanner in the works. However, it was unclear whether they’d ever reconcile. It was heartbreaking when Lorelai married Christopher while Luke focused on April, especially when audiences were so supportive of their love story.

After seven seasons of back and forth in Gilmore Girls, it wasn’t until the finale that they got back together. While it was an amazing moment and a huge relief when Lorelai and Luke’s relationship in Gilmore Girlspaid off and they finally married in Gilmore Girls: A Year in the Life, it was a shame it took that long for them to tie the knot.

5 J.D. & Elliot

Scrubs (2001-2010)

J.D. and Elliot’s relationship in Scrubsthankfully received a happy ending, but it was a long journey to get to that point. Their will-they-won’t-they storyline began halfway through season 1 after they sleep together, but by the end of the next episode, they ultimately decide to remain friends. Across the following seasons, there was a constant back and forth on J.D. and Elliot’s relationship status.

Elliot ended things with Sean to be with J.D. in season 3, only for Scrubs’ narrator to suddenly decide he wasn’t actually in love with her and break her heart. The two hooking up at least once a year was a common occurrence, and even the other Scrubs characters were fed up with how long this dragged out for.

It seemed their romance was over when J.D. met Kim, and even after they split and had Sammy, but Scrubs still reignited their love. They were far less dramatic after this, although this was mainly because a pregnant Elliot was barely in Scrubs season 9. Hopefully, the Scrubs revival will not reprise this part of J.D.’s story.

4 Sam & Diane

Cheers (1982-1993)

Just because Sam and Diane in Cheers were one of the greatest will-they-won't-they TV relationships of all time, this didn’t mean it didn't go on for too long. Their romance always lingered, even when Shelley Long’s Diane left Cheers in season 5’s finale. The pair broke up and got back together several times throughout the show, and Diane even left Frasier at the altar because of her unresolved feelings for Sam.

Diane and Sam were a great example of the opposites attract trope, but it didn’t make their on-off relationship status any less frustrating. However, Cheers subverted the will-they-won’t-they trope by ensuring the pair didn’t end up together.

When Diane returned just before Cheers ended, in the final episode “I Do, Adieu,” she and Sam attempted to rekindle their love and planned to leave Boston together. However, they ultimately decided against it. Although this was a great direction for the sitcom to take, it was strange that they did this, seeing as Diane leaving after getting engaged to Sam in season 5, only to disappear for years, was such a shock.

3 Andy & Erin

The Office (2005-2013)

Things were starting to look up for Andy Bernard when The Office introduced Erin Hannon in season 5. Andy had terrible luck with romances, especially when Angela had an affair with Dwight while they planned their wedding, and Erin seemed perfect for him. Although the pair dated for a short while, after their relationship ended, it was clear that they both still wanted each other.

This was despite their relationships with Jessica and Gabe, too, and while they both seemed happy for a while, Andy and Erin found a way back to each other. While Erin and Andy’s will-they-won’t-they romance didn’t go on for as long as others, it was still far too long. Erin leaving for Florida and Andy coming to get her and admitting his love, only to shortly after abandon his girlfriend on a long boat trip, was ultimately unnecessary.

Andy and Erin’s relationship in The Office never made sense, but their out of sync feelings for one another were the focus of the show’s later seasons. Compared to the likes of Dwight and Angela or Jim and Pam, they were a will-they-won’t-they couple The Office could have done without.

2 Jeff & Annie

Community (2009-2015)

While there have been many unpopular TV romances that eventually won viewers over, one that many could never get on board with was the one between Community’s Jeff Winger and Annie Edison. The pairing was simply creepy, especially as Jeff was in his forties and Annie was only 18 in season 1. Although the earlier days of Community pushed the relationship between Jeff and Britta, this eventually fizzled out.

Thankfully, Annie and Jeff didn’t end up together in Community, but their will-they-won’t-they romance was one that ultimately should have never existed in the first place.

Jeff toyed with Annie constantly, and it was ridiculously unfair. After rejecting her, Jeff envied Annie’s romance with Vaughn, even though he didn’t care about her feelings about his other relationships. Moments between the two, like Annie pretending to be Mrs.

Winger, the tension they shared while hunting the “Ass crack bandit,” and the cringey Santa dance, were painful to watch. It logically seemed that nothing would happen with them, but every time it appeared Community had dropped this story, it returned without fail and plagued every season of the show.Thankfully, Annie and Jeff didn’t end up together in Community, but their will-they-won’t-they romance was one that ultimately should have never existed in the first place.

1 Mulder & Scully

The X-Files (1993-2018)

Mulder and Scully in The X-Files were one of the best TV slow burn romances ever, but many felt that the pair took too long to finally get together. While it made sense that they tried to keep things professional, considering their roles as FBI agents, it didn’t make the lack of progression in their relationship any less annoying.

The tension between Mulder and Scully was unmatched, and even though it was clear they were more interested in working with one another than any other romantic interests, they still didn’t sort themselves out. However, in the season 7 episode “Millennium,” they finally shared their first kiss to celebrate the New Year. Their relationship after this was full of difficulties, especially following the birth of William, but the payoff was worth it.

After years of waiting for their love to bloom, and finally getting it, viewers were astounded when The X-Files revival established Scully had split from Mulder. Despite introducing this heartbreaking plotline, they eventually got back together, and Scully announced she was pregnant again in the season 11 finale.

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