15 Best Will-They-Won’t-They Comedy TV Relationships

Few television tropes are as timeless as the will-they-won’t-they romance. These relationships thrive on unresolved feelings and the slow buildup of tension, making them some of the most compelling storylines on screen. 

From slow-burns like Pam and Jim from The Office to enemies-to-lovers like Jordan and Marie from Gen V, these relationships keep audiences hooked with their magnetic chemistry. Some couples take seasons to confess their feelings, while others are constantly interrupted by misunderstands or their own fears.

No matter the approach, the best of these storylines balance frustration with emotional payoff, making every moment worth the wait. While audiences find themselves rooting for the couple to finally get together, savoring the anticipation is what makes these relationships so exciting. 

Whether it’s lingering glances or interrupted confessions, the best will-they-won’t-they couples keep viewers guessing and obsessing until the very end. 

In no particular order, here are 15 of the best will-they-won’t-they comedy TV relationships: 

1. Pam and Jim (The Office) 

Few will-they-won’t-they relationships in TV history are as beloved as Pam and Jim’s on The Office. From the very first season, their inside jokes, stolen glances, and playful banter made it clear that they were meant for each other. 

However, for several seasons, bad timing always got in the way. When Pam was engaged to Roy, Jim still had feelings for her so he used pranks and laughter to stay close to her. 

While Jim transferred to the Stamford branch for a season, their separation made the tension even greater. Although Jim initially confessed his feelings to Pam in the Season 2 finale, they didn’t start dating until Season 4. 

Their love story continued to stay strong, and their wedding at Niagra Falls is one of the most iconic wedding moments on television. What made their romance special was the small, everyday moments that showed just how much they loved each other. 

2. Janine and Gregory (Abbott Elementary)

Speaking of workplace romances, one of the best is Janine and Gregory’s relationship on Abbott Elementary. 

Much like how Pam was with Roy before getting with Jim, Janine was dating Tariq when she first met Gregory. However, that didn’t stop Gregory from developing feelings for her, even deciding to stay at Abbott because he found her determination inspirational. 

By the time Janine broke up with Tariq, Gregory had convinced himself to move on. This led to a series of missed opportunities and quiet yearning between them.

At one point, when Janine and Gregory get presents from their significant others, they both find themselves disappointed, highlighting how deeply they understand each other in ways their partners don’t. 

Despite their mutual attraction, they’ve prioritized their work and friendship. But, at the end of Season 3, they finally realize that they can’t deny their feelings for each other and are finally dating.

They try to hide their relationship at first, but all the teachers can tell that they’re dating because of how obvious their chemistry is. As they figure out how to balance love and career, fans can’t wait to see what’s new for Janine and Gregory with every new episode of Abbott Elementary.

3. Eleanor and Chidi (The Good Place) 

If there’s any couple who can prove that soulmates are real, it’s Chidi and Eleanor from The Good Place. They’re the definition of opposites attracting.

While Eleanor lives in the moment and is brutally honest, Chidi overthinks everything and is a chronic planner. From Chidi helping Eleanor become a better person to Eleanor encouraging Chidi to believe in himself, their relationship was more than just romance—it’s about personal growth and second chances.

Despite all odds, such as Michael’s repeated reboots, they finally found their way to each other. In the face of high stakes, they were able to admit their feelings and decide to finally get together. 

What’s most endearing about their relationship is how their love has always found a way to endure. Through every moral dilemma, Chidi and Eleanor have always found their way back to each other, proving some loves are meant to last beyond a single lifetime. 

4. Leslie and Ben (Parks and Recreation) 

Ben and Leslie’s romance is easily one of the best parts of Parks and Recreation. From the moment Ben arrived in Pawnee as a budget-cutting state auditor, his dynamic with Leslie was electric.

Their relationship was built on a foundation of mutual respect, as they recognized each other’s passion and dedication to public service. Even when Ben and Leslie’s feelings for each other became clear, workplace rules and their own ambitions kept them from fully committing to a relationship.

When they finally took the risk and got together, it was all the more satisfying to watch their romance blossom. They support each other’s dreams, with Ben helping run Leslie’s city council campaign and Leslie pushing Ben to run for Congress. 

They never stop uplifting each other, especially when they start a family and face career challenges. Ben and Leslie prove time and time again that they are the ultimate power couple. 

5. Stede and Blackbeard (Our Flag Means Death) 

Historical comedy Our Flag Means Death has been one of the most prominent LGBTQ+ shows. The show’s centerpiece is the romance between Stede and Blackbeard. 

They make an unlikely pairing. Stede is a well-meaning gentleman pirate, while Blackbeard is a legendary pirate known for his fearsome reputation. The show plays into the tension of two very different people slowly drawing closer yet unsure if they can fully trust each other. 

The beauty of their romance is how it’s connected to their personal growth. For Stede, the love story is about breaking free from societal expectations. Meanwhile, for Blackbeard, it’s about letting down the walls he’s built around himself and allowing the world to see him as just Ed. 

Even though the show was canceled only two seasons into its run, Stede and Blackbeard’s relationship will live on to be one of the most iconic queer romances in the world of TV comedies. 

6. Amy and Jonah (Superstore) 

Every moment Amy and Jonah shared on screen together in Superstore was truly like being on Cloud 9.  

Jonah’s idealistic and jokey demeanor contrasts with Amy’s responsible and experienced approach to work. Like many workplace romances, they grapple with navigating personal and professional boundaries. 

Their relationship is grounded in reality, with both characters dealing with difficult matters in their personal lives. A huge plot point involves Amy’s marital struggles and her eventual decision to divorce her husband at the time. 

Ultimately, Amy and Jonah’s romance on Superstore is an honest exploration of the ups and downs of relationships. Their slow-burn relationship kept audiences hooked through all 9 seasons of this iconic sitcom. 

7. Dana and Rachel (Mythic Quest) 

In Mythic Quest‘s fast-paced world of the video game industry, Dana and Rachel took their relationship slowly. 

Their feelings for each other appeared through stolen glances during late-night gaming sessions. However, their own career aspirations do create tensions, especially as Dana earns the opportunity to study programming with Ian while Rachel struggles to carve out her own path. Their differing career trajectories force them to confront difficult questions about ambition and success.

Dana and Rachel’s romance realistically portrays how career pressures can strain budding relationships. One of their most pivotal moments occurs when Rachel questions whether she and Dana are even on the same path anymore. However, their determination to find a way to make their relationship work proves that true love is rooted in mutual support and understanding. 

Through all the professional ups and downs, Dana and Rachel continually choose each other, proving that personal ambition and love don’t have to be mutually exclusive. 

8. Sam and Fred (Crashing) 

In contrast to these slow-burn romances, Sam and Fred’s whirlwind relationship in Crashing is fast-paced and keeps viewers on their toes. 

For the majority of this one-season sitcom, Sam is constantly in denial of his feelings for Fred, even though his jealousy when Fred gets a boyfriend makes his attraction clear. It takes Fred fainting at the hospital for Sam to realize how much he needs Fred in his life.

Sam’s journey tackling his internalized homophobia was necessary for him and Fred together. By the end of the series, Sam and Fred’s relationship is a testament to the transformative power of love and how acceptance is an essential part of romance. 

9. Jess and Nick (New Girl) 

Nick and Jess’s relationship in New Girl is a delightful exploration of the unpredictability of love and friendship. 

The two initially try to resist the attraction due to their contrasting personalities. After all, Nick is a grumpy bartender, and Jess is a quirky and optimistic teacher. 

Yet, their relationship evolves in surprising ways, leading them to find their way to each other. As Nick learns how to open up, Jess also becomes more grounded in her self-confidence.

Their story is about learning to trust and compromise, especially the way love can bloom unexpectedly. Jess and Nick are proof that the best love stories don’t have to follow a straight line but can happen when you least expect it. 

10. Fleabag and the Priest (Fleabag) 

Perhaps one of the most unexpected romances is the one between Fleabag and the Priest in Phoebe Waller-Bridge’s iconic dramedy Fleabag. 

Their connection is filled with undeniable chemistry and emotional intensity, but it’s also defined by their conflicting desires and circumstances. The Priest’s vow of celibacy and Fleabag’s emotional baggage make for daunting barriers that keep them from outwardly expressing their desire for each other. 

Religion and philosophy play important roles in their fledging relationship. When the Priest asks Fleabag if she believes in God, she responds, “I want someone to tell me what to believe in.” This reflects Fleabag’s longing for love and her endless search for meaning and purpose. 

Unlike most other will-they-won’t-they romances, Fleabag and the Priest don’t end up together. After they sleep together, the Priest decides he will choose faith over their relationship. Their last exchange is one of the most iconic heartbreaking conversations: “I love you.” “It’ll pass.” 

It’s a moment that captures the show’s exploration of love and loss as Fleabag walks away and the series ends. Their time together helped Fleabag confront her emotions and find closure. 

11. Jessie and Tom (Starstruck) 

The romance between Tom and Jessie in Starstruck proves that fame isn’t all it’s made out to be. 

Their relationship shows how challenging it can be to maintain a relationship when public expectations put pressure on it. Despite the glamor of Tom’s world, the couple constantly faces moments of uncertainty and miscommunication, leading to a constant on-and-off relationship. From the beginning, Jessie struggles to adjust to dating a movie star, feeling out of place in Tom’s world. 

Whether dealing with the paparazzi or attending events where she feels like an outsider, she constantly questions if she belongs in his life. Meanwhile, despite his success, Tom wants a normal relationship and feels that Jessie is pulling away. Their constant miscommunication, like when Jessie decides last minute not to move in with Tom, tells of how roller-coaster-like their relationship is. 

Much like Fleabag and the Priest, Jessie and Tom decided not to get back together. They finally accept that no matter how hard they want their relationship to work, their lives are incompatible. It’s sad, but it also illustrates the importance of putting one’s needs first. 

12. Issa and Lawrence (Insecure) 

The romance between Issa and Lawrence in Insecure is a compelling journey of growth and self-care.

At first, their relationship is a conventional image of young love, but they quickly face several challenges related to their own personal problems. Their time apart serves as an essential part of their development that helps them understand what they want from life and love.

When they get back together, their romance is stronger than ever, marked by their reconciliation of the past and a desire for a fresh start. Their story is an inspiring tale about the value of maturity and recognizing self-worth in every relationship. 

13. Elena and Syd (One Day at a Time) 

Elena and Syd’s relationship in One Day at a Time is a perfect example of young love. 

Their chemistry is undeniable from the moment they meet, but they take time to navigate their individual identities. Their relationship isn’t just about romantic love but also about discovering who they are and how to support each other in a world that feels uncertain. This is especially true since Syd identifies as genderqueer, and their relationship is the first queer romance on One Day at a Time. 

One of the most touching moments of their relationship comes when Elena is nervous about attending her father’s wedding after he initially struggles to accept her sexuality. Syd offers reassurances and helps Elena prepare for a confrontation. Their unwavering support in that moment highlights how thy uplift each other in their growth journeys. 

Elena and Syd’s journey is a refreshing and inspiring portrayal of young queer love. They’re proof that even in the face of societal challenges, love can be a transformative, validating experience. 

14. Jake and Amy (Brooklyn 99) 

Amy and Jake in Brooklyn 99 are a total couple of goals, even if they first started off on rocky terms. 

It’s no surprise that Amy and Jake butted heads initially since Amy is all work and no play, whereas Jake seems to treat his work like a game. But after a couple of cases, Jake starts bringing out Amy’s silly side and Amy brings out the genuine parts of Jake’s personality. 

Plenty of obstacles (including funerals) prevent Jake and Amy from getting together. But once they start officially going steady, they still find ways to keep their relationship fun.

This comes out especially strong through their yearly heists. Their romance reminds us that joy and laughter are essential for keeping a relationship fresh. 

15. Jordan and Marie (Gen V) 

A great example of true enemies to lovers is Jordan and Marie from Gen V. 

At first, they treat each other like competition, especially Jordan, who wants to stay at the top of the class leaderboard. But eventually, they begin to recognize that they’re more similar than they thought.

Both Jordan and Marie struggle with their abilities and their self-worth. As their connection deepens, they confront their own fears and the pressure the world places on them together.

Their romance is marked by their resilience and decision to stay together despite all odds. Not even the sinister inner workings of Godolkin University can stop these lovebirds from finding their way to be together. 

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That concludes our list! Which of these romances is your favorite? Are there any will-they-won’t-they relationships we didn’t mention in this list? Let us know in the comments below!

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