Friends has given us some of the most iconic relationships in TV history. From the rollercoaster love affair between Ross and Rachel to the unexpected yet perfect partnership of Monica and Chandler, we’ve all watched, laughed, and cried as these six characters navigated the ups and downs of their personal lives. But… what if things had gone a little differently?
In this article, we’re diving into a fun what if scenario: Who each main Friends character should have ended up with (other than who they did)? While the relationships we saw were satisfying in their own ways, there are a few alternative pairings that might have made even more sense. So, let’s break it down—grab your coffee and get ready to rethink the romantic journeys of your favorite characters.
1. Ross Geller – Should Have Ended Up with… Rachel’s Sister, Jill Green
Let’s face it, Ross and Rachel were always a bit of a hot mess, and the constant drama that defined their on-again, off-again relationship made their eventual reunion feel a little anticlimactic. But imagine a scenario where Ross, instead of reconciling with Rachel, had ended up with Jill Green, Rachel’s younger sister.
Jill, played by Reese Witherspoon, was fun, spontaneous, and had a more relaxed approach to life compared to Rachel. Though she was only around for a brief period, her chemistry with Ross was undeniable. They shared some light-hearted moments, and Jill was much more open to Ross’s quirks than Rachel ever was. Plus, she was far more low-maintenance than Rachel, which might have been exactly what Ross needed. With his insecurities and need for validation, Jill’s easy-going nature would have been a refreshing change.
2. Monica Geller – Should Have Ended Up with… Richard Burke
Monica’s relationship with Chandler Bing is heartwarming and one of the show’s most stable romances. But if we’re going down the “what if” route, there’s a strong case to be made that Monica should have ended up with Richard Burke—her older, suave, and successful boyfriend played by Tom Selleck.
Monica and Richard had serious chemistry, and it was clear that she was genuinely in love with him. Their connection was intense, and they had a deep understanding of each other. Sure, Richard was older, and their differing desires about having children led to their breakup, but imagine if Monica had been able to compromise a bit, or if Richard had been open to having a family. Their relationship was mature, respectful, and full of passion—a stark contrast to Monica’s nervous, fast-paced relationship with Chandler.
While Chandler and Monica’s partnership was built on friendship and mutual respect, Richard would have been an equally compelling match, giving Monica the romantic intensity she truly craved.
3. Chandler Bing – Should Have Ended Up with… Kathy
Chandler and Monica’s relationship was a beautiful, long-term, supportive one, but in an alternate universe, Chandler Bing could have had a much different romantic future—one with Kathy, played by Paget Brewster.
Kathy entered Chandler’s life during a time when he was grappling with his self-worth, and though their relationship was short-lived, it was filled with humor, chemistry, and genuine affection. Kathy was fun, free-spirited, and more aligned with Chandler’s need for someone who could balance out his self-deprecating humor. She also made Chandler feel desired in ways that his previous relationships didn’t quite manage. Had they been given more time to explore their dynamic, it’s easy to imagine a different future for Chandler and Kathy. They were playful, compatible, and emotionally open with each other.
Sure, Chandler and Monica ended up having a family together, but with Kathy, Chandler may have discovered a partner who could bring out his carefree side and help him take risks in life.
4. Rachel Green – Should Have Ended Up with… Joey Tribbiani
Okay, let’s not pretend that Rachel and Joey weren’t amazing together, even though their relationship ultimately didn’t last. Yes, they were an odd pairing at first, but by Season 9, it was clear that Joey Tribbiani truly cared for Rachel in a way no one else had before.
Joey loved Rachel without hesitation, and his kindness, loyalty, and willingness to always put her first made him one of the best partners she could have had. Plus, he was the kind of guy who made Rachel laugh and feel comfortable, something she often struggled to find in her more complex relationships with Ross. While Ross and Rachel’s will-they-won’t-they drama had its charm, Joey was open, honest, and genuinely there for Rachel.
Had they been given more time, it’s possible that Joey and Rachel could have built a lasting relationship. His love for her was real, and he wasn’t afraid to admit it. Plus, Rachel might have had the chance to experience a more laid-back, fun romance compared to the serious, intense one with Ross.
5. Phoebe Buffay – Should Have Ended Up with… David (The Scientist)
Phoebe’s relationship with Mike Hannigan was sweet and ended with a beautiful wedding, but in an alternate universe, Phoebe and David (the scientist), played by Hank Azaria, could have been a fantastic match. David and Phoebe shared a quirky, deep connection from the start, with both of them being offbeat and creative.
While Mike was a great match for Phoebe in terms of stability and love, David had a different energy. He was also deeply passionate about Phoebe’s weirdness, and their chemistry was undeniable. The only issue? David had to leave for a job opportunity, which really left Phoebe torn between her desire for love and her desire to explore new things in life.
If David hadn’t left, or if the timing had been better, Phoebe and David could have been the quirky, intellectual power couple of the show. Their love for each other was pure and deep, and who knows? They might have found a way to make it work long-term.
6. Ross Geller – Should Have Ended Up with… Carol Willick (If She Wasn’t Already Married)
Okay, hear me out: Ross and Carol Willick, his ex-wife, had a really complex and interesting relationship that, under different circumstances, could have turned out differently.
When Ross and Carol first met, there was genuine love between them. They got married, had a child (Ben), and had an honest emotional connection. While Carol’s coming out and their eventual divorce was understandably complicated, they co-parented Ben in a way that showed a level of mutual respect and understanding.
In an alternate universe where Carol didn’t end up with Susan, Ross and Carol could have worked things out and become a more balanced couple. They were both well-meaning and capable of communicating in ways that Ross was never able to with other partners. They could have made a great team raising Ben together. Carol might have been Ross’s true soulmate, if only circumstances had been different.
7. Monica Geller – Should Have Ended Up with… Paul the Wine Guy
Remember Paul the Wine Guy, the guy Monica briefly dated in Season 1? He was funny, charming, and shared an easy chemistry with Monica. While their relationship didn’t last long, there was potential for something more. Paul had a certain laid-back attitude that seemed to balance Monica’s neurotic energy, and they shared a lot of laughs together.
Though he wasn’t the perfect long-term match for Monica, he was certainly a better option than some of her other boyfriends. Had she and Paul continued dating, Monica might have enjoyed a more fun and relaxed romantic experience before diving into her eventual relationship with Chandler.
8. Chandler Bing – Should Have Ended Up with… Kathy (Alternate Timeline)
As we mentioned before, Chandler’s relationship with Kathy was short-lived but had a lot of potential. In an alternate timeline, Chandler could have built a solid life with Kathy instead of Monica. Kathy was independent, fun, and understood Chandler’s sense of humor. She wasn’t bogged down by the serious dynamics of Monica’s life and didn’t feel the pressure of trying to meet her high expectations.
Chandler and Kathy could have been a more spontaneous couple, with less of the emotional baggage Chandler carried into his relationship with Monica.
Conclusion: The Perfect Friends Pairings (Maybe)
As fans of Friends, we’ve all invested in the romances of our favorite characters, but imagining a world where things could have gone differently is fun and thought-provoking. While the couples we saw on-screen ended up being the ones we root for, it’s exciting to think about the possibilities and what other partnerships might have been just as perfect (or even better).
Whether it’s Ross and Jill, Monica and Richard, or Chandler and Kathy
