Friends’ Richard - The One that Got Away

What if Friends’ Richard Burke (Tom Selleck) is “the one” for Monica? He’s a handsome, successful doctor and the two of them shared a mature and genuine relationship. So why did Monica let him get away? Watch this video to explore why this couple didn’t get together by the end of Friends and what The One That Got Away tells us about romance.


What if “the one” isn’t the one you’re supposed to be with? Friends poses this question through Monica’s romance with Richard Burke, the dapper ophthalmologist who also happens to be her parents’ best friend. In the context of the era when Friends aired, Richard appears as the perfect guy, equally admired in the eyes of women and men. After a series of unexceptional men who haven’t made a lasting impression on Monica, Richard opens up her world to a completely new level of love and passion. Yet he’s a temporary visitor. Richard is “the one that got away” — that most exalted ex who changes your life forever and holds a special station in your heart, but who’s not right for you in the long run. This character represents the path that may seem better than what we actually get, but that ultimately isn’t preferable to real life. Here’s our take on Richard and the enduring power of the one-that-got-away trope onscreen.

The Perfect Guy

Part of why Richard looms so large is that he’s made out to be the ideal man. First of all, he’s played by ‘80s icon Tom Selleck, who became a sex symbol as the star of crime drama series Magnum PI, and who established his lovable-cool reputation in popular movies like Three Men and A Baby. So when Friends aired, the character of Richard channeled Selleck’s real-life charisma, and this is cemented within the show by almost everyone in the Friends’ fictional world is in awe of Richard. And to top it off, the writing underlines that — far from being superficial or full of himself — this successful doctor is also a deeply kind person.

Monica Geller: “What were you doing in Africa?”

Richard Burke: “Working with blind kids.”

Monica Geller: “Ugh, what are you doing to me?!” - Friends 6x25

Moreover, Richard’s relationship with Monica possesses all the ingredients of a great romance. They have a backstory, but they meet again after many years when one is unrecognizably transformed. And only one episode after their meeting, their smitten feelings are already blooming into love. The lovers face significant obstacles — chiefly, the stigma of their May-December romance, and the disapproval of Monica’s parents — which push them to loudly proclaim their commitment to each other. The revelation that Monica is only the second woman Richard has slept with…

Richard Burke: “I’ve only slept with women I’ve been in love with.” - Friends 2x18

… also confirms that this relationship is unique and special, not the clichéd cheap dalliance the world assumes it to be. This cigar-smoking, old-school gentleman is clearly a major step up from the childish, unremarkable guys Monica has dated up to this point — making her realize she deserves to be with a true catch who’s crazy about her.

On a deeper level, Monica’s romantic fixation on a man so closely associated with her parents may also have an underlying psychological significance. It’s a running joke that her parents are hyper-critical of her and openly favor her brother Ross. So hooking up with Richard could be a way of seeking the validation and love she’s lacked from someone who is essentially a stand-in for them. But when she defends her relationship in spite of her parent’s disapproval…

Monica Geller: “This is the best relationship I’ve been in—”

Judy Geller: “Oh, please! A relationship?”

Monica Geller: “Yes, a relationship!” - Friends 2x16

… Monica uncharacteristically defies the mother and father she’s usually falling all over herself to please, and this act of courage represents a key moment of maturity.

Besides being Monica’s dream guy, Richard is also the man other men want to be. Chandler’s initial worship of this man when Monica and Richard are together explains why, after coupling up with Monica himself years later, he’s extremely threatened by the memory of her ex. While Chandler’s manhood is frequently the subject of scornful jokes, Richard is a paragon of masculinity. And while Chandler can be painfully self-conscious and awkward, Richard is the picture of confidence and charm.

Richard Burke: “As a poet once said, ‘In the sweetness of friendship, let there be laughter and sharing of pleasures… for in the dew of little things, the heart finds its morning and is refreshed.”

Chandler Bing: “What?” - Friends 6x24

All in all, Richard seems to embody an objectively “better” life path that Monica arguably should have taken. This is an idea that’s been explored in other stories that set up the heroine to choose between a polished, perfect guy and his seemingly less impressive counterpart. But it should tip us off that the heroines of these stories tend to choose the guy who the world sees as less worthy — because what looks right on paper doesn’t always make sense for you.

The Importance of Timing

Monica and Richard embody an all too relatable relationship pitfall: it’s possible for no one to do anything wrong, and for a couple’s love to remain as strong as ever, but for their chance at happiness to be tragically wrecked by timing or conflicting dreams.

The true source of this couple’s incompatibility is their age difference — so you could say their timing is off by quite a number of years. When they start dating, Monica is in her twenties and just starting to figure out her life, while Richard is a settled grandfather. The milestones Monica looks forward to down the road are already in his rearview mirror. Even though Richard may initially seem to fit seamlessly into the friend group, he’ll never quite feel like a peer to Monica and her intimate circle.

More importantly, though, Monica and Richard discover they have very different visions of the future. The couple’s strong love for each other comes through in the way each tries to put their own wishes aside — but in the end, this kind of extreme compromise isn’t fair to either of them.

In season six, when Monica has since moved on with Chandler, Richard reappears and suddenly is willing to offer her everything she wanted.

Richard Burke: “I want to spend my life with you. I want to marry you… I want to have kids with you.” - Friends 6x25

The irony is that at this point Monica and Chandler almost break up for the same reason she and Richard split: thanks to Chandler’s elaborate ruse to mask his intention to propose, Monica believes she and her partner want different things. So during this moment of disconnect, Monica is briefly drawn back to the man who expresses that he is ready for a mature, serious commitment. All this underscores the supreme importance of timing. Like the best One-Who-Got-Away stories, Richard’s regrets warn us that you might not get another shot with the love of your life, so you have to take your opportunity when it comes.

On closer inspection, the episode of Monica turning down post-change-of-heart Richard also illustrates how much Monica’s perspective has been shaped by her initial break-up with him. In season eight, when Phoebe believes she’s found Monica’s soulmate, Chandler is alarmed to see that Monica and Don’s preferences and interests do seem almost ideally in sync. But unlike Rachel, Monica isn’t swept up in the romance of finding your soulmate. And this grounded, realistic outlook on love no doubt has been partially formed by the fact that she already didn’t end up with the perfect guy. Monica chooses Chandler over Richard because they have built something rich and real together. And ultimately, in Monica’s view, a successful partnership is defined by the choice to commit and do whatever it takes to make it work.

The Ones That Got Away

The Monica-Richard relationship falls into a larger canon of “one that got away” stories onscreen. Yet the key takeaways of this narrative can differ drastically. If we look closer, we can distinguish three main categories…

First, The Stepping Stone: Through this lens, the one that got away is a formative rite of passage that makes you evolve and grow as a person, and often leads you to a new, better love. Monica herself embodies this outlook. Yes, she’s completely gutted after her breakup with Richard — she can’t resist giving their relationship another try and later even briefly dates Richard’s son Timothy, which is really just a subconscious way of trying to feel close to her ex again. But in due time, Monica fully moves on. Nonetheless, having experienced this defining love helps her understand what she needs from a forever partnership. Her healthy loving relationship with Richard gave her a strong sense of self-worth, which makes her equipped to “teach” Chandler how to be in a secure, adult partnership.

Second, The Tragic Loss: This take on the one that got away frames it as a haunting missed opportunity to be bitterly regretted and perhaps never fully recovered from. In Mad Men’s final season, the show implies that Don Draper has spent years repressing his longing for his lost love Rachel Menken. It’s notable that, while the relationship with Richard is category 1 for Monica, in Richard’s point of view, their love affair falls into category two. When she mentions having lunch with him in season five, it’s clear that she’s completely over him, but we discover later that this casual encounter left him reeling. She is that looming ghost who haunts his memories. And this illustrates the unsettling truth that, within a single relationship, it’s possible (and common) for two people to have wildly different takes on the lingering significance of their bond.

Annabelle Mathis: “You were the one.”

Roger Sterling: “You weren’t.” - Mad Men 3x11

Finally, there’s type three, The Fantasy Fulfilled: These stories offer the irresistible wish fulfillment of getting a second chance with the one that got away. Before Sunset shows Jesse and Celine reuniting nine years after their first encounter and saving each other from continuing along their unsatisfying life paths — a point underlined by the Nina Simone song that plays in the final scene, “Just in Time.” In Avengers: Endgame, Marvel’s Captain America also gets a happy ending with his love Peggy after initially being cheated out of it. And Friends’ own Ross and Rachel manifest this dream for the viewer too.

Rachel Green: “I got off the plane!” - Friends 10x18

A subversion of category three is the story where a character reunites with an old love interest and is totally disillusioned, realizing that what seemed so romantic in their head falls flat in reality. This reveals that often, the allure of this figure who’s always out of our grasp isn’t really about them at all — it’s about us trying to prove something to ourselves, or to recapture who we were when we knew them. The Age of Innocence initially frames the doomed affair between Newland Archer and Countess Olenska as a category two, the tragic missed opportunity — but Newland goes on to build a genuinely happy family life. And in his later life, after his wife dies and he has a chance to reunite with the Countess, he’s too attached to the long-cherished idea of his lost love to see it replaced by cold hard reality — which underlines that so often we’re really hooked on some mental conception of the one-who-got away, not the flesh-and-blood person.

So ultimately, “the fantasy fulfilled” category is usually just that — a fantasy to be enjoyed onscreen but rarely experienced.

The last we hear of Richard, he’s doing just fine. The show even hints that he’s no longer so hung up on Monica, as he’s erased their sex tape to record himself with another woman. As almost all of us know from mourning our own ones-who-got-away, life eventually must go on. While we might occasionally entertain the bittersweet dream of what could have been, most of us do come to find a sense of peace with our real lives. Take The Umbrellas of Cherbourg: when Guy and Geneviève reunite years after their split, the past that could have been remains painful to them both, but Guy isn’t interested in reopening old wounds, and the movie ends with him joyfully playing in the snow with his wife and son. Friends’ own Phoebe also gets a second chance with her one who got away, David, but by this point, she’s really into someone else.

Meanwhile, stories that go in the opposite direction and do reunite a former couple can sometimes ring false. The entire premise of How I Met Your Mother is based on category 1 — the idea that the many women Ted dates are all stepping stones on the way to the most important woman in his life: the titular mother, Tracy. But in a last-minute twist, the series finale revealed that Ted was actually going to end up with his one-that-got-away, Robin, and this was now a category 3 “fantasy fulfilled” story (or even a category 1 story where Tracy was the stepping stone, not Robin).

Penny Mosby: “You made us sit down and listen to this story about how you met Mom. Yet Mom’s hardly in the story. This is a story about how you’re totally in love with Aunt Robin.” - How I Met Your Mother 9x24

And the disappointed audience reaction underlined that finding your way back to an old flame after many years can make more sense in theory than in practice.

As Cheryl Strayed writes in her “Dear Sugar” advice column, “I’ll never know and neither will you of the life you don’t choose. We’ll only know that whatever that sister life was, it was important and beautiful and not ours. It was the ghost ship that didn’t carry us. There’s nothing to do but salute it from the shore.”

Still, while Monica may have overcome all romantic feelings for Richard, his influence on her can’t be erased. The important people who cross through our lives imprint a part of themselves on us. Most “one that got away” relationships are truly gone for good. But if we listen closely, we can still hear the echoes of that love reverberating through us.

Ilsa Lund: “When I said I would never leave you—”

Rick Blaine: “And you never will.” - Casablanca

Works Cited

Strayed, Cheryl. “DEAR SUGAR, The Rumpus Advice Column #71: The Ghost Ship That Didn’t Carry Us.” The Rumpus, 21 Apr. 2011.