It’s hard to name a more lovable eccentric on TV than Phoebe Buffet. When Friends premiered in 1994, the audience instantly fell in love with the singer-songwriter-masseuse for her odd wit and unconventional nature. That being said, at the heart of the character is a true humanitarian. From her complicated past to her ongoing activism, she always gives the audience someone to root for.
Having grown up in an unstable environment, her search for the love and security that she missed out on as a child makes her love slightly complex. From creepy stalkers to sweet scientists, her dating history has some highs and a few lows. Luckily, her journey to get there has more laughs than tears, and it’s all thanks to her quirky optimism and perseverance that fans adore.
Least Likable: Malcolm
One of the most heartbreaking things about Phoebe is her torrid relationship with her twin sister, Ursula. When Phoebe notices she is being followed by a man, Malcolm (played by David Arquette), she confronts him only to learn that he thought he was following her sister this entire time.
Phoebe takes a liking to him despite all the red flags, including the fact that he is carrying around night vision goggles and a notebook detailing "Ursula's" every move. Malcolm's behavior is creepy and he's untrustworthy and only dates Phoebe because she reminds him of her sister.
Roger
Roger starts off as a potentially good match for Phoebe. He’s an intelligent and insightful psychologist who appears to fit in well with the gang until his analytical eye causes a major riff.
His psychotherapy of her friends leaves them all feeling cold towards him, which leads to Phoebe having to choose between them and him. She chooses her friends and breaks it off with him, but not before he goes on a rage-fuelled tangent mocking the gang's co-dependency.
Parker
When Phoebe brings Parker (portrayed by Alec Baldwin) to Ross and Monica’s parent’s anniversary party, it appears that she might have met a good match. She sees his optimism and zest for literally everything as a sign of someone who is fully alive and appreciative of even the smallest of things. The only issue is that everyone but her finds him extremely annoying.
After some time, Phoebe’s rose-colored glasses come off, and she becomes exhausted by his peppiness, which results in her bidding him adieu.
Duncan
Even the most seasoned Friend’s fan might forget that before she was married to Mike Hannigan, Phoebe was married to Duncan, a Canadian figure skater who needed a Green Card. She plays off the marriage as a simple favor, much to Monica’s dismay, who reminds her that she was once so heartbroken over him that Phoebe, a diehard vegetarian, ate a cheeseburger. When the Ice Capades tour comes to town, he uses their reunion as an opportunity to request a divorce, so he can marry someone else.
He uses Phoebe to obtain his American citizenship, and while she knowingly consents to the marriage, it’s hard to shake the impression that he took advantage of her sweet nature.
Eric
Over a two-episode arc in season 8, Phoebe and her sister, Ursula, encounter another love triangle. Academy Award winner Sean Penn guest stars as Eric, a second-grade teacher and Ursula’s fiancé. Phoebe develops a crush on him and discovers that Ursula has been lying about her through the entire engagement. He breaks things off and decides to start a relationship with Phoebe instead.
Eric is undoubtedly endearing due to his nervous and soft-spoken nature. Still, when he accidentally mistakes Ursula for Phoebe, it becomes clear that their coupling is too weird and unrealistic to pursue.
Ryan
When naval officer Ryan (guest star Charlie Sheen) arrives in New York for a visit, all her romantic plans come to a halt after she contracts chickenpox. She ends up passing the virus on to Ryan and the two spend his visit attempting to enjoy each other's company while trying to manage their symptoms. Watching them avoiding scratching makes for great physical comedy but distracts viewers from really seeing who Ryan is.
He’s a nice guy on the surface, even though the two are irresponsible for spreading the pox. In the end, he is not a viable long-term option for Phoebe, as his military career keeps him away for months to years at a time, but there’s no denying that he cares for her.
Sergei
Phoebe always finds her love interests in the most interesting of places. After offering massage at the UN, she meets a foreign diplomat named Sergei. Although neither one of them speak the same language, they manage to go on a couple of dates, and according to his translator, Mischa, he’s saying all the right things.
Despite a heated argument with Mischa, Sergei is, as Phoebe describes, “dashing” and “sophisticated.” He’s cultured, intellectual and treats her with respect. Between her knack for picking up languages like French and his access to interpreters, it’s a safe bet that these two probably could have pursued a relationship. Still, with Mischa always looming presence, a lack of privacy stalls any progress.
Gary
In many ways, Gary was a good match for Phoebe. He cares about her, protects her and has an adventurous nature to him that she enjoys. In fact, she and the NYPD detective become so serious that they eventually discuss the prospect of moving in together, despite Phoebe’s hesitation.
Luckily, Phoebe ends things before they take the big step after he shoots a noisy bird. If there’s one thing Phoebe won’t compromise on, it’s her ethics, and while it’s sad they didn’t work out, it’s nice to know that she puts her morals first.
David
When David first appears in season 1 of Friends, it almost seems as if Phoebe has found her soulmate. They are head over heels for each other and David’s respect and care for her is admirable. However, when a work opportunity arises, the scientist has to choose between her and his career.
Ultimately, with Phoebe’s blessing, he moves to Russia to pursue his career but makes a couple of cameos throughout the series. It’s hard to point out many flaws when it comes to David, who will always leave fans asking, “What if?”
Most Likable: Mike
Over Friend's run, Phoebe went through surrogacy, grief, a divorce and a slew of family revelations. So, when she meets Mike Hannigan (played by Paul Rudd) in season 9, it's nice to see that she's finally found a source of support and care that exists outside her friends. One of the best things about Mike is that he loves her unconditionally. He even stands up for her when his snooty parents are put off by her earnest and eccentric personality.
Coming off a painful divorce, the former lawyer-turned-pianist has his share of commitment issues but eventually overcomes them. In the final 10th season, the two marry in a winter wedding that leaves fans reaching for the tissues and knowing that Phoebe's story ends on a happy note.