Every Boyfriend Of Friends' Phoebe Buffay Ranked

When fans hear the familiar tune of "Smelly Cat" against a backdrop of the small stage and lone microphone at Central Perk, Phoebe Buffay is sure to be captivating audiences with her original acoustic guitar set. Throughout the entire run of "Friends," Phoebe's music is one of her main priorities. She plays open mic nights at Central Perk, garners music video deals, and even uses her songs to pay homage to her friends, all because playing music and writing her own songs is what she loves to do.

Though music is a huge plot line for Phoebe's character, another thing that fans love about her is her big heart. She's always understanding with her friends' struggles and prioritizes Monica, Rachel, Chandler, Joey, and Ross like they're her family, being that they're the only family she's ever really known. Even with her twin sister Ursula, who shows her nothing but disrespect at every turn, Phoebe chooses to be kind because that's who she is fundamentally.

Because of how much Phoebe cares for humanity and opens her heart to people, she ends up in a lot of different romantic relationships. Across 10 seasons of "Friends," Phoebe tells her friends (and, by extension, the audience) some beautiful stories and some horror stories about her dates, flings, and serious suitors. Based on her personality and the way the men treat her, here are some of Phoebe's most serious flings and relationships ranked from worst to best.

Roger doesn't stalk Phoebe or her sister, but he's still a terrible match for her. One of Phoebe's flings in "Friends" Season 1, Roger initially fits in with the group and provides insight into their problems using his psychiatric license. At first, he really likes them and finds himself interested in their quirks. However, the more he plays psychiatrist instead of acting like a normal significant other of one of the group members, the more the friends start to hate him. They find his "help" to be offensive, especially because he can read them so well and knows things about their lives that they haven't told him. Phoebe becomes frustrated that Roger and her friends aren't clicking, so she talks to him about it. In response, he goes on a tirade about how awful her friends are and how the group dynamic is toxic. Phoebe realizes Roger's nasty true self and breaks up with him.

Psychiatrist or not, it's rude to try and mentally diagnose people you hardly know for no reason other than to exhibit power and superiority over them. If the friends wanted to see a therapist or work on their issues, then that's their prerogative. Roger uses his license in an invasive and rude way, and there are few bigger red flags than someone you date who your friends don't like.

Sergei walks onto the set of "Friends" from a country that Phoebe can never seem to remember the name of — a diplomat who works with a translator, Mischa, to get around in America. Phoebe falls for him pretty quickly, but she becomes frustrated with the language barrier and Mischa's habit of interrupting naturally romantic moments. To combat this, Phoebe invites Monica to go to dinner with the three of them so that Mischa can have someone to talk to while she and Sergei get alone time together. Mischa and Monica get along well, but Phoebe's plan backfires because the translator is so invested in Monica that he doesn't spend any effort actually translating.

Obviously, Sergei and Phoebe weren't going to work because of the intense language barrier and the lack of effort from either party to learn the other's language. However, Sergei is better than a bunch of the men that Phoebe dates. He has a good career, and he's always kind and well-intentioned. Sergei even makes the effort to bond with Phoebe over music when language fails him because he knows how passionate she is about the guitar. Phoebe sings "American Pie" with him in his language, and though she becomes slightly frustrated, she still recognizes that he's making an effort. The fact is, they couldn't speak the same language, so the relationship wasn't going to be able to work. Aside from that, though, they seem to get along fine.

Eric and Phoebe meet at Monica's Halloween party, where Eric shows up with Phoebe's sister, Ursula. The two are engaged, but upon talking to Eric more, Phoebe realizes that Ursula has lied about pretty much everything and painted herself in a completely different light for Eric. Phoebe really likes Eric, and when Ursula leaves her bag at the party and Eric comes back to get it, Phoebe decides to do him the courtesy of telling him the truth. Later, Eric tells Phoebe he broke up with Ursula and wants to see her instead. Though they like each other, Eric has trouble seeing Phoebe without thinking of Ursula. The two of them work it out, but Ursula later imitates Phoebe to have sex with Eric. This causes an irreparable rift between the two, and they end things.

First off, dating your sister's ex isn't a good look. Phoebe and Ursula have massively different tastes, and for Eric to so quickly become involved with his ex's twin isn't a great look for him either. He falls hard for Ursula and is really hurt by her actions, so there's no scenario in which it would be healthy to start a relationship with someone with the same face. Though Eric is a good person who hits it off with Phoebe immediately, there's no real chance the couple would have worked just because of how weird it all is.

Phoebe starts dating both Jason and Vince in "Friends" Season 3. Jason is a kindergarten teacher, very kind, and very in touch with his sensitive side. Vince is a firefighter. Phoebe starts dating them both at the same time and finds herself unable to decide who to ultimately choose, as she struggles with "playing the field." She likes Jason and the fact that he's emotionally in touch, but she doesn't like that he doesn't seem that "manly." It's the reverse for Vince: She likes his manly side but wishes he were more emotional. She goes to break up with Vince, only to discover that he's pretty sensitive after all, so she decides to break up with Jason instead. However, she discovers that Jason has a really hot body and is good with his hands, so she keeps dating them both. They discover one another, and at first, they're kind about it, but they both ultimately decide to break up with her.

Jason and Vince are essentially the same, just presented initially as the reverse of one another. They both seem equally good for Phoebe, and there's nothing really wrong with either of the men. The whole love triangle situation just ends up being too much for them both.

Jake and Phoebe date briefly for two episodes of "Friends" Season 7. At first, Phoebe tricks Monica into thinking that Jake is trying to get Monica's attention. When Monica tells him she's engaged, Jake tells her that he was actually trying to get Phoebe's attention, and the two start up a fling. Joey and Jake start hanging out and go to a New York Knicks game together. When Jake bends over, Joey sees that Jake is wearing women's underwear and is immediately confused by this fact. He talks to Phoebe about it, and she tells him that it was Phoebe's idea to switch underwear and that she's also wearing Jake's briefs. Joey tries to tell Phoebe that he doesn't think Jake is masculine, but Phoebe believes his openness shows a deep comfort in his own masculinity. Though everything seems to be great between the two, Jake is mysteriously never seen again after this episode, nor is he ever brought up.

Jake is a great match for Phoebe. He's really fun, he gets along with her friends, he's comfortable in his own masculinity, and he has a lot in common with Phoebe. He's also clearly open to trying new things sexually, which is great for Phoebe. The audience deserves to know why Jake was written off the show and didn't get to stick it out.

David is a scientist who meets Phoebe at Central Perk during one of her acoustic sets. He tells his friend that he thinks she's the most beautiful woman ever, and though Phoebe gets mad at him for talking during her set, she forgives him upon hearing this. The two strike up a relationship, but David is forced to choose between staying in New York to be with Phoebe or taking advantage of a big work opportunity to study in Minsk, Belarus. He halfheartedly decides to go, and Phoebe is heartbroken. David does come back in Season 7, and they spend one night together. He comes back in an even bigger way in Season 9 and tries to propose to Phoebe. However, she's still in love with Mike and accepts his marriage proposal instead, and David leaves Phoebe alone.

David is a great match for Phoebe. He's smart, pursues the career he loves, and treats her like a queen. He never makes her feel stupid, and when he talks about his scientific work, he makes sure to explain things that she doesn't understand. It's clear that he always wanted what was best for Phoebe, which is why he's so respectful when she turns him down for Mike. David really loves her, and it shows through his affection and his actions.