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.

In "Friends" Season 3, Phoebe makes a dating mistake with Malcolm. The two meet after Malcolm mistakes Phoebe for Ursula, whom he is stalking. Phoebe confronts him about stalking her, and he explains his love for Ursula is actually clouding his judgment. At first, Phoebe nicely shuts him down, but she finds him charming so she invites him for a cup of coffee. They continue to date for a bit after Phoebe helps him get over his obsession with Ursula. However, he doesn't actually get over this obsession and ends up continuing to stalk Ursula. When Phoebe discovers this, she decides to end things. She does continue to help him get over Ursula, though, by suggesting he stalk her instead.

Need the obvious be stated? Malcolm stalked Phoebe's sister. The show tries to make light of it, but the warped power dynamic in a man following a young woman around New York City is disturbing. Phoebe knew about it and chose to date him anyway. The decision-making on her part is really poor, but the blame should primarily be on Malcolm for his shady behavior. He wasn't even interested in Phoebe but was heavily invested in her sister. That, plus the literal stalking, makes Malcolm the obvious worst choice for Phoebe and could've even put her in some real life-threatening danger.

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.

Phoebe and Robert date in "Friends" Season 3. He's nice and sporty — arguably the only traits we really get to know about him because of his short run on the show. However, when he meets Chandler and Ross, they notice that Robert has a problem keeping his privates private inside his baggy shorts. The entire friend group notices, and eventually, Phoebe does too. She likes him and doesn't want things to end, so she buys him tight pants that are able to stretch. However, he doesn't like them because he doesn't like to wear stretchy pants. Eventually, Phoebe decides to just tell him the truth, but before she can get it out, Robert confesses that women hastily break up with him all the time. He asks if it's something he's "putting out there," and though Phoebe doesn't know what to say, Gunther ends up telling him the truth.

As far as being right for Phoebe, there's nothing so bad about Robert, but if she's thrown off at the first bit of awkwardness, then he's probably not a great match. Fundamentally, they don't have much in common. Sure, he's nice and sporty and gets Phoebe to try new things, but realistically that's not enough to make a relationship work for the long term.

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.

Gary is a cop whom Phoebe meets when she finds his badge and starts impersonating a police officer for fun. This being a crime, Gary could've arrested her when he found out. Instead, he asks her out and the two start up a relationship. Everything goes great at first: The friends like him, Phoebe is happy, and Gary is smitten. However, some tension develops when Gary suggests they move in together. Phoebe is nervous and feels pressured to say yes, and Gary involves Chandler in the situation, which doesn't help. They decide to move in together, but Phoebe ends the relationship when Gary kills an innocent bird chirping loudly outside their window.

Gary and Phoebe have time to develop their relationship over several episodes in Season 5, which is why he ranks higher than most of her flings. However, he isn't really the right match for Phoebe at all. When he chooses to ask Phoebe out instead of getting her in trouble for impersonating a police officer, it might seem like a bit of kind leniency, but it actually makes the whole situation uncomfortable. Essentially, Phoebe is put in a position where if she rejects him, he might arrest her, which is obviously an uneven power dynamic. Though he does show some good qualities while they're together, Gary is very controlling and puts a lot of pressure on Phoebe, ultimately making him the wrong person for her.

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.

Parker is where we start getting into Phoebe's healthier relationships. He and Phoebe meet at the dry cleaners after Phoebe's tea leaves tell her she'll soon meet the man of her dreams. He's immediately smitten with her, and Phoebe is charmed by him as well. They start dating, and Phoebe discovers that Parker is the most positive human being on the planet. When she takes him to Jack and Judy Geller's 35th wedding anniversary party, Parker can't stop pointing out all of the good in the evening and the venue, almost exhaustively so. The friends become annoyed, but Phoebe leans into it. That is, until after the party, when Phoebe can't take it anymore and breaks up with him. Parker's angry about it, but he still somehow remains positive.

There isn't a thing wrong with Parker, other than his ability to magically see the good in every aspect of life. Sure, his positivity can get a bit tiresome, but it's nothing that couldn't have gently been handled by Phoebe. Instead, her patience runs thin, and she snaps at him. It's clear that Parker's positivity isn't right for Phoebe, and that she should be with someone who can move through life with both the good and the bad. However, this isn't Parker's fault. It's just a matter of their personal differences in attitude.

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.

Ryan is a Lieutenant Commander in the Navy and is affectionately called "submarine guy" by Phoebe because he spends most of his time living in a submarine. He typically can only visit Phoebe for three days at a time before having to return to the submarine, until finally he's able to visit for two whole weeks. Phoebe fills up the schedule for them to spend time together, but she accidentally gets chicken pox from Ben and has her plans ruined. However, Ryan misses her so much that he braves chicken pox for her. They spend the full two weeks at home together recovering, trying to make the situation as normal as possible. Even though their romantic two weeks have a wrench thrown into them, Ryan and Phoebe are able to make the best of it together because of how much they care for each other.

On the surface (and because of his profession), Ryan might not seem like the right person for Phoebe, but emotionally he connects with her well. He loves Phoebe so much that he braves chicken pox for her. He not only understands her quirks but embraces them as well. The only problem is that he has to be away from her so often because he's in the Navy, so he isn't exactly the best choice for a long-term relationship. However, he is well suited for Phoebe because they like the same things and are both a little kooky.

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.

Rob works with children and helps to schedule music acts for the local libraries. In an episode of "Friends" Season 2, he approaches Phoebe about performing for a children's library show. She's asked to write some educational songs for the kids and perform them acoustically. When she gets ready to play, Phoebe gets really nervous because she's used to performing for adults who don't really listen, but she knows that kids are more likely to hang on her words. When she's nervous, Rob is able to help her overcome it by kissing her. However, when Phoebe's songs end up being inappropriate for the kids, her children's music career comes to a swift end. Though her relationship with Rob also ends, at least the kids like her music and come all the way to Central Perk to hear more.

Rob seems to be very good for Phoebe, and he helps her overcome her nerves. They're cute together, but their relationship is short-lived, only lasting the length of one episode. If they just would've agreed not to do any more children's shows together, they could've been a great match for each other. Not only that, but Rob is quite charming, and the friends love him too.

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.

Mike Hannigan enters "Friends" and quickly becomes Phoebe's soulmate and true love. They meet because Joey forgets to find a blind date for Phoebe when she's already found one for him, prompting him to turn to a stranger, who ends up being Mike. The date is understandably awkward, but they end up actually hitting it off and beginning a relationship. Everything goes well until Phoebe learns that after his divorce, he vowed never to remarry. Their relationship ends, but they get back together because they love each other so much. Mike changes his mind about marriage when he realizes it's truly what Phoebe wants, and he proposes. They get engaged, get married, and are happy together upon the show's ending.

Mike and Phoebe are without a doubt perfect for each other. He always makes her feel special and happy, and she loves him like she's never loved anyone else. They have the same sense of humor, the same love of music, and they're both very weird in a beautiful way. Mike even leaves his career as an attorney to become a pianist, having demonstrated his talents for Phoebe early on in their relationship. His love for Phoebe is more important than his concerns about marriage, and he ultimately just wants to be with her however he can. Phoebe, unlike a lot of sitcom characters, ends up with the exact right person for her.