The Best and Worst of Phoebe’s Boyfriends on ‘Friends’


So where are you at in your Netflix binge watching of all ten seasons of the sitcom Friends that ran on NBC from 1994 to 2004? I have spoken with many people who have actually finished all 230+ episodes of the series that starred Jennifer Aniston, Lisa Kudrow, Matt LeBlanc, David Schwimmer, Courtney Cox, and Matthew Perry. Over the last few weeks, we here at TVOvermind thought it would be a fun idea to rank all the boyfriends and girlfriends the six main characters dated over the 10-year span of the comedy. Last week, we took a look at all the women from Ross Geller’s life. If you have not checked the article out yet, click here. This week we will take a closer look at the men that were a part of kooky Phoebe Buffay’s life. These men include her husband Mike, her first husband Duncan, and two men that were first a part of her twin sister Ursula’s life.


Phoebe thought it was destiny when she kept running into Jim during an episode of the eighth season of Friends. She quickly broke up with him when she found out that he wrote erotic novels for children and claimed to have a PhD, but not the kind you are thinking.

Boyfriend Grade: F


Phoebe dated Roger during the first season of Friends. The gang did not like him because he would try to analyze their relationships since he was a psychiatrist. Phoebe also began to grow annoyed with him and ended their relationship.

Boyfriend Grade: F


Overall, Parker was a nice guy and he and Phoebe dated very briefly during the eighth season of Friends. She took him to Jack and Judy’s anniversary dinner and realized his fondness for everything and lack of finding anything negative in the world was too much to handle.

Boyfriend Grade: D-


This relationship may have worked if Sergei knew how to speak English. He did have an interpreter, but when he left the date to spend time with Monica, he and Phoebe were unable to communicate with one another.

Boyfriend Grade: D-


Larry was the health inspector that Phoebe dated during season five of Friends. Things were going great until Larry started to shut down all of Phoebe’s favorite restaurants. If she kept dating him, there would be no place left for her and the gang to eat.

Boyfriend Grade: D


Phoebe dated Kyle while Ross dated his ex-wife Whitney. The couple end up getting back together which left Ross and Phoebe angry and alone. At least they had one another.

Boyfriend Grade: D


Tim was Monica’s sous chef that Phoebe was attracted to and started dating during season eight of Friends. Phoebe thinks he is a whiner and wants to ditch him, but Monica wants to fire him from the restaurant because he is not doing a good job. The concept was funny, but that does not make him great boyfriend material.

Boyfriend Grade: D+


Phoebe thought things would work out with Malcolm, even though the two met because he thought he was stalking her twin sister Ursula. Phoebe later breaks up with Malcolm when she decides to follow him and finds out he is still pining over her evil sister.

Boyfriend Grade: C-


Like Malcolm, Eric is a person who was first part of Ursula’s life. Regardless of this, the two try to give a relationship a shot. However, Phoebe decides to end the things when Eric accidentally sleeps with Ursula because he thought she was Phoebe.

Boyfriend Grade: C


Jake liked Phoebe so much that he decided to start wearing her underwear. He was never mentioned again after this episode, so Phoebe must have broke up with him because he ended up stretching them all out.

Boyfriend Grade: C+


Robert was the guy who never wore underwear. No one had the guts to tell him that he was flashing them until Gunther got a look at it during a visit to Central Perk.

Boyfriend Grade: C+


Rob and Phoebe shared a love for music and that is why the two began dating. Rob thought it would be a good idea to have her sing to children, which turned out to be a huge mistake during the second season of Friends. After this, we never heard of Rob again.

Boyfriend Grade: B-


Phoebe was in love with Duncan even thought he claimed to be gay. He visits Phoebe during the second season of Friends. He tells her they need to get a divorce because he has found a woman and wants to marry her. This leaves Phoebe crushed as she has always held a place in her heart for Duncan.

Boyfriend Grade: B


Phoebe begins dating Gary during the fifth season of Friends when she begins to impersonate a cop. Instead of arresting her, Gary takes Phoebe out to dinner. The two eventually move in together, but the morning after the big move Gary shoots a bird and Phoebe is mortified.

Boyfriend Grade: B


Jason was one of the guys that Phoebe was dating at the same time during the third season of Friends. She thought it would be fun to play the field, but then decided she needed to break up with one of them. Jason was the sensitive Kindergarten teacher. When Jason finds out she is dating someone else, he break up with her.

Boyfriend Grade: B+


Vince was the other man that Phoebe was dating. He was a fireman and Phoebe was going to break up with him when she thought he was not sensitive enough for her. When she found out he wrote poetry, she wanted to keep dating him along with Jason. Vince ends things with Phoebe when he learns she is dating Jason too after they bump into one another at Central Perk.

Boyfriend Grade: B+


Ryan was Phoebe’s boyfriend who was in the Navy and whenever he returned to land the two would spend all their time together. On his last visit, even Phoebe’s chicken pox could not keep him away. Sadly, we never heard about him again after this season two episode of Friends.

Boyfriend Grade: A-


Phoebe met David during the first season of Friends. Their relationship would be short-lived as David went to Minsk to do some scientific research. The two would cross paths several times and eventually rekindle a romance during season nine of Friends. However, Phoebe’s heart was with Mike and the two would break up in Barbados so she could be with Mike.

Boyfriend Grade: A-


Mike and Phoebe’s first date was not a typical one. Joey and Phoebe had agreed to set one another up on blind dates and Joey forgot. He found Mike at Central Perk and talked him into meeting Phoebe. The two clicked right away, but would break up during the ninth season of Friends, when Mike admitted that he never wanted to get married again. They would get back together by the tenth season and eventually get married on one of the greatest episodes of the series.

Boyfriend Grade: A

Which of Phoebe’s boyfriends was your favorite? Let us know in the comments section below.

Photo by Frazer Harrison/Getty Images

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