Friends: Ranking Phoebe’s Love Interests

Writer’s block (or in this case, blogger’s block) has been terrible! So, surprise surprise, I’ve been binge-watching my favorite show, Friends again. This time around, I started thinking about all of the relationships we see throughout the show’s ten season run. After thinking about it, I wanted to rank the people the main characters have dated. I wanted to start by ranking Phoebe’s boyfriends because they were the ones that came to mind first. I’m including husbands, boyfriends, dates, hook-ups, and interests. Coincidentally, I completed this article on Lisa Kudrow’s birthday! Happy Birthday, Lisa!

22. Rick


Rick (Jason Brooks) made it to the very bottom of the barrel for me. He was a married man who decided to make out with Phoebe (Lisa Kudrow) and get her fired. Before anyone decides to blame Phoebe on this one, let me explain. If Rick simply told her he was married, she would’ve backed off right away. They wouldn’t have made out, Phoebe’s boss wouldn’t have caught them, and Phoebe would still have her job.

21. Jim


Jim (James Le Gros) was a pure creep. On the very first date with Phoebe, he was completely inappropriate and disrespectful towards her. Even when she expressed how uncomfortable she was with his comments, he just continued. Not to mention he makes erotic novels FOR CHILDREN! That should’ve been the moment Phoebe left. The only reason he’s not ranked last on this list is because even though it was one of the worst dates on the show, it still didn’t cost Phoebe her job and completely turn her life around.

20. Malcolm


I honestly wasn’t expecting to rank Malcom (David Arquette) so low, but reflecting on it, there was nothing in the relationship that wasn’t problematic. For starters, they met by him stalking her! He wasn’t even trying to stalk her, he was trying to stalk her twin sister, Ursula. Then, when she develops a crush on him, she tried to help him get over Ursula. He gave Phoebe his binoculars, a book he pretended to read while watching Ursula, and a notebook where he logged everything she did. When he read about the time he met Phoebe and wanted to kiss her, it was very weird that she found that romantic. If that doesn’t convince you, while he was with Phoebe, he STILL stalked her sister. Also, it seemed the only way for him to get over Ursula was to start stalking Phoebe instead. This guy had a lot of issues.

19. Upstairs Guy


We never saw this guy or learned his name, and the only things we knew about Upstairs Guy (Ira Ungerleider) are that he lived above Rachel and Monica, and that he was a very loud neighbor. This guy was so disruptive and inconsiderate, but he charmed people out of hating him. Once Phoebe started dating him, Monica and Rachel were forced to listen to every bit of their physical encounters. Then, Phoebe was forced to listen to him cheat on her with another woman! It was a straight d**k move and he even charmed his was out of getting his a** kicked by Chandler, Joey, and Ross. Well, he’s not charming his way to a higher rank on this list!

18. Roger


Roger (Fisher Stevens) was a real piece of work. Instead of simply hanging out with Phoebe’s friends, he just analyzed them, made them feel worse about themselves, and believed that was bonding. Then, when Phoebe was truthful about how they felt about him, he decided to insult them, and her, in a very condescending way, which was very childish.

17. Gary


Although I love Michael Rapaport, I was definitely not a fan of Gary. He started out as a sweet cop but he was pretty rude to Phoebe’s friends. Then, whether intentionally or unintentionally, he guilted Phoebe into moving in with him when she simply wasn’t ready. When she lied to him about finding a place, he put her into an interrogation room and treated her like a criminal. I get it’s supposed to be a funny “cop vs. criminal” thing, but watching him talk to her like that was very uncomfortable. Do I even need to mention the bird-shooting incident?

16. Rob


I can’t completely condemn Rob (Chris Isaak) for simply doing his job, but he didn’t really seem to have Phoebe’s back. When he asked her to sing to children at the public library, he didn’t even tell her what kind of songs he wanted her to sing. If he listened to her sing at the coffeehouse, he’d know exactly the kind of quirky, random subjects her songs shine light on. Inappropriate or not, the kids loved the songs she sang and he didn’t even mention that when the library’s board members told him to fire her. She didn’t really hold any ill will though, since they sing together in the end.

15. Duncan


I know they were only married so Duncan (Steve Zahn) could get his green card, but I’m still including him on this list. Phoebe was actually in love with Duncan, but she believed he was gay, so she knew they could never be together. When he couldn’t hide the fact that he was straight anymore, he asked Phoebe for a divorce so he can marry another woman. I can’t really be mad because that woman could’ve been the one who made him realize he was straight, and if he never had feelings for Phoebe, that’s definitely not his fault. Although, if he did admit he was straight before he met the other woman, I think it would’ve given them the chance to maybe pursue each other and who knows? Maybe they could’ve been together all along.

14. Eric


I’m not sure how I’d classify Eric (Sean Penn). On one hand, he was very sweet to Phoebe and an overall nice guy. His biggest problem was he rushed into things WAY too fast. He was going to marry Ursula after knowing her for only two weeks. Then, after ending things with her, he asked Phoebe out on a date a week later. While on their first date, they decided to have sex, or so Eric thought. He rushed into everything so fast, he ended up sleeping with Ursula thinking she was Phoebe! You have to slow things down, dude!

13. Parker


Other than pressuring Phoebe to try an oyster, there wasn’t much else wrong with Parker (Alec Baldwin). Sure, having a constant positive attitude might annoy people after a while. However, Phoebe really liked him and his positivity didn’t even bother her until her friends pointed it out. Even after he and Phoebe fought, he considered it one of the best fights he’s been in. He was definitely more funny than frustrating. Then again, I wasn’t the one dating him.

12. Vince


I never really had a problem with Vince (Matt Battaglia). Although, it was weird that he got really bummed out at the thought of Phoebe breaking up with him because he felt a real connection, BUT when he found out she was dating another guy, he just brushed it off because “they never said they were exclusive.” Plus, breaking up with her because she had a candle-lit dinner in a park seems a little extreme to me. I can definitely understand him getting mad, because he was a fireman. However, ending a relationship with someone you care about over it? Come on.

11. Don


Don (Harry Van Gorkum) is smack dab in the middle for me because I don’t feel love or hate towards him. If anything, I kind of feel bad for him, because even though Phoebe believed he was actually Monica’s soulmate, she still went out with him because “a girl’s gotta eat.” I could be totally wrong here, but it seems to me she was just using him for free food. Before anyone starts talking about him flirting with Monica knowing she’s married, we don’t know for certain that’s what he was doing. Like Monica, Don could’ve viewed it as merely a pleasant conversation.

10. Tim


Tim (Kevin Rahm) was honestly a very nice guy, but he seemed too needy and attached. If he didn’t hear from Phoebe, he’d get very paranoid and obsessive. He’d even go to her house to check on her if he didn’t hear from her soon enough. It’s sweet that he cared, but to care that much in that little time span can be a little overwhelming, bud! I will say this, though: when Phoebe ended things with him, he handled it in a VERY mature way. He was a true gentleman to the very end.

9. Larry


Larry (Gregory Sporleder) was a health inspector that was admittedly too into his work. However, that wasn’t an issue with Phoebe. As a matter of fact, she was drawn to the power. When he considered shutting down her favorite coffee shop though, she finally drew the line. He was very respectful of her wishes and he chose not to shut the place down.

8. Kyle


Kyle (David Sutcliffe) and Phoebe seemed to really get along. Although, with how the episode turned out, it seemed all he ever did was talk about his ex-wife and her issues. That wasn’t the issue with Phoebe though, she was so devoted, she kept fighting with Ross (David Schwimmer), who was dating Kyle’s ex. When Kyle decided to give his marriage another shot, they both broke the news to Phoebe and Ross in a respectable manner. Phoebe on the other hand, didn’t really take the news well.

7. Jason


Jason (Robert Gant) was a pretty cool guy that Phoebe was dating while also dating Vince. He was very mature when Phoebe confessed to dating someone else. To be honest, I don’t blame him for walking out when he found out Phoebe actually slept with Vince. It’s one thing to simply go on a few dinners with someone else, but sleeping with someone else is a whole new level of intimacy and betrayal.

6. Robert


Robert (Markus Flanagan) was a very good influence on Phoebe. He taught her about a bunch of different sports and influenced her to be more active. Everything in their relationship was going great until Phoebe realized he wore shorts that were VERY revealing. The only thing I don’t get is how he couldn’t feel a breeze down there. I think it was very unfair that Phoebe decided to end things just because he didn’t realize he was unintentionally exposing himself. A simple conversation could’ve maybe saved their relationship.

5. Sergei


Sergei (Jim Pirri) was handsome, charming, and he and Phoebe really connected. The only problem was that he couldn’t speak English and they couldn’t understand each other without a translator. After his translator quit, they didn’t give up on each other and that alone was admirable. I know that they eventually broke up, but the fact that he tried his best to be with her when the obstacle in their relationship grew is still commendable!

4. Jake


Jake (Troy Norton) was a really nice and fun guy. He and Phoebe not only got along, they didn’t even want to be away from each other. Plus, he wasn’t afraid to have fun and step out of his comfort zone. When a couple decides to wear each other’s underwear, that’s how you know they’re really into each other.

3. Ryan


Ryan (Charlie Sheen) was very devoted to Phoebe. Even when he’s away at sea for years, he never stopped thinking about her. Unfortunately, when he was spending two whole weeks with her, he found out she has chicken pox! In an incredibly romantic gesture, Ryan willingly gave himself chicken pox so he could be with her. They stuck by each other’s sides and suffered together.

2. David


If David (Hank Azaria) never left for Minsk in season 1, I truly believe they would’ve ended up together and we wouldn’t have this list to begin with. They were crazy about each other, and even after years of never seeing or talking to each other, that connection never left. I believe that he deserved a better send-off at least.


1. Mike


I’m not putting Mike (Paul Rudd) at the top because he’s the one Phoebe ended up with. He’s truly my favorite. He was the normal to her chaos. He kept her grounded while she brought him out of his shell. He chose his love for her over his snobby parents’ wishes. He stood for her, and when she kissed David, he decided to forgive her. He didn’t let the failure of his first marriage keep him and Phoebe apart (for long), and he tried three different times to propose to her. They had their struggles, but in the end, they realized they were meant to be together.

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