Phoebe Buffay will probably go down in history as one of the best characters on television. Everything from her dialogues to her iconic musical performances come together to form the special snowflake that is Phoebe. While Friends simply wouldn’t be the same without any of the core six, Phoebe’s absence would probably be the one most people would miss. Her energy was always contagious, and everyone can agree that she got the happy ending she deserved.
However, it was quite a rocky and entertaining road to get there. Just like Monica, Chandler, Rachel, Ross, and Joey, Phoebe’s journey in the dating world was interesting at best, and ridiculous at worst. Many were the men who crossed Phoebe’s life and heart, but which ones are the worst, and which ones deserve some praise? It’s time to rank Phoebe’s boyfriends.
Robert
Arguably one of the funniest characters on the show, it seems only fitting that Phoebe had the funniest boyfriends. The entertaining element has less to do with the things that came out of their mouths, and more with certain characteristics and preferences they displayed.
Let’s take Robert, for example. The first entry on our list, Robert still wasn’t the least memorable out of all the men Phoebe had a fling with. What made him so remarkable were his underwear choices. As in none. Robert was a fan of letting it all hang out just like God intended before boxers were invented. He was great at sports, but no one needs to see that, mate.
Sergei
You know what, Sergei had it all. He was a powerful diplomat, handsome from head to toe, and the human embodiment of the word gentleman. Too bad he didn’t know a single word of English, thus making any sort of verbal communication with Phoebe completely impossible. And a relationship based on physical chemistry alone couldn’t take them anywhere
It did make for some unbelievably funny moments when Monica came along on their date and spent the entire night talking to the translator. We kind of wish we had the chance to get a little bit more from Sergei because he looked like an awesome guy. But maybe a little too uptight for Pheebs?
Roger
Let Roger serve as a lesson for everyone out there reading this list - do not, we repeat, do not, date a psychiatrist who has absolutely no problem deeply analyzing your friends outside of the office. That is bad news because guess what, people resent being analyzed without asking.
Everyone in the group hated Roger, and when Phoebe made sure he was aware of the fact, he revealed how much he despised them as well, and had an actual breakdown himself. He was thoroughly entertaining though, and so was the hairdo.
Eric
Even if he wasn’t portrayed by Sean Penn, Eric still would have made his way to this list. But the fact that he was, definitely grants him some extra points. Phoebe meets Eric when he’s engaged to her evil twin sister Ursula. She breaks them off by revealing all of the lies told by Ursula, paving the way for a blossoming romance between Eric and herself.
The catch? Eric can’t stand her face. Can you imagine dating someone who hates your face? And then he went ahead and slept with Ursula thinking she was Phoebe. The whole thing was so messed up and yet so entertaining there’s no chance anyone will ever forget Eric. Also, because he was Sean Penn.
Rob Donan
We’re still a little salty over Phoebe and Rob’s break up. Rob was absolutely perfect for Phoebe because he was also a musician, and he was played by the music industry hunk Chris Isaak. What’s not to like? They could have had something great together, and the end of their relationship is definitely Phoebe’s fault.
He asked her to play for some children, and Phoebe couldn’t help but bring up some seriously mature themes. The parents weren’t happy, and Pheebs didn’t take it lightly when Rob broke the news. This is another one for the Buffay history books on terrible moves in the family.
Ryan
Charlie Sheen can brag about playing one of his most likable characters on Friends. He was Ryan, the handsome navy officer who met up with Phoebe every time he came to shore. Needless to say, the two of them enjoyed many passionate nights together. And they were hoping for another one by the time we finally meet him.
Unfortunately, both of them contracted chickenpox, and the sexy times had to take a backseat. It was still a very sweet and entertaining episode overall, and Ryan still remains in our memories as one of the best out of Phoebe’s flings. We can’t help but wonder what life would’ve been like if he didn’t have to return…
Gary
Gary seemed great. Plus, how many people can brag about the fact that they met their police boyfriend after finding their badge on the street and using it? Which is, by the way, very much against the law. But Gary was taken enough with Phoebe to overlook this, and the two began what seemed to be a cute relationship.
But this is Friends, so no, they didn’t end up together. Once the pair decides they are smitten enough with each other to move in together, Gary uses his gun to shoot a chirping bird on their window. What the heck, Gary? You were supposed to be one of the good guys! We still appreciate his run on the show, though.
Vince
Vince came along at a time when Phoebe was torn. Dating both him and kindergarten teacher Jason at the same time, our girl didn’t know which one she should choose. She was actually about to dump Jason and stay with Vince, but then the unthinkable happened - he took his shirt off, revealing the ultimate Hugo Boss physique.
Vince’s firefighter instincts kick in when they share a picnic that includes candles, and he states he couldn’t be with someone who would “have an open flame in the middle of a wooded area.” It’s probably because she was dating another guy at the same time, but whatever you say, Vince.
David
David, David, David. Where would David and Phoebe be if she had never met Mike? This is a question we have to ask ourselves, because David and Phoebe had, hands down, one of the most beautifully tragic relationships on the show. They met and they were perfect for each other…and then his science took him to Minsk.
When he returned, David found out that his shot had already been taken, and there was no chance for him to rekindle his love affair with Phoebe. It’s a shame, really, because David was, in many ways, one of Phoebe’s true loves. However, life does work in mysterious ways, so let’s hope for the best for David.
Mike
Monica and Chandler better take a seat, because Phoebe and Mike are here to claim the title of the most awesome couple in all the land. Played by beloved actor Paul Rudd, we knew we were going to fall in love with Mike the first time we saw him. And Phoebe probably knew too, even if she won’t admit it.
The man proposed to her four times, and was one of the very few who truly loved Phoebe for all that she was, weirdness included. People even call him the seventh friend, is there really any possible contest here? We say no!
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