Rachel was right, the madcap girl Phoebe Buffay should be on Oprah. She’d lived on the streets, thought Einstein was her grandfather, her mother killed herself, grandma said her father was a famous tree surgeon in Burma, she was friends with muggers in New York.

Most notably, Phoebe fell in love with a gay ice dancer and married him because he needed a green card. Before she got married to Mike in a fairytale setting, she had never been in a long term relationship, never celebrated an anniversary. Not every date of hers was bad though, only some were. Here are the bad ones, ranked.

Mike

Even though Phoebe ended up marrying the man of her dreams, Mike Hannigan, their first date didn’t go well. She’d asked Joey to set him up with someone, and he had forgotten. Right before the date, Joey scanned Central Perk for an eligible guy and randomly happened to shout, “Mike!” As destiny would have it, Paul Rudd’s Mike was sitting in the coffee shop and agreed to go along with Joey. When Phoebe found out the truth, she bolted.

We Should Do This Again Guy

The ‘we should do this again’ guy who Phoebe dated once, played a critical role in “The One With The Thumb.” Phoebe seemed sad after the date since the guy had walked her to the subway and told her that. Anyway, it kicked off a conversation about the dating language on the show. ‘It’s not you’ means ‘it is you,’ ‘I think we should see other people’ means, ‘haha I already am.’

Tony

Phoebe breaks it off with Tony because it’s not fun anymore. She doesn’t know if the reason behind it is her or the hunger strike.

Phoebe and Chandler decide to break up with Tony and Janice, respectively, at the same time, the same place. It’s smooth for Phoebe, but Chandler ends up hitting Janice in the eye.

Kenny

Phoebe mistook Kenny, the copy guy, for Ralph Lauren. Or, Kenny told her he was Ralph Lauren to get into her pants. They never dated, but fooled around at the offices of Ralph Lauren. Thankfully, Rachel told Phoebe the truth and the whole thing ended. But here’s the thing: how could Phoebe mistake Kenny for Ralph? Long hair, hacky sack, and a beard? Come on!

Roger

Roger was the meanest date Phoebe ever had. He was a psychoanalyst who analyzed her friends and tried to break them apart in the process. She called him sweet and complicated. But he was just intense and creepy. He said Ross married a lesbian to make Monica look like less of a failure in their parents’ eyes. Roger gave Phoebe an earful but he left at the end. His best line was when he said the mugs at the coffee house should have nipples on them!

Carl

Carl was the guy who ate chalk! Phoebe said it herself in “The One Where It All Began.”

This was after Monica announced that she was going out with a guy, Phoebe interjected her by saying, “Wait, does he eat chalk? Just because I don’t want her to go through when she went through with Carl.”

Gary

Phoebe is the type of person who has issues seeing Christmas trees cut down in their prime. She raises rats, she wishes for good things for the rain forests, and world peace. Yet, Gary the NYPD officer failed to see through her. Things were breezy between the two, they even moved in together. He called her baby doll for crying out loud and the chemistry was sizzling. But once he shot a loud bird through their window, everything went down the pooper.

Vikram Mookerjee

Vikram wasn’t a boyfriend or a date but someone Ross made up. Ross had upset Phoebe by telling her she’d never been in a real relationship, right before her first date with Mike. She ended up acting weird on her date. Long story short, Ross blamed himself for the fiasco and went around broadcasting Phoebe’s truth like an unstoppable moron to four different people named Mike.

Phoebe learned Ross had gone to actual Mike’s to tell him how great she was and lied about her 6 year-long relationships with a guy named Vikram! Vik was a kite designer who used to date Oprah, a glue sniffer on the side, and he’d just had a baby with Rachel.

Parker

Alec Baldwin’s Parker was basically Santa, high on Prozac, getting laid in Disneyland. Phoebe met the guy after her creepy date with Jim Nelson. Because of Jim, she had to change her dry cleaners, bank, and grocery store. She was still hung up on the idea that the universe was giving all these signs for nothing.

Parker complimented Phoebe at Bleecker Street Dry Cleaners. At first, she was thrilled to see him, but his motormouth personality killed the relationship. While driving to the Geller’s anniversary, he called the expressway ‘a concrete miracle.’

Larry

At first, Phoebe was excited about Larry’s power to shut down restaurants, but after a while, it got too real. The health inspector kept closing down all of Phoebe’s favorite places to eat. Phoebe had to end this one. Larry was an overworked guy, who was about to shut down Central Perk for health violations. Thankfully (?) Phoebe dumped him in the nick of time.

Robert

Robert, the no underwear guy, was asked by Gunther to put the mouse back in the house. He was an athlete who played sports all the time but didn’t cover his junk. He wore no underwear and his private parts were constantly on display. Duh! If only he’d realized it on his own or had someone discreetly tell him.

Tim

Tim was a sous-chef who works under Monica. Phoebe bumped into him at the restaurant and asked him if his pesto was the besto.

They both are single, he gets off work at 11, she waits for his call. Tim is sweet and calls Phoebe all the time. And if she doesn’t pick up the phone, he comes over. Monica wants to fire Him and Phoebe wants to dump him at the same time. Phoebe breaks it off, but Monica gives him another chance.

The Noisy Guy Upstairs

Rachel and Monica have a neighbor upstairs who’s really loud when he has female company over. He’s really charming, though. Phoebe tells the girls she’s going upstairs to ask him to keep it down but ends up getting intimate with him. Phoebe thinks she and the noisy guy have some kind of a relationship until she hears him make out with another woman. On a side note, he’s so charming, he ends up schmoozing up to Joey, Ross, and Chandler.

Malcolm

David Arquette’s Malcolm was a stalker on Friends. He thought he was stalking Phoebe’s twin Ursula, while in reality, he was stalking Phoebe. Malcolm was the textbook stalker, with binoculars, a journal, and night vision goggles. Phoebe was crazy enough to get involved with her sister’s stalker and thought he was a nice guy. He couldn’t stop stalking Ursula, though. Phoebe caught him and that was that.

Eric

 

Speaking of Ursula, Phoebe actually got involved with her sister’s ex-fiance, Eric. Ursula and Eric were engaged and about to be married. Sean Penn’s Eric and Ursula were invited by Phoebe to Monica’s Halloween party. Phoebe developed a crush on her sister’s fiance. Eric dumped her after Phoebe told her she’d outrageously lied to him about being a teacher and working in the Peace Corps. Eric went out after Phoebe and slept with Ursula again thinking she was Phoebe. Ew.

Jim Nelson

Wouldn’t call anyone worse than Jim Nelson. Jim and Phoebe went out on one date only, thank God! Jim was a creep who wrote erotic novels for children. Phoebe did give him the benefit of the doubt, but when Jim said he had a Ph.D., meaning a pretty huge ****, Phoebe walked the hell away!