Bad Taste in Men: Ranking Friends Phoebe's 5 Creepiest Dates

Over the course of ten seasons of Friends, Phoebe dated a lot of guys before finally settling down with Paul Rudd's Mike Hannigan. Some of the guys were nice and even remarkable. But some were downright disgusting. Here are the five grossest men Phoebe dated on the show, ranked by how creepy they are.

5. Roger aka the Psychiatrist

In Episode 13 of the first season of Friends, Phoebe met Roger, a talented psychiatrist who could tell you your entire life just by observing you and then deducing and deconstructing your problems. While fun at first, Roger turned out to have no respect for people and their feelings, criticizing Phoebe's friends and enjoying his perverse power over others. To top it off, he saw sexual meaning in almost everything in the best (or worst) Freudian way.

4. Malcolm aka the Stalker

In Episode 3, Season 3, Phoebe confronted her longtime stalker, Malcolm, who turned out to have mistaken her for Ursula, Phoebe's estranged twin sister. After learning that it wasn't her he was stalking, Phoebe mellowed out and started dating him, which is a very disturbing thing in itself. The creepiest thing about Malcolm is that he continued to stalk Ursula while dating Phoebe at the same time, which led to their breakup.

3. Robert aka No Undies Guy

Compared to the previous guys on this list, Robert, whom Phoebe met in Episode 13, Season 3, might seem quite nice. He was cute and friendly, and the only thing wrong with him was that he didn't wear underpants. Sure, you might interpret it that way, but if you watch the episode again and pay attention to how demonstrative Robert is about not having underwear on, you'll see that he's sex-offender-ishly creepy.

2. Eric aka Ursula's Ex

You might think that Ursula's ex, Eric, who came into Phoebe's life in Episode 7, Season 8, isn't as creepy as Malcolm. After all, Eric wasn't stalking Ursula, he was her fiancé. But when you realize that the only reason he approached Phoebe in the first place was because of her two-peas-in-a-pod resemblance to Ursula, you realize what a creep he was.

1. Jim Nelson aka the Author of Erotic Novels for Children

Without a doubt, Phoebe's creepiest date was the guy who frequented Central Perk and whom she finally decided to approach in Episode 17, Season 8 after her tea leaf reading said that she would meet the man of her dreams. Jim turned out to have a P.H.D. (note the spelling), which stands for 'a pretty huge d*ck.' But worse than that tasteless and disgusting pun, he wrote erotic novels for children. What else is there to say?