14 Of Monica's Boyfriends From Best To Worst

When we first meet Monica Geller in Friends' 1994 pilot episode, she’s an unlucky in love, single woman in New York. And, what do single New York girls on TV have throughout their single years? A lot of boyfriends. Monica was an early sex-positive, single woman on TV, sleeping with Paul the wine guy on the first date in the pilot episode. (Fun fact: The one-night stand was a decision show co-creator Marta Kauffman fought for.) Sex positive woman that she was, Monica stille desired something more from her early bad relationships. She wanted a husband and family, which she gained in a friend throughout the second half of the show’s 10-season run.

Monica was always honest about her desires, what she wanted out of a relationship, and with her grief after they ended. Monica’s first encounter with Paul, left us rooting for her from day one and her relationship with Chandler was more satisfying than fans could have predicted. But, between Paul and Chandler, Monica had to kiss a few frogs before she found her prince. Well, more than a few, but definitely less than a “ballpark.” Here is the definitive ranking of all the men in Monica’s life throughout the series from worst to winner.

14. Paul The Wine Guy

Paul lied to Monica about being impotent, a line he apparently used a lot, in order to get her to sleep with him. So, naturally, she broke his watch.

Paul’s Rating: Total Sleaze

13. Julio

Julio is the poet/busboy Monica dated during her stint at the themed diner. He famously wrote the insulting poem, “The Empty Vase.” Monica thought it was about her being vapid, shallow, and empty. To which Julio explained, it’s not about Monica, per se. It’s about all women.

Julio’s Rating: Misogynist

12. The Coma Guy

The Coma Guy was less of a love interest and more a source of competition between Phoebe and Monica, who both felt mildly responsible for his coma. Though it was creepy that they invested so much effort into this John Doe, I can’t help but feel he was unappreciative of their gifts and devotion to his comfort when he woke up.

Coma Guy’s Rating: Selfish/Sleepy

11. Bob

Joey creates a ruse to get back with his ex-girlfriend by telling said ex that Monica is his current girlfriend and Monica that the ex’s new boyfriend, Bob, is Joey's ex's brother. Oh boy. This leads to a double date that could only happen in the sitcom universe. Before it gets too excruciating, Monica figures it out and Joey and Monica get the respective girl and Bob.

Bob’s Rating: Too Complicated

10. Jean-Claude Van Damme

Once again, this situation is less about love and more about competition between Monica and Rachel. The two eventually get into a fight where they destroy each other’s belongings. Learn from this, you guys.

Jean-Claude’s Rating: Not Worth It

9. Timothy Burke

Richard’s son. That’s all I have to say about that.

Timothy’s Rating: Creepy

8. Ethan

Ethan and Monica lie about their age. Ethan’s lie is just a little bigger than Monica’s… because he is actually in high school.

Ethan’s Rating: Jailbait

7. Chip Matthews

Monica finally gets to date her high school crush — only to find out he never really left high school. Sometimes, it’s better to have the fantasy.

Chip’s Rating: Man Child

6. Roy Gublik

Monica's prom date who wanted to kick Chip's ass for being late.

Roy's Rating: Saw Star Wars 317 times

5. Fun Bobby

When Monica realizes Fun Bobby is only fun because he is an alcoholic, the party is way over.

Bobby’s Rating: Not-So-Fun Bobby

4. Pete Becker

Pete romantically pursued Monica and whisked her off to Italy on the first date. But, in the end, he chose UFC fighting over his well-being, and Monica couldn’t watch him get hurt.

Pete's Rating: Too Intense

3. Alan

Everybody loved Alan... except Monica.

Alan’s Rating: Seems Like a Nice Guy

2. Richard

Monica’s first big love on the show. Despite the age difference, they were great together. They had fun together, there was chemistry, and he already knew her parents. OK, that last one may not be a pro. But, Richard had already raised children and Monica had to be honest about what she wanted.

Richard’s Rating: The Personification of Heartbreak

1. Chandler

Chandler is Monica’s best friend. They love each other deeply and make each other better people. What else can you ask for in a partner?

Chandler’s Rating: #RelationshipGoals

Images: Warner Bros. Television (11); Giphy (1)