Everyone Monica From "Friends" Dated: Ranked From Absolutely Undatable To Marriage Material

It doesn’t get any worse than Paul the Wine Guy.

Before Monica and Chandler’s epic love story began, she dated her fair share of men.

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Here are all of Monica's love interests rated, in my eyes, from worst to best.

17. Paul the Wine Guy

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I think we can all agree that Paul the Wine Guy was bad news. He lied to Monica about being impotent to make her feel sorry for him and get her into bed! The worst part is he’d used that line on countless other women before. Throw the whole man away. 

16. Julio the Poet

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Shortly after Monica and Julio started dating, he wrote a poem that revealed his true colours… That he's a raging misogynist. At first, it seemed like The Empty Vase was about Monica, but he later confirmed that it was about how shallow ALL American women. And who said romance was dead? 

15. Chip Matthews

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Chip cheated on Rachel a number of times when they dated in high school. Despite this, Monica had a huge crush on him and in season 4, she finally got the opportunity to date him. She soon realised that he's the exact same guy he was in high school right down to his movie theatre job, jock friends, and inappropriate sense of humour. Some things just never change. 

14. Young Ethan

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Although these two had heaps of chemistry, their relationship was doomed from the start. They lied to each other about their ages, but Ethan’s lie was significantly worse. He claimed to be a senior in college when he was only 17 years old! He adored Monica, but he was also willing to put her at risk of being charged with a very serious crime. If that’s not a dealbreaker, I don’t know what is. 

13. Jean-Claude Van Damme

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Jean-Claude only agreed to date Monica because Rachel told him that she wanted to have a threesome with him and Drew Barrymore. Unfortunately, Jean-Claude was far more interested in sleeping with Monica than actually getting to know her. 

12. The Coma Guy

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So Monica never actually dated Coma Guy, but she did fight with Phoebe over the prospect of getting to date him. They both went above and beyond to take care of him while he was unconscious but when he finally woke up he was ungrateful, unappreciative, and borderline rude. What a letdown...

11. Fun Bobby

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It turns out, Fun Bobby was only fun when he was under the influence. Monica managed to help him overcome his drinking problem but ended up drinking herself to tolerate his dullness. I think that’s a pretty clear sign that these two were not meant to be. 

10. Stuart

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Cousin Frannie invited Ross to her wedding, but didn't invite Monica. We later find out that she didn’t want Monica there because she used to date her fiance Stuart. While we don’t have long enough to decipher whether Stuart is actually marriage material, the fact that he’s been romantically involved with two cousins definitely doesn't help his case.  

9. Dr. Roger

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Dr Roger is Monica’s boyfriend in "The One That Could Have Been." He was a decent guy but unfortunately, was obscenely boring. He somehow turned every conversation into an unbearable history lesson. Read the room, Roger. 

8. Timothy Burke

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If you can ignore the fact that Timothy is Richard’s son, then he’s a rather stellar guy – charming, polite, and he has a great job. Unfortunately, I can't get over the fact that he is Richard's son, so it’s a solid no from me. 

7. Bob

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Joey wanted to get back together with his ex-girlfriend Angela who was dating Bob, so he orchestrated a double date with Monica in order to split them up. While they succeeded in breaking up the couple, leaving Monica with Bob all to herself, we don’t see enough of him to work out if he’s a catch. He’s definitely not the worst guy that Monica dated though.

6. Mischa

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Phoebe started dating a diplomat who didn’t speak a word of English and his translator Mischa was present at all times. In order to have some alone time while Mischa was around, Phoebe invited Monica along for a double date, as you do. Despite the chaotic evening that ensued, Mischa proved himself to be a stand-up guy. He was chivalrous, respectful, and he had coupons!

5. Roy Gublik

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Roy was Monica’s high school sweetheart. He took her to prom and even brought her a beautiful corsage. He also saw Star Wars 317 times, which is pretty impressive if you ask me. 

4. Alan

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Sadly, everyone loved Alan except Monica. On paper he was the perfect guy but Monica just didn’t feel a spark between them. It’s safe to say that her friends were more heartbroken than she was when their relationship ended. 

3. Pete Becker

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It took a while for Monica to feel any physical attraction to Pete but thank God, she did because they were great together. Aside from being a millionaire with a talking fridge, Pete was a hopeless romantic who would do just about anything for Monica. He even bought her her own restaurant! Even though things didn’t work out between them, it’s safe to say that Pete was a 10/10 guy. 

2. Richard Burke

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Richard was definitely the love of Monica’s life – until Chandler. Despite the 21 year age gap between these two, they were a wonderful couple. Richard pretty much ticked all the boxes for Monica – he was mature, reliable, romantic, had a great moustache, and wasn't afraid of commitment. The only problem was that Richard didn’t want to have any more children which was a huge dealbreaker.  

1. Chandler Bing

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What started off as a meaningless hookup in London turned into the most beautiful love story. Even though Monica dated some great guys before Chandler, there’s no doubt that he was The One for her. 

How do you think was Monica's best boyfriend? Tell us in the comments!