An Official Ranking of Every Boyfriend Monica Had on 'Friends'

Julio was a misogynist dressed up as a romantic. He was Monica’s rebound from her relationship with Richard, and boy was he sexy, but comparing women to an empty vase means that you deserve to be hit over the head with one. He still ranks above Paul because at least he put his jerkiness in writing.

Ahh, Chip — the kind of guy Monica always wanted to date in high school. Unfortunately, the alpha male in high school doesn’t age very well — he still works at the movie theater and lives with his parents. (But don’t worry, he can stay out as late as he wants.) Chip would be fun for a stroll down memory lane, but he’s so stuck in the past that he’s far too sad to date.

Also known as “young Ethan,” he was the 18-year-old that Monica accidentally started dating. (He told her that he was a senior in college, she told him that she was 22.) Ethan was sweet and well-meaning, but there relationship was waaaay too icky for words. Unless that word is “ick,” of course.

Fun Bobby was SUPER fun… when he was hammered. Bobby is the kind of guy you date when you’re in a rut and want someone to shake up your life. Unfortunately, once Bobby stopped drinking, he was kind of a boring mess — which means that the real Bobby was a boring mess. You should never date someone you can only be with when you both have a glass of wine in hand — but at least it was fun while the buzz lasted.

Timothy is Monica’s ex-boyfriend Richard’s son, so is closer in age to Monica than his father, who is 21 years Monica’s senior. But their similarity in age didn’t make them a good match. Timothy was a hot eye doctor who could have been a good fit for Monica, but how he supposed to work with knowing that his father dated her first?

Poor Alan. He was so great! So funny! All of Monica’s friends loved him! Unfortunately, Monica didn’t feel the spark — and Alan didn’t feel one between him and her friends. Sometimes it just doesn’t work out, but Alan ranks higher than the other guys because he actually seemed like a genuinely good guy without the complications some of the other guys lower on this list had to deal with.

I liked Pete. He was kind of quirky, fun, and genuinely cared about Monica. He pursued her relentlessly, knowing that there was something between them before even she did. Sure, it’s not always the best tactic, but in this case, he was right… and the only thing that broke them up was his desire to be the Ultimate Fighting Champion. Pete loses points for hubris, but I like to think of that as just another one of his quirky flaws.

Obviously, Richard’s name ranks highly on this list. Monica and Richard seemed doomed from the start (I mean, Monica’s judgmental parents are RIchard’s best friends) but this couple built a solid relationship despite the obstacles. Ultimately Richard and Monica broke up due to bad life timing — Richard didn’t want to have another kid, and Monica couldn’t fathom not having a family of her own — but both cared enormously for one another. I’d say it was a shame that these two didn’t work out, if not for the last person on this list…

Well, obviously. Monica and Chandler were strictly platonic for the first four seasons of Friends, but got together after a tryst in London in Season 5. How they didn’t see that they were so clearly meant to be for nearly 100 episodes is outstanding to me, but I’m glad that they finally saw the light. The show ended with the married Monica and Chandler adopting twins and moving to Westchester — exactly how most New York City love stories end.