Every Love Interest Of Friends' Monica Geller, Ranked

Out of the six main characters on "Friends," Monica Geller (Courteney Cox) is undoubtedly the best friend. She lets Rachel move in with her after not talking for years, she always hosts holiday events and cooks for the group, and she genuinely takes the time to care for everyone. That's not to say that the other characters are bad companions, but Monica definitely goes above and beyond where some of the others wouldn't. For 10 seasons, fans watch as Monica remains the glue of the iconic group.

With such a big heart, though, it stands to reason that Monica would make some poor dating choices. She cares about people so much that it's easy for her to get swept up in the romance or magic of relationships when it's not in her best interest. However, every experience she has only helps her grow and mature, whereas other people might struggle to see the lessons that come from past flings and relationships.

Monica fans will remember some of her more questionable partners, and her few really great choices. Read on to see every one of Monica's flings and boyfriends ranked from worst to best.

Monica dates a lot of bad guys, but Julio is definitely at the bottom. Monica and Julio (Carlos Gómez) meet in Season 3 when they're both working at the Moondance Diner. He's a sensitive, charming poet who writes Monica a verse while they're together. When Monica shows it to her friends, though, Phoebe picks up on the fact that the poem, "The Empty Vase," is talking about how Monica is only a surface-level human and can't really go deep intellectually. Monica confronts Julio about it, but he denies that it's about her. However, the other shoe drops when he tells her the poem is in fact about all women, specifically American women. Monica then hires a barbershop quartet to come into the diner and sing about how terrible Julio is.

At first, Julio is nice to Monica, but he quickly turns from charming to misogynistic. For him to make a generalization that all women are shallow is incredibly misguided and Monica is much better off without him. Since Monica also points out that Julio is bad in bed, there seems to be nothing going for this man once you get to know him.

It's never really explained why Paul (John Allen Nelson) is called "Paul the Wine Guy," but that's what the group refers to him as. Whether he sells it, drinks it, or just talks about it a lot, the name sticks. He appears in the first episode of "Friends" where Monica is out to dinner with him. She doesn't initially consider it a date, but mostly just to keep her hopes low around her friends. While they're on the date, Paul tells her that ever since his wife left him, he hasn't been able to perform in the bedroom. Monica thinks this is endearing, and the two sleep together. However, when Monica talks to her co-worker, she realizes that this is a line that Paul uses on women in order to scheme them into sleeping with him. Monica is furious and ends up breaking his watch.

For a guy to manipulate women to sleep with him is low in and of itself, but for a guy to use this tactic of making a woman feel special and safe with him only to be doing it to every woman he meets is even more pathetic. He and Julio are pretty close in ranking because though Julio admits to his misogyny, Paul is riddled with it, too. He's definitely not worthy of Monica, and good for her for breaking his watch.

Yes, it might seem strange that Belgian actor Jean-Claude Van Damme is on the list, but for those who forgot, they really did date in the show. Monica sees the actor while the friends are on set of Ross' pet monkey Marcel's movie in Season 2. Monica admits she's attracted to Jean-Claude, and though Rachel encourages her to go and talk to him, Monica is too shy. Rachel decides to help her friend and asks him out on Monica's behalf. Unfortunately, though, Jean-Claude doesn't want to go out with Monica; he wants to go out with Rachel, and she agrees to the date. Monica gets upset about it, and Rachel agrees to bow out and let Monica go on the date. Jean-Claude tells Monica that the only reason he agreed to go out with her is that Rachel told him Monica was willing to have a threesome with him and Drew Barrymore. Monica obviously refuses this, and they don't go out again.

The fact that Jean-Claude is only interested in Monica when he finds out she wants to have a threesome is weak. He should've given it a chance, but it's hard to fault him for not wanting to go on a blind date with someone who appears to be a crazed fan. That's the only reason he ranks higher than other men on this list.

Ethan (Stan Kirsch) and Monica date in Season 1. When they meet, Ethan tells Monica that he's a senior in college and Monica says she's 22, even though she's 26 at the time. Everything goes well until the truth about their ages comes out after they sleep together. Monica confesses first before Ethan admits that he also lied about his age. The problem is, he reveals that he's not a senior in college, but actually a senior in high school and is 17 years old. He wants to continue the relationship, but Monica thinks it's too gross because of how young he is, so she decides to end the relationship.

Their age gap is nearly ten years, and Ethan is a minor. There was no way the relationship could work out, but it's still very gross that both of them felt the need to start the relationship with a lie. That's not a good foundation to begin any relationship, especially because the lie is about age and, to Monica's point, Ethan's lie made her a felon in most states. It's not that he's not a good person, he is just too young for her.

Chip (Dan Gauthier) actually appears in two episodes of "Friends." First, in Season 2, we see him as Rachel's date to her high school prom. His second appearance comes in Season 4  where he runs into Monica and asks her out on a date. She decides to go out with Chip but realizes he is still incredibly stuck in high school and has not matured a day since. He still lives with his parents, he still works at the same job, and he still has the same friends who do the same immature acts. The only good part about the date is that Monica ends up getting to dump Chip and reject him instead of the other way around.

Realistically, Chip should be lower, but he didn't have any fundamental issues that made him that bad of a person. His only real fault is being immature. It is definitely a superficial matter when Chip only wants to go out with Monica now that she's skinny and didn't notice her when she weighed more in high school. It's also very awkward to go out with your friends' ex-boyfriends, so there was likely no chance Chip and Monica would have worked out.

Phoebe and Monica see a cute guy (David Sederholm) walking down the street, and Phoebe gets Monica to whistle at him. When he turns around, he is hit by an ambulance that knocks him into a coma. Feeling so much guilt about the incident, Monica and Phoebe try to take care of him while he's in the hospital even though they don't know him. They spend the time fantasizing about what he might be like in real life until he finally wakes up. They tell him that they've been taking care of him, but he doesn't have many thanks to give because he doesn't know who they are. Monica and Phoebe are angered by this lack of appreciation, and they leave.

First of all, the fact that they refer to him as "Coma Guy" is reason enough for him to rank lower on the list. There is no real foundation for this relationship and it's not based on any mutual attraction or interests in common, only the idea of him in Monica's head. Plus, she and Phoebe felt the need to battle over this man, which is usually a sign that both friends should respectfully bow out instead of letting it ruin their friendship. He's not very nice when he wakes up, but it's hard to blame him. It's creepy to have someone you don't know around you while you're in a coma.

Alan (Geoffrey Lower) is an interesting ex-fling because there's not a lot wrong with him other than the fact that Monica wasn't as into him as the friends were, and he wasn't as into the friends as she hoped he would be. Monica is worried about bringing Alan to meet her friends because she has a track record of the group not liking her dates. However, they immediately love Alan and are proud of Monica's choice. Monica starts to become fed up with Alan and feels like they're not meshing well, but the friends love him so much that she tries to stick it out. She ends up breaking up with Alan, and the group is devastated. However, as it turns out, Alan hated them anyway so it is good that they're not together.

Monica clearly didn't like him as much as she should have for it to be a good relationship. It's good that Monica made the healthy decision to break up with him, even though her friends all liked him. As important as Monica's friends are to her, whoever she dates needs to like them, or else it's a deal breaker. Monica and Alan are both better off with other people.

While Monica's ex-boyfriend Richard is out of town, his son Timothy (Michael Vartan) fills in as an eye doctor. Monica goes in thinking she's going to see Richard, but it's Timothy she meets instead. Monica invites Timothy to have Thanksgiving with her and her friends, and it's clear that they are both attracted to each other. All of her friends immediately see the warning signs and tell her that the situation is weird. Monica doesn't listen, and when she and Timothy kiss, Monica is reminded of Richard. Both of them are freaked out and decide things can't go any further between them.

Timothy and Monica were never going to work out. It's impossible to date the child of your ex and have it be completely normal and have no underlying weirdness. Timothy is a nice person, and maybe in a different situation he would have been a good match for Monica. But it's impossible to tell because it will always be weird seeing that he is Richard's son. Monica and Timothy shouldn't have even tried the relationship in the first place, but it's good that they were able to end things.

Fun Bobby (Vincent Ventresca) and Monica date on and off throughout the first and second seasons of the show. He first appears as Monica's date to her New Year's party and is known for being a fun guy. However, when he first shows up, he's distraught by the death of his grandfather and isn't much fun at all, despite his name. In the second season, Monica and Bobby get back together, but she figures out that he is an alcoholic. Monica has a heart-to-heart with Bobby and tells him that she's concerned for his health, and he decides to give up drinking. The problem is, the friends realize that Bobby is only fun when he is drinking, because when sober, he becomes boring. Monica and Bobby break up because Monica starts to drink a lot more so she can be entertained by Bobby. He tells Monica his sobriety can't handle being with someone who drinks that much.

Bobby is a good person and when he is fun, he is a good match for Monica. He gets along with her friends and always prioritizes her happiness, but for him to only be fun when under the influence isn't healthy. He needs to focus on himself and getting better before he can be in any relationship.

Monica's top three relationships are the easiest to rank. In third place is Pete (Jon Favreau), Monica's serious boyfriend whom she meets while working at the Moondance Diner. He is a customer there and asks Monica out after hearing her complain about not having any dates. She says no, and he tips her $20,000, which leads to Monica figuring out that he is a millionaire manager of a computer company. She accepts his offer, and they have an amazing first date. He is perfect in every way, except for the fact that Monica isn't attracted to him. 

Eventually, she does fall for Pete, and they engage in a full-blown relationship. However, when Monica thinks that Pete is going to propose, he actually tells her that he's training to become the Ultimate Fighting champion. Monica tries to be supportive, but after seeing him in two fights, she tells him she can't sit by and watch him get hurt. UFC comes between the couple, as Pete decides to prioritize it, and they break up.

Pete is a kind person who cares about Monica a lot. If UFC hadn't come between the couple, it's very possible that they would have gotten married. Monica could have lived a comfortable life and pursued her dreams while Pete financed them, but ultimately they wanted different things, and the relationship ends for Monica's benefit.

In second place is Dr. Richard Burke (Tom Selleck), Monica's almost-perfect match. Richard and Monica have known each other Monica's whole life because Richard is good friends with her parents. They meet again as adults when Monica and Phoebe cater a party of his. Monica and Richard immediately hit it off and it's clear their chemistry is going to materialize into a relationship. The two get through telling Monica's parents about their relationship (and the age difference), and Richard is able to win over Monica's friends. 

However, they break up because Monica wants to have children and Richard doesn't, and only would to keep Monica in his life. It takes her months to get over the relationship, as she is devastated by the breakup. However, she runs into Richard at the store, and they strike up another fling. Richard wants to get back together, but Monica knows that nothing has changed. From there, the two remain distant friends, and the relationship never rekindles.

Richard and Monica would've gotten married. Their age difference is slightly awkward, yes, but they are both adults and could have made it work. Richard just doesn't want kids and Monica does. Otherwise, they are perfectly matched — they have great conversations and chemistry, and they are interested in a lot of the same things, but more importantly, they love each other more than anything.

In first place is Monica's perfect match: Chandler (Matthew Perry). Chandler and Monica have a close friendship throughout the first four seasons until they get together. While in London for Ross' wedding, they start a secret relationship that only Joey knows about for a while. However, once they finally tell all of their friends, everyone is on board and agrees that they're a great couple.

Eventually, Chandler and Monica propose to each other, and they get married. They go through some hardships after they find out Monica and Chandler aren't compatible biologically but they find an excellent surrogate mother and end up having twins.

Chandler and Monica have something in particular that none of her other relationships had: they were friends before they started dating. Because Monica and Chandler build a solid friendship foundation, it makes it much easier for the two to transition into a romantic relationship. Monica loves Chandler's jokes and his entire personality, and Chandler loves all of Monica's quirks and who she is as a human being. They teach each other how to mature and handle all of life's stresses, and they make each other stronger and better as people. Simply put, Chandler and Monica are at their best when they're together, and who could ask for a better relationship?