Monica was the friend who just couldn’t wait to stop dating and marry the man who would become the father of her children. We only saw Monica in the dating scene from the first season to the fourth season, but she was in such a rush to get married that she has a very sizable history of relationships.
Since Friends is a sitcom, some of Monica’s relationships were played for laughs and were very short-lived; these can’t really amount to much but they do still count. Monica did have some boyfriends who were integral to her story, and they are rightfully included in this list as well. We’ve counted those relationships here where Monica was seen going on at least one date.
10 Timothy Burke
To be fair, Timothy was a nice young man who had nothing wrong with him. So why is he at the bottom, you ask? That would be because he’s the offspring of one Richard Burke – the guy Monica was very close to marrying!
Monica and Timothy could’ve gotten married and had children and we’d still put him at the bottom of the list because it’s pretty gross how they were involved; a sentiment shared by all the friends as well. As it happened, their relationship consisted of just one date and a solitary kiss before Monica was reminded of Timothy’s father’s similar kissing skills and was too disgusted by the whole thing; eventually calling it off.
9 Paul the Wine Guy
Paul lands close to the bottom position for being such a bad guy who manipulated Monica. He seemed to be a dreamy catch until it was shown he’d lied about losing his wife and only used it as a line to get Monica into bed.
Their dating history consisted of just the one date, which went really well and Monica had high hopes. But after she discovered his deception, she broke the relationship, and Paul’s watch, off for good. Paul doesn’t deserve any further mentions other than this one and we hope he ended up all alone for playing Monica like that.
8 Chip Matthews
How can you expect a relationship that comprised of the guy going on and on about his high school exploits to rank higher? Well, you don’t, and Chip is thrown near the bottom of the pile. At least he wasn’t deceptive to Monica, which is why he’s not completely in last place, but the date he had with her was lousy.
Chip was an overgrown manchild who had the same job since he was 18 and still lived with his parents (although he could stay out as long as he wanted), and Monica wasn’t impressed. Still, she didn’t think the relationship was a total failure as she took pride in the fact that she got to both date and dump the jock of her high school class.
The time Monica spent with Julio was short but passionate, and she was enjoying herself until Phoebe’s oddly perceptive reading of Julio’s writing squandered everything. Julio turned out to be a guy who was high-minded about his abilities and didn’t respect women, and it got him dumped by Monica as a result.
It wasn’t a complete disaster, however, as Monica did get to jump on the guy whom she was insanely attracted to, and she didn’t seem at all shattered at the break-up. Turns out a physical relationship was a good thing for her at the time when she was at a low point in life. But Julio wasn’t a good boyfriend by any means.
6 Young Ethan
Now we arrive at the guys who weren’t bad boyfriends, but just lacked the timing – in the case of Young Ethan, that’s really saying a mouthful. You see, even though Ethan must be in his forties by now, he’ll always be called “young” as we only saw him as a high school senior.
He and Monica had a lovely relationship which was satisfying both emotionally and physically; the only problem was he was in single-digit age when Monica had been his age. Ethan was genuine in his feelings, but Monica couldn’t look past the fact that she was almost a decade older. As said before, timing was too bad and it’s too bad they didn’t reconnect years later.
5 Fun Bobby
Fun Bobby seemed to be the boyfriend everyone would want. He was handsome, very likable, and the life of the party. Monica always had fun with him – hence the name – and these two were amicable even when they weren’t together. Monica would certainly rate him as a good boyfriend, but the problem is his “fun” aspect relied too much on the bottle.
They became increasingly co-dependent on each other and it just wasn’t too healthy in the long-term. Everything was okay, but sometimes people just need to stick to their vices to have their true personality, and Monica just couldn’t accept Fun Bobby for his vice. Still, there was never any acrimony here.
On the outside, there was absolutely nothing wrong with this relationship. Alan, for all intents and purposes, was the perfect guy. Unfortunately, Monica didn’t have any feelings of chemistry for him and let him go.
He ranks high, however, because there was literally nothing wrong with this guy. Everyone loved him and he was the soul of the group for a time. Had Monica felt romantically toward him, Alan would’ve married her long ago. We won’t place him in the top-3, though, as Alan only had the one appearance and he didn’t like the friends group at all, even though they were obsessed with him.
3 Pete Becker
They openly stated they loved each other and Monica wanted to marry him. The problem was he probably saw Monica more as a conquest for victory than a potential spouse and the two broke up very tamely in comedic circumstances. Still, Pete makes it in third position because he was awesome and his relationship with Monica was a happy, loving one – until he became obsessed with getting walloped in the UFC.
2 Richard Burke
Relationships with big age gaps are never shown in a positive light on TV; Monica and Richard were the first exception to this rule. They were a superb couple as they were both the mature ones in the relationship as opposed to one being childish while the other being the responsible one.
Monica always did seem mature beyond her age, which is why she gelled so well with Richard. It was only because he wasn’t willing to have kids that they broke up; other than that, there were no problems with these two. In another life, they would’ve been a long-married couple by now.
1 Chandler Bing
Sure, Chandler was like a kid, but it was the sheer development in personalities for both concerned that makes Monica and Chandler the best couple Monica was in. She was too shrill and uptight in many regards until she had a man like Chandler who tolerated her quirks thanks to his easy personality.
Monica also craved a relationship where she was the giver, and she did just that with Chandler who finally found a person willing to put up with his insecurities. The best relationship you can have is with your best friend, and these two were proof of that. They got together at the right time and everything about them made perfect sense. As fate would have it, these two were meant to become parents to twins we know they loved more than anything else.