The relationship between Monica and Chandler is the strongest throughout Friends, with the two of them being the perfect match for one another. However, Monica goes through plenty of other relationships over the course of the series, with some being heartfelt and emotional, and others being very brief and forgettable.

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She dates a real range of people during her life, and with that comes a variety of personalities and intelligence as well. Some of her partners are smart people, who can hold a conversation and are engaging, yet others are the complete opposite, which makes viewers wonder how Monica ends up dating them in the first place.

Chip Matthews

Friends Chip Matthews and Monica Geller on a date

Chip Matthews was the least intelligent person that Monica ever dated, with her high school crush seemingly still being stuck in the past. The way he acted was as if he had never matured past the point when Monica first knew him, which left their date a very awkward one.

It was clear that they weren't going to work out as a possible pair, simply because their conversation was so poor. He was arrogant and tried to rely upon his looks, seemingly just as he had done in his younger years, not picking up any real-life experience along the way.

Julio

Friends Julio the Poet

On the surface, Julio seemed like he was a lot more intelligent than he actually was. His attempts to write poems weren't perfect, but he was at least trying to be romantic and it did show some serious intelligence in comparison to some of her other partners.

However, the fact that his poems are actually a bit insulting, with Julio deeming her to be an empty vase was not exactly a sign of intelligence on his behalf.

Paul

Paul the wine guy and Monica talking in Friends

Better known as 'Paul The Wine Guy,' he is someone fans certainly did not like due to his sleazebag personality. The way he treated Monica throughout their time together was certainly not positive and certainly did not speak to his intelligence.

Instead, his behavior towards her was truly bullying. Paul was the type of person who felt that he was smarter than he actually was due to his own self-importance, and while he wasn't Monica's least intelligent partner, he was nowhere near as clever as he believed.

Bobby

Fun Bobby talking with Monica - Friends

Bobby was more or less a normal guy during his time with Monica and mostly liked to tell funny stories.

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However, when it becomes apparent that Bobby has an alcohol problem, many fans were proud to see him seek professional help. Many also thought that Bobby prioritizing his mental health was a very mature and intelligent decision, as he told Monica that he couldn't be with her because he didn't feel it was the right time for them to be in a relationship. With a high degree of thoughtfulness, it's possible that he could have been one of Monica's most intelligent dates.

Alan

Monica and Alan standing together in the apartment on Friends

While Monica didn't have the spark for Alan that was needed for this relationship to ever work, there's no doubt that he was a hit with the rest of the group. Everyone loved Alan, which is because he was very charismatic and personable.

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Alan showcased real intelligence throughout his appearance on Friends, with his charm being a real sign of smartness. He knew how to deal with every situation and his ability to engage in brilliant conversations showed he was a bright person.

Timothy

Friends Monica and Timothy together

Being the son of Richard Burke, it was no real surprise that Timothy is intelligent, as that is one of the key traits that his father has too. As an eye doctor, he certainly thrives within his work, and that showcases an impressive side of himself.

But the conversations that he has with Monica during their time together are also a sign of how smart he is. Timothy always conducts himself well, but unfortunately, things are just far too awkward for them to possibly ever work.

Chandler

Chandler in a bath Friends

While Chandler certainly brings out a lot of jokes throughout the show, that doesn't mean that he isn't smart. Sure, he uses comedy as a defensive tactic at points, and he loves to make others smile, but the fact is that he's an intelligent person overall.

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His job is quite the mystery throughout the series, but it is very clear that it's not a simple one to have and he has to put in plenty of work to succeed in that. He's also very smart with how he deals with tough moments in their relationship, always working hard to keep Monica happy. Though Monica ends up with him so he's not technically her ex, he gets an honorary mention on this list.

Richard

Richard and Monica dancing and breaking up on Friends

Richard is the 'nearly-man' for Monica, with who she is very close to settling down with, with just a couple of details standing in the way of them being together. However, his intelligence absolutely is not one of those, as Richard is one of the smartest men to appear on the show.

Richard is much older than Monica, which is ultimately a stumbling block due to him not wanting children. However, it does mean that he benefits from a lot of experience, and it's clear he's very wise, with his conversations with Monica being deep and heartfelt throughout their relationship.

Peter

Monica kisses Pete

Peter is the richest character that ever appears on Friends, as a multi-millionaire, he is able to provide Monica with a totally different life. However, he doesn't just have all of that money for no reason, he works hard to get that by being working in computer software.

Peter is clearly incredibly successful at his work, and it takes real intelligence for that. But he is also very smart within social settings, which is clear whenever he interacts with any of the group. Although, his decision to get into MMA is one that isn't the smartest, which ultimately leads to their break up.

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