Monica (Courteney Cox) and Chandler’s (Matthew Perry) relationship may have come as a surprise to Friends viewers, but it grew to become one of the healthiest, most endearing, and most admirable relationships in the series. Not every fan loves them, but I would argue they’re the best couple on Friends. Monica and Chandler’s relationship has so many cute moments that go down in history as some of Friends’ best moments. 

They had a rich history both as friends and lovers and then as husband and wife. Let’s look back at Monica and Chandler’s relationship and the moments that defined it.

Click through to read the full story...
By Jerrica Tisdale

During Friends Season 5 Episode 8, “The One With All The Thanksgivings,” we see through a series of flashbacks how Chandler and Monica first met. It was a rocky start as Chandler falsely believed that he was such a prize that he could judge Monica for being fat. The night ends with Monica overhearing Chandler speaking unkindly about her to Ross.

This kickstarts Monica’s weight loss journey. It also kills any chance of romance for them in their younger years.

The following Thanksgiving, Chandler returns to the Geller household and discovers that Monica has lost a lot of weight. He now finds himself interested in her physically, but she’s just out for revenge. This leads to some poor attempts by Monica to be sexy. 

She tries to make a knife seem sexy and accidentally drops it on Chandler’s foot — leading to the permanent loss of one of his toes. This incident further pushes them into the friend zone for many years. 

It seems like maybe the Friends writers decided at the start of Friends Season 4 or the end of Season 3 that Monica and Chandler’s relationship would develop into something more. There are some little hints about the possibility of it throughout Season 4, but the biggest one seems to come during the Season 3 finale and Season 4 premiere.

Chandler proposes the idea that if they’re not seeing anyone in a few years, then they should get together. Monica immediately rejects the idea, but Chandler becomes a little obsessed with proving they would be a good pair. This all goes to hell when a jellyfish stings Monica at the beach and Chandler must pee on her to stop the pain. She states at the end of the Season 4 premiere episode that she will always now see him as the guy who peed on her. 

As we know, that will change by the Friends Season 4 finale. 

Chandler has some insecurities about having sex with his girlfriend Kathy (Paget Brewster) because she used to date Joey (Matt LeBlanc). After their first sexual experience, Chandler doesn’t think he performed as well as Joey, so Monica offers to help him by drawing a diagram and explaining how to pleasure a woman.

This moment is important to the Monica and Chandler relationship timeline because if Chandler hadn’t had this lesson, there is a good chance that they would never have had sex after their first night. Monica and Chandler have both also said they’re the best sexual partners that each other has ever had, so this is a credit to Monica’s teaching skills. 

The Friends Season 4 finale is when Monica and Chandler go the friends-to-lovers route by having sex in London. In Season 7, we learn more about the first night they have sex. Originally, Monica wanted to hook up with Joey but found Chandler instead. 

She needed some comfort after being mistaken for Ross’s (David Schwimmer) mother. Monica sought some no-strings-attached sex. Chandler and Monica were both a little drunk, and Chandler’s kindness won her over. 

The pair then attempts to keep things platonic in the Friends Season 5 premiere by making a pact to only have sex while in London. Once back in New York, they want to pretend it never happened.

However, they’re constantly stopped by interruptions while in London and don’t get to have sex again there. But, Chandler uses that he’s still on London time as a way to still hook up (or "goofing around," as Chandler calls it in a later episode) in New York. Therefore, this starts their epic romance. 

“The One With All The Thanksgivings” is one of the best Friends Thanksgiving episodes and what makes it so special is the final image. It’s the sight of Monica with a turkey on her head. She wears it to cheer up Chandler after he learns how she directly caused him to lose a toe.

After seeing Monica’s turkey dance, he can’t help but laugh. He also accidentally tells her that he loves her, but tries to pretend it didn’t happen. 

A few episodes later, in one of the best Friends episodes, “The One Where Everybody Finds Out,” Chandler admits that he loves Monica. She loves him as well. It all happens because Chandler and Phoebe (Lisa Kudrow) try to outwit each other through seduction. They all know that the other knows that they know. However, no one will admit it.

After Phoebe and he briefly share a kiss, Chandler ultimately gives in. He admits he can’t hook up with her because he loves Monica. 

After their relationship becomes public, Monica and Chandler’s romance goes pretty well until Richard (Tom Selleck) makes an appearance. Monica and he have an off-camera lunch that she hides from Chandler. However, once Chandler finds out, he’s not happy.

This turns their 1-year anniversary Las Vegas trip into a nightmare. However, things take a turn once they talk it out and Monica tells him that she has no feelings for Richard. They use Monica’s winning streak to decide if they should elope in Las Vegas. One of the dice falls to the ground between four and five. If it’s a four, they get married. They decide it’s a four and head to the chapel. 

Monica and Chandler’s plans are overshadowed when they see a very drunk Ross and Rachel (Jennifer Aniston) coming out of the chapel first. They need to decide whether to still get married or not. They look for signs. Most of the signs point them down that path, but they both think it’s too soon.

Once they’re back in New York, they decide to just move in together instead. This once again changes the arrangement of people who lived in Monica’s apartment. 

Unlike Ross and Rachel and the constant breaking up and complications of their relationship, Chandler and Monica have a solid foundation for their romance. This means that it’s inevitable that they get married. During the Friends Season 6 finale, the couple finally makes that move.

However, it’s not an easy road as Richard pops up at their engagement dinner, which prompts Chandler to wait. Also, Richard tells Monica that he wants her back, just as Chandler starts to pretend that he doesn’t want marriage. Lots of miscommunication and Richard’s involvement almost ends Chandler’s proposal plans. 

Nevertheless, the season ends with a very romantic proposal from both Chandler and Monica. 

Monica and Chandler spend most of Friends Season 7 planning their wedding. This includes major engagement milestones, like engagement photos, picking the maid of honor and best man, writing vows, picking a venue and band, and other wedding-related activity. 

Friends Season 7 is very much about Chandler and Monica’s upcoming wedding. 

All the wedding preparations come together during the Friends Season 7 finale. However, before they can walk down the aisle, Chandler gets cold feet and almost ruins the wedding. Luckily, he gets it together enough for them to marry in one of Friends’ most romantic moments.  

During the end of Friends Season 8, Monica and Chandler decide to actively try to have a baby. Unfortunately, their plans get temporarily halted when Chandler accidentally accepts a job in Tulsa. Initially, Monica agrees to move with him, but she then gets offered a dream job in New York.

They work it out where Chandler spends four days in Tulsa and then comes back to New York. The distance puts a strain on their relationship, but ultimately, in one of the not-so-great Friends Christmas episodes, Chandler finally quits his job after he’s forced to work during the holidays.

This leads to Chandler finding a new job that he loves and them resuming their baby-making plans. 

Sadly, by the end of Friends Season 9, Monica and Chandler learn that they can’t conceive together. They decide to explore adoption. It feels like the right move for them.

Friends gets one of its best guest stars when Anna Faris appears in the final season as Erica, the birth mother of Chandler and Monica’s future children. They meet Erica under false pretenses because the agency mixes up their profile with another couple.

They lie to her and pretend to be that couple, but eventually, they admit the truth. Chandler then convinces her to let them adopt her child. The Friends series finale finds Erica giving birth to not just one but two babies. They’re twins. The series ends with Monica and Chandler adopting two babies and moving out of Monica’s apartment, despite it being a steal with rent control. 

Monica and Chandler’s relationship has one of Friends' best arcs. They evolve from a great friendship to one of the best sitcom couples. Could they BE any more perfect for each other?