Cookies help us deliver our Services. By using our Services, you agree to our use of cookies. Learn More.

Chandler And Monica's Best Friends Moments Ranked

When NBC's hit series "Friends" premiered in 1994, much of the pilot focused on the potential between Ross Gellar (David Schwimmer) and Rachel Greene (Jennifer Aniston). Sure enough, Ross and Rachel's on-again, off-again romance was a staple throughout the series' ten-year run. 

But late in Season 4, two of the other friends hooked up, and eventually became a stronger relationship backbone for the rest of the series. When Chandler Bing (Matthew Perry) and Monica Gellar (Courtney Cox) hopped into bed together, they became the real it couple of the series.

As the series' executive producer Scott Silveri told Vulture in 2019, Cox and Perry's chemistry inspired the writers to pair them up way back in Season 2. "There was a real, fun dynamic between the two of them," Silveri said. "Even as early as that, they said, 'Oh, they're kind of special together. If we're ever looking for another relationship, that's something to file away.'"

Thank goodness they did, because Chandler and Monica provided some of the sweetest, most adorable, and totally swoon-worthy moments of the entire show. With that in mind, here are Chandler and Monica's best "Friends" moments, ranked.

14. The one where Monica was high maintenance

Sure, isn't Monica a little high maintenance in every episode? But in "The One With The Joke" (Season 6, Episode 12), Phoebe insulted Monica by calling her high maintenance, claiming that Rachel would be a better woman to date because she was so easy going.

Being called high maintenance actually hurt Monica's feelings, and though she and Chandler were way into their relationship at this point, he still knew exactly what to say to help her out of her funk. 

Giving Phoebe and Rachel a lame, prepared speech, when he was finished he turned to Monica and said: "You're not easy-going, but you're passionate, and that's good. And when you get upset about the little things, I think that I'm pretty good about making you feel better about that. And that's good too. So, they can say that you're high maintenance, but it's okay, because I like ... maintaining you." 

This was also a call back to a Season 3 episode where Monica's "high maintenance" label came into play. That adorable moment, however, is higher up on this list.

13. The One where Chandler asked Monica to marry him ... the first time

The episode where Monica and Chandler actually got engaged will certainly be somewhere on this list, but the episode where Chandler proposes to Monica for the first time was "The One With The Birth" (Season 1, Episode 23). 

Ross' ex-wife Carol was giving birth to their son Ben, while quarreling with Carol's partner Susan. The rest of the gang were stuck in the waiting room, and as Monica watched some moms-to-be go in and out of the delivery room holding their little babies, she got a serious case of baby fever. Seeing a mom roll out with twins, she wondered why some women got two babies, while she had none.

That's when Chandler popped the question: He proposes that if neither of them are married by 40, they could get together and have some kids. While the sentiment was sweet, however, Monica took it the wrong way, asking: "Why won't I be married when I'm 40?!" 

Chandler's cute gesture was the first time a romance was hinted at between them. Who could have guessed that Chandler and Monica would indeed be married to each other by the time they were 40?

12. The one with the swing kings and the wedding dress

In "The One With The Cheap Wedding Dress" (Season 7, Episode 17), Monica and Chandler were in the process of planning their wedding when she, Rachel, and Phoebe headed to a discount wedding dress warehouse in Brooklyn. 

Monica found her perfect dress, but another woman wanted it in the same size, and they only had one at the store. After a confrontation, Monica nabbed the dress – but in retaliation, the woman booked the band that Chandler had his heart set on having play at their wedding: The Swing Kings.

The other woman ultimately agreed to swap the dress for the band. Monica tried to talk Chandler out of wanting The Swing Kings, but didn't reveal the part about the dress. But in learning more about Chandler's desire for The Swing Kings, he ended up saying something super sweet. As it turned out, the two of them had gone to a Swing Kings concert together early in their relationship and Chandler told the gang, "While Monica and I were dancing to them ... it was the first time I knew that you were the woman I wanted to dance all my dances with." Needless to say, Monica got a new dress.

11. The one with the flashback

In "The One With The Flashback" (Season 3, Episode 6), Monica was sad because Phoebe moved out — but it wasn't just that Phoebe moved out, it's why Phoebe moved out. The laid back flower child couldn't take any more of Monica's obsessive cleanliness and general high maintenance personality so, while sulking in a really fluffy towel, Chandler came in looking for some beers and asked her what's up.

Monica's sadness was really palpable in this scene, and watching it you can't help but feel horrible for her. Imagine one of your best friends moving out just because of the way you are. 

In her vent, she asked Chandler, "Am I so hard to live with? Is this why I don't have a boyfriend?" But Chandler was having none of it, telling her he had no idea why and that she should have a boyfriend. Giving her a huge hug, he says: "You are one of my favorite people. And the most beautiful woman I've ever known in real life." 

Of course, their lengthy embrace got a bit suggestive before being cut off by typical "Friends" humor. But the hints of Monica and Chandler's affections were there.

10. The one where Chandler peed on Monica

In the premiere of Season 4, the gang was still at a sand-flooded beach house while Phoebe stalked her birth mom. With Ross absorbed in deciding whether or not to get back together with Rachel and dump the bald Bonnie, Chandler, Monica, and Joey were having a relaxing time. 

In the Season 3 finale, Chandler and Monica began a fun flirtation where Chandler tried to convince Monica that he'd be a great boyfriend, presenting alternate scenarios in which Monica might go out with him. Their fun back-and-forth showed that even earlier in the series, Chandler and Monica were always kind of thinking about getting together, which is pretty cute.

Their flirty banter came to a crashing halt, however, when Monica was stung by a jellyfish while on the beach. 

In so much pain that the trio had to resort to something they saw on The Discovery Channel, they decide to employ urine as an antidote. Joey stepped up first, but failed to "peeform," so Chandler was needed to tackle the job. 

Of course, the pee incident killed the mood, but Chandler nonetheless tried to flirt one more time at the end of the episode, prompting Monica to tell him: "You'll always be the guy that peed on me."

9. The one where Chandler said I love you

In Season 5's Thanksgiving episode titled, "The One with All The Thanksgivings," the gang was rehashing tales of their worst Thanksgivings ever. 

With Ross going through a second divorce, he was firm that this was his worst; Phoebe referred back to her past lives losing limbs on battlefields; Chandler chose the Thanksgiving where his parents announced their divorce; Rachel smugly said she knew what Monica's was.

That's when the episode flashed back to Thanksgiving 1987, when Chandler came home with Ross for the first time. After meeting Monica, Chandler called her fat behind her back, inspiring Monica to lose a lot of weight.

But really, her worst was the following Thanksgiving. While trying to seduce Chandler with her new body, she dropped a knife on his foot, causing him to lose a toe. When Chandler stormed off in anger, Monica tried to cheer him up by putting a giant turkey on her head. The goofy scene caused Chandler to burst out laughing, saying "You're so great, I love you." 

Chandler tried to backtrack but Monica, still with a turkey on her head, knew he meant it. It's a sweet, silly, totally Monica and Chandler way to say that first I love you.

8. The one where they ended up together in an alternate reality

In the two-parter "The One That Could Have Been" (Season 6, Episodes 15 and 16), the friends pondered what their lives would have been like if they had made different decisions or chosen other paths in life. The possibilities are intriguing, to say the least.

Rachel imagined how her life would be if she married Barry; Phoebe imagined an alternate life as a Wall Street stockbroker; Ross imagined what life would be like if he was still married to Carol; Joey saw himself as a huge soap opera star. Monica, meanwhile, pondered what life would be like if she hadn't lost all that weight, asserting that Chandler (who envisioned himself as a struggling writer) would never have dated her.

But in a sweet, however convoluted way, Monica and Chandler still ended up getting together in this alternate reality fantasy. 

With Monica a 30-year-old virgin who kept getting blown off by boyfriend Roger, she and Chandler flirted like their usual selves, falling into bed together and starting a "friends with benefits" relationship. It's Chandler, however, that started having real feelings for Monica, and the adorable moment that Monica realized Chandler was the one who called in a fake emergency to her doctor boyfriend was where these two clicked in this alternate universe.

7. The one where they hooked up in London

The finale of Season 4, "The One With Ross' Wedding," was a two parter focused on Ross and Emily's London wedding. 

In the first half, Rachel hadn't shown up just yet, and Monica was still down about her own relationship prospects considering this was her brother's second marriage. So, when a drunken guest at the rehearsal dinner mistook Monica for Ross's mother, she got really depressed and drunk, and she and Chandler ended up sleeping together.

But their suspected one night stand in London was what kicked off their whole relationship. They spent the entire second half of the finale trying to find a way to bonk again, and kept getting foiled. The anticipation, attraction, and delayed gratification probably made these two yearn for each other even worse, and once their feelings started to form, Monica and Chandler's romance became the most genuine on the series.

6. The one where Phoebe and Chandler played chicken

Naturally, right after getting together in London, Monica and Chandler decided to keep their relationship a secret. 

At first it made sense. If they were just sleeping together, why complicate things by getting the friends involved? But as we now know, Monica and Chandler did fall in love, and even though Chandler said those three big words back when Monica had a turkey on her head, they still kept it from everyone. That is, until Joey figured it out. Then Rachel. Then Phoebe. This happened in the appropriately-named  "The One Where Everybody Finds Out" (Season 5 Episode 14).

The trio's knowledge of Monica and Chandler's sexual relationship set up a challenge. Phoebe started hitting on Chandler, then she asked him out on a date, which wasn't really a date, just a night in the sack. Chandler played along, but only at the behest of Monica whom, as we know, absolutely hates to lose. So, on the night of Chandler and Phoebe's date, they had some wine, Phoebe showed off her bra and did a little dance, and they went in for a kiss. 

It was Chandler that pulled away after an awkward embrace, and when Phoebe demanded to know why, Chandler explained: "Because I'm in love with Monica!" Chandler and Monica then declared their love for one another in front of three of their best friends, finally letting the cat out of the bag and being honest about their true feelings. Now, they only had to tell Ross. 

5. The one with the hard 8

Once Ross found out about his best friend and his sister being in love, he was totally fine with it. Which left Monica and Chandler to grow their relationship over the course of Season 5, with some ups and downs along the way. 

At the end of Season 5, they were having one of those downs. Joey was in Las Vegas, shooting a movie, when the gang decided to join him on a fun trip. On the plane, Monica revealed she innocently had lunch with ex-boyfriend Richard, which sent Chandler into a jealousy spiral. He told her she couldn't see Richard ever again, a demand Monica didn't take too well.

The duo spent most of the trip fighting and not talking to each other, and when Monica got sucked into gambling, Chandler threatened to leave, but Monica told him he's the love of her life and promised not to see Richard. 

The two started gambling together, hitting it big. On a major craps roll, Chandler blurted out that if Monica rolled a hard 8, they should get married that night in Vegas. Monica rolled the dice, and they flew off the table into a weird position. Monica told Chandler to make the call, and he said "It's a four," solidifying their hard 8 roll, essentially asking Monica to marry him right then and there. But we all know how their attempts ended, with a drunken Ross and Rachel getting married instead.

4. The one where they meet Erica

In the final season of "Friends," Monica and Chandler had struggled to have a baby and ended up choosing to go the adoption route instead. During the application process, they met a pregnant woman named Erica (Anna Faris), who was looking for new parents for her coming baby. But during their meeting, Monica and Chandler realized that Erica chose them because she got the wrong file and thought Monica and Chandler were a reverend and a doctor. The two come clean, leaving Erica disgusted that they didn't more immediately tell her the truth.

Chandler then jumped into action, and when he goes into serious mode you know he's not kidding around. 

He approached Erica by himself, saying: "My wife's an incredible woman. She is loving, devoted, and caring ... I love my wife more than anything in this world. And it kills me that I can't give her a baby." He then confessed that when their day finally came, he'd be ready to be a father, but Monica was already there: "She's a mother." 

Chandler's honesty moved Erica into choosing them, and had millions of viewers undoubtedly reaching for the Kleenex.

3. The one where they got married

Season 7 closed with Monica and Chandler's gorgeous, fancy wedding. But Chandler started getting cold feet and disappeared for a bit. 

When the guys finally tracked him down at his office, he said he was worried about ending up just like his parents: divorced and miserable. They talked him back into getting ready, just in time for another crisis to hit: Chandler overheard Phoebe and Rachel talking about how Monica was pregnant, running off again. But this time, Chandler simply ran down to the gift shop to buy some cigarettes and an adorable little NY baby onesie.

Monica and Chandler's wedding ended up being lovely and heartwarming, and the whole ceremony was filled with adorable moments that defined these two as a couple. But the sweetest moment came when Chandler told Monica he knew about the pregnancy, giving the most adorable hint of a smile that he was excited to be a daddy. But we all knew who was really pregnant.

2. The one where they became parents

The series finale of "Friends" was an emotional roller coaster episode for any fan of the show. Phoebe had married Mike a few episodes back, Joey was getting ready to make the move to Los Angeles for his spinoff "Joey," so the finale was mostly focused on Ross and Rachel getting back together and Monica and Chandler finally becoming parents.

But the duo was in for a surprise when Erica started delivering her baby and the doctor said: "The other one will be along shortly." 

Yup, Erica was having twins the whole time! Chandler's face upon hearing the news was typical Chandler shock, but it was Monica this time who put her foot down. Refusing to separate the two babies, she said they were both going home with her. Of course, Chandler got on board, but he was shocked. Watching these two lovable characters finally become parents was one of the series' best moments.

1. The one with their proposal

The absolute best Monica and Chandler moment in the entirety of "Friends" was their gorgeous, nail-biting proposal episode. 

In the finale of Season 6, Chandler planned on proposing to Monica but tried to throw her off, claiming he didn't want to get married. His plan backfired though, and Monica really thought he was not willing to commit, leading her to get back in touch with Richard. The gang  intervened, letting Monica in on the plot while helping her decorate the apartment with candles and surprising a stunned Chandler.

Monica got down on one knee to propose to Chandler, but kept bursting into tears and couldn't finish — so, Chandler popped down with her and they did it together. 

Through his tears, Chandler said: "You make me happier than I ever thought I could be. If you let me, I will spend the rest of my life trying to make you feel the same way." Monica and Chandler's proposal was their best moment, in a series filled with so many memorable ones.