9 Times Chandler Bing Showed His Softer Side on 'Friends'

The hilariously sarcastic Chandler Bing is best known for his sarcasm and wit, but there were a ton of sweet moments on Friends like these where he showed his softer side.

Amber Garrett - Author

Apr. 5 2019, Updated 12:39 p.m. ET

chandler bing sweet moments friends
Source: Warner Bros. Television

When you think about Chandler Bing on Friends, you probably think of funny one-liners delivered with a sarcastic tone that couldn't be any sharper. Yet over the course of 10 seasons, the "transponster" with a heart of gold really showed off a softer, sweet side that made us melt. From tender moments with Monica to his epic bromance with Joey, here are nine times Chandler surprised us by being sweet instead of salty. (Spoiler alert — a lot of them involve Monica.)

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The one when he tells Monica the life he imagines with her.

monica chandler moments
Source: Warner Bros Television

Season 7, Episode 2

For someone as afraid of commitment as Chandler, he really evolved when his friendship with Monica turned into the love of his life. Perhaps one of the sweetest reveals is when he tells Monica with such specific detail and quiet ease the kind of life he pictures with her: four kids and "a small place outside the city, where our kids could learn to ride their bikes and stuff." 

The scene gives us a double dose of sweet by showing he's even thought of what to do about his BFF. "Of course, we'd have an apartment over the garage where Joey could grow old."

The one when he lost at "Cups" to help Joey out.

chandler joey moments
Source: Warner Bros Television

Season 6, Episode 6

The only relationship that could possibly eclipse Chandler and Monica is Chandler and Joey, and the episode where Chandler moves out is a prime example. Worried about how Joey will make ends meet without him, he invents the game "Cups," ensuring he'll lose to Joey no matter what. The ruse helps him give his pal $1,500 to pay the bills while preserving his pride. Too bad Joey lost it all later to Ross when he tried to teach him how to play.

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The one when he explained why he loves the Swing Kings.

chandler swing kings
Source: Warner Bros Television

Season 7, Episode 17

The reason why Chandler was so insistent on the Swing Kings being their wedding band is just about the sweetest thing I've ever heard, especially because of how reluctant he was to say something so vulnerable. "Well, it's just that 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."

If that's not worth giving up your dream wedding dress, I don't know what is.

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The one when he tells Monica she's high maintenance...

monica high maintenance
Source: Warner Bros Television

Season 6, Episode 12

The trouble with a lot of high maintenance people is that they don't realize they're high maintenance. Monica is one of those people. Thankfully, she found the perfect partner, as evidenced by the impromptu speech he gives (after the prepared one she gave him).  

"I’m sorry. 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."

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The one when he and Monica find out they can't have kids.

the one with the fertility test
Source: Warner Bros Television

Season 9, Episode 21

Nobody was more born to be a mom than Monica, so when Chandler had to deliver the results of their fertility test, it definitely broke us. But it also gave Chandler the opportunity to be the emotional rock, telling her, "we're gonna figure this out."

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The one where he cries about Ross and Rachel.

the one where chandler cant cry
Source: Warner Bros Television

Season 6, Episode 14

Even though it's played for laughs, it's very sweet how much Chandler ships Ross and Rachel, to the point where, despite everyone's failed attempts to make him cry, the thing that broke him was those crazy kids being unable to work it out. It's sweet to watch his cynical exterior crumble to reveal his secret romantic side.

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The one where he talks about what a great mother Monica will be.

the one with the birth mother
Source: Warner Bros Television

Season 10, Episode 9 

The way Chandler makes himself vulnerable to convince Erica to choose him and Monica to be her baby's parents is one of the most emotional moments in the show, and it shows not hust how tenderly Chandler feels toward her, but how much he truly sees her: 

"My wife's an incredible woman. She's loving and devoted and caring. And don't tell her I said this, but the woman's always right. I love my wife more than anything in this world. And it kills me that I can't give her a baby... I really want a kid. And when that day finally comes, I'll learn how to be a good dad. But my wife... she's already there. She's a mother... without a baby... Please?"

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The one where Chandler and Monica get married.

chandler monica wedding
Source: Warner Bros Television

Season 6, Episode 25

"I thought this was going to be the most difficult thing I ever had to do. But when I saw you walking down that aisle, I realized how simple it was. I love you. Any surprises that come our way, it's OK because I will always love you. You are the person I was meant to spend the rest of my life with. You want to know if I'm sure?" 

Also, can we just talk about the string quartet rendition of "Everlong" by the Foo Fighters at the end of this wedding? What a brilliant and unexpected choice.

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The one when he and Monica propose to each other.

chandler monica proposal
Source: Warner Bros Television

Season 6, Episode 25

Guys, I can't even think about this scene without tearing up. Monica gets too emotional to follow through, which is expected, but what catches us out of left field is when Chandler, despite his trouble crying at pretty much anything, gets choked up as he tells her how he feels. 

"I thought that it mattered what I said or where I said it. Then I realized the only thing that matters is that you make me happier than I ever thought I could be. And if you’ll let me, I will spend the rest of my life trying to make you feel the same way."

BRB, grabbing tissues. 

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