3 times Chandler embarrassed himself in Friends (& 3 times he outshone others)

Chandler Bing, the hilarious and sarcastic buddy from Friends, had plenty of awkward moments during the show's 10 seasons. But there were also some great moments where his witty jokes and emotional intelligence shone brighter than the rest of the group.

Sadly, Matthew Perry, the actor who skyrocketed to fame as Chandler Bing, passed away in 2023 at the age of 54.

Fans continue to love Chandler, and all the hilarious and heartwarming moments he brought to Friends. From his adoption slip-ups to his extra nipple, Chandler never failed to make us laugh. Not to be forgotten is how he was there for Ross during tough times and finally admitted his feelings for Monica.

Chandler was able to handle tricky situations, like his banter with a gorgeous model, showing that he was more than a socially awkward person. Perry's comedic timing and talent for adding sarcasm to any chat made Chandler a fan favorite on Friends. In this article, we'll check out three moments when Chandler made a fool of himself and three times when he nailed it.

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Chandler Bing's top 3 most embarrassing moments on Friends

1) Accidentally revealing a child's adoption (The One Where Ross Is Fine, Season 10, episode 4)

Chandler's awkwardness and lack of discretion caused a major embarrassment for him on Friends. During a meet-up with Phoebe's friends, Bill and Colleen, to discuss adoption, Chandler accidentally reveals to a young boy named Owen that he was adopted.

This upset Owen, and Chandler's attempts to make it right only made things worse when he also spilled the truth about Santa Claus. The whole situation was a cringe-worthy display of Chandler's knack for saying the wrong thing at the wrong moment.

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2) Engaging in a fake flirtation with Phoebe (The One Where Everybody Finds Out, Season 5, episode 14)

Chandler ended up in a pretty awkward situation when he had to pretend to flirt with Phoebe to hide his relationship with Monica. Throughout this Friends episode, he struggled through the fake dates and uncomfortable moments until it all became too overwhelming.

To make matters worse, the rest of the gang already knew about Chandler and Monica, adding to the embarrassment as Chandler tried to keep up the facade.

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3) Revealing his third nipple (The One with Phoebe's Husband, Season 2, episode 6)

Chandler's quirky body feature caused him some awkward moments on Friends, especially when Monica spilled the beans about his third nipple to Phoebe. His pals wouldn't let him live it down, constantly teasing him and making jokes about his "nubbin."

Chandler tried to brush it off with his usual sarcasm, but it didn't work. His extra nipple even played a part in his breakup with Ginger, who used it as an excuse to end things with him.

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Chandler Bing's top 3 best moments on Friends

1) Declaring his love for Monica (The One Where Everybody Finds Out, Season 5, episode 14)

Chandler stepped up and showed his dedication to Monica in a big way in this episode. This was unexpected, as previously on the show, he had been willing to sacrifice his relationship with Kathy to keep his friendship with Joey intact.

When the gang found out about Chandler and Monica's secret relationship, Chandler didn't back down— he declared his love for Monica, proving he had grown as a person and was willing to prioritize his romantic relationship over his fears.

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2) Comforting Ross after his divorce (The One Where Chandler Can't Remember Which Sister, Season 6, episode 9)

In the episode where Ross was going through his divorce with Carol, Chandler showed his emotional intelligence and supportive side. He was there for Ross, giving him advice and being a good friend during a tough time.

It was great to see Chandler's caring and understanding side shine through, showing that he's more than just a funny, sarcastic guy. This moment highlighted how much Chandler has grown as a friend and how much he cares about the people in his life.

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3) Witty banter with Jill Goodacre (The One with the Metaphorical Tunnel, Season 2, episode 14)

Chandler showed off his fast humor and cool under pressure when he hung out with the stunning model Jill Goodacre. They got stuck in an ATM vestibule during a blackout, and Chandler cracked some hilarious jokes and kept the conversation going.

Even though he choked on his gum, Chandler's witty remarks and clever comebacks proved how much more he was than just a nervous guy. This episode highlighted Chandler's charm and charisma, which always managed to shine through despite his awkward moments.

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You can catch Friends, the iconic show that introduced us to Chandler Bing, on different streaming services like HBO Max and Netflix.