Chandler Bing was the friend most likely to have a joke ready for any given situation. He prided himself on his sense of humor and considered himself to be the funniest of the group. However, while this was a large part of who he was, not all of his actions were as well-perceived as his jokes. Chandler had a habit of opening his mouth a bit too frequently when it was not called for, and occasionally let his fears and insecurities determine his decisions for him.
Chandler had his good moments and his bad moments just like any other person. Throughout ten seasons, it was inevitable that he would make his series of mistakes and bad choices. Here are the ten worst things that he's ever done.
10 Fell Asleep During Joey's Movie
After the many acting jobs in Joey's pursuit of a successful career, he was cast in a war film. Excited when the time comes for it to finally premiere, Joey is disappointed to learn that he only has one extra ticket instead of having enough for each of his friends. While Monica and Phoebe both ask Joey for a ticket, he decides to bring Chandler as a thank you for Chandler's support of his career.
Touched by the gesture, the two attend the premiere together. Unfortunately, Joey is only let down by his best friend when Chandler falls asleep during the movie. While Chandler apologizes for the actions later, he still hurt Joey's feelings.
9 Treatment of Janice
Janice was Chandler's on-again, off-again girlfriend for a while before he and Monica started dating. Chandler went from disliking her to falling for her to hating her all in a span of a few years. While Janice had a habit of being loud, outspoken, and unafraid to speak her mind, none of her actions were meant to be mean-spirited. She was genuinely happy to see Chandler and the rest of the gang whenever they would cross paths.
However, when Chandler was in the mindset of disliking Janice, he was often mean to her. To avoid a reconciliation with her, he lied about moving to Yemen. While he may have found her annoying, she did not deserve the way that he treated her.
8 Ignored His Father
Chandler had made it clear he did not have a close or easy relationship with either of his parents. When Monica finds out that Chandler did not invite his father to their wedding, she insists they go to and invite Chandler's father in person. Chandler also admits that – when they were both in New York – his father would reach out to him wanting to get together but Chandler would come up with an excuse not to.
He attempts to justify it by saying that his father had embarrassed him growing up by attending his school functions dressed up. Monica reminds him that his father was always there though, and that is the part that matters.
7 Told Monica She Could Not Talk To Richard
Near the first anniversary of Monica and Chandler's relationship, Monica has lunch with Richard and confides in Phoebe that she felt nothing for her ex-boyfriend anymore. Even so, she does not plan on mentioning it to Chandler for the risk of making him upset. When Phoebe accidentally reveals it, Chandler reacts above what Monica had anticipated.
While she knew he would be upset, Monica is surprised when Chandler, out of jealousy, declares that she can no longer speak to Richard at all. While speaking to an ex may have made Chandler uncomfortable, especially knowing the history, it is unacceptable of him to tell Monica who she can and cannot talk to.
6 Lost Baby Ben On A Bus
When Ross' son was born, it was no surprise that Chandler and Joey would babysit Ben. While they never needed to be perfect babysitters, the one thing that was expected of them was that they would not lose the baby. Quickly after realizing their mistake, Chandler and Joey track down where Ben would have ended up only to be shown two babies.
As neither Chandler or Joey remembered what Ben was wearing, it comes down to a guess. Luckily, they pick the right baby and the choice is confirmed after Ben cries when Monica holds him.
5 Slept With Joey's Sister
When Chandler gets drunk at a party, it leads to a choice that lands him in a lot of trouble: sleeping with Joey's sister. While having a one night stand with his best friends' sister was already a big problem, that is not the only one Chandler faces. The morning after, Chandler cannot remember which one of Joey's sisters he was with.
While having a meal with Joey and his family, Chandler tries to make amends only to realize that they all look too similar to him to tell which sister is which. This is especially clear when he is encircled by all of Joey's sisters and Joey himself.
4 Kisses Joey's Girlfriend
Chandler had a few relationships, but often had a difficult time truly connecting with anyone. This is one of the reasons Kathy is so important to him. He feels something real for her but there is one drawback – by the time he meets her, Joey has already asked her out. Frustrated but not willing to backstab his best friend, Chandler suffers, ranting to his friends when Joey is not around and desperately trying not to let his real feelings show.
As much as he tries, his feelings for Kathy are mutual and they act on them when Joey isn't there. When Joey finds out, he makes Chandler sit in a box as revenge, but eventually forgives him.
3 Called Monica Fat
It has been proven throughout the series that Chandler tends to speak his mind too much, making jokes when he should not and failing to filter his statements. While visiting the Gellar family during Thanksgiving for the first time, Chandler shows discomfort about being near Monica due to her size and tells Ross that he does not want to spend time with his "fat sister."
Chandler claims that this statement should not have mattered because he said it behind her back, but his comment changed Monica's opinion of herself and made her feel that she needed to lose weight. In response at the following Thanksgiving, Monica's attempt at revenge goes south and ends with Chandler losing a part of his toe.
2 Runs Before His Wedding
After years of being scared of commitment, Chandler matured while being with Monica and decided to marry her. His fear of committing was always a part of his inability to stay in a relationship and – when it seems as if Chandler will be able to confidently walk into his wedding – an outgoing voicemail referring to he and Monica as "the Bings" is enough to set him over the edge.
Terrified at the prospect of "the Bings," Chandler runs and leaves a note behind as an apology to Monica. It takes Phoebe and Ross to find him and talk his fears down, taking him one step at a time to reach the ceremony while Rachel stalls Monica until Chandler is found.
1 Announcing Ross' Death
When a student-alumni webpage goes up, Ross is interested in the prospect of his profile. After Chandler and Joey post on his page as a joke, Chandler and Ross end up in a prank battle on the website to make each other's reputations worse.
Chandler takes the joke too far when he decides to tell everyone that Ross has died in a blimp accident. Ross (hiding in a bedroom), Monica, and Chandler host a fake service to see how many people show up, only for one person to appear for Ross. While Chandler was trying to make a joke, he does it by making a serious claim that would worry Ross' parents and mess with other people's feelings.