Chandler Bing has often been a rather divisive character on Friends. Much like any other fallible human, Chandler isn’t perfect. He’s hurt some of his best friends and, on the other side of the coin, has been hurt by people he thought to be friends. Sure, he’s been given some of the best jokes in the series’ history, but sometimes, as Ross has once said it, his words hurt.
While Chandler is only human, he has made a few missteps in his life, missteps that have made the other friends call into question whether Chandler is being a good friend or kind of a jerk.
10 Felt Bad: Accidentally Telling Rachel That Ross is in Love With Her
Chandler and Ross met in college and have been friends ever since. From their Miami Vice days to performing in their band Way, No Way, the two gents have a bond that allows them to share everything with one another—including who they might be in love with or not.
In Season 1, while Ross was away in China on a dig, Chandler gives Rachel a rather sentimental gift from Ross, one that speaks volumes about Ross’ love and appreciation for her. While Rachel sees it as just an extremely thoughtful gift, Chandler, unfortunately, let’s slip that this type of gesture shows just how much he’s in love with Rachel. This news is a surprise to everyone, including Rachel, who didn’t have any idea that Ross felt this way.
9 Bad Guy: The One Where He Kissed Kathy
The Kathy situation is a divisive plot point for some fans. While some found this to be a less-than-stellar story thread for Chandler and Joey, others found it to be interesting and a test to the comedic duo’s friendship. When Joey meets Kathy (Paget Brewster) in acting class, he instantly finds her attractive and promptly starts dating her; however, before this reveal, Chandler sees her at the coffee house and finds her so striking, he works up the nerve to ask her out, only to find that his roommate has beaten him to it.
As the story arc progresses, the tension between Kathy and Chandler boils over and results in the two of them kissing behind Joey’s back. Plainly put, there is no justification for Chandler at this moment. He’s not only embarrassed, but has also hurt his best friend in the process.
8 Felt Bad: The One Where He Finds Out Janice Kissed Her Ex-Husband
Chandler and Janice, for the longest time, were looking to be the couple that would be on-again, off-again for years to come. When they worked as a couple, they worked nicely. When they didn’t work, it was a hilarious train wreck. When Chandler falls head-over-heels for her, he begins to think that maybe he’s ready to settle down and be a grown-up in a real grown-up relationship.
It’s not until Joey finds Janice kissing her ex-husband that all of Chandler’s hopes and dreams of being with Janice go flying out the window. It’s hard not to feel bad for him as he’s finally ready to take the plunge and fall in love with his whole heart, only to be hurt and regress into a terrible commitment phobia.
7 Bad Guy: The One Where He Wouldn’t Call Joanna
In Season 4, reeling from his relationship with Janice, Chandler is introduced to Rachel’s boss, Joanna (Alison La Placa). In his words, Joanna is a rather dull woman with a constant set of goop hanging out in the corner of her eye.
Now, any normal adult who realized they just weren’t the right fit for someone, would have the common decency to sit this person down and end the relationship. However, unable to be a normal human in a relationship, Chandler consistently offers to give her a call sometime. In his pea-brain, he believes this is sparing her hurt and heartache, but it only serves to make her anxious for the phone call that will never come.
6 Felt Bad: The One Where He Trips On The Jump Rope
Bullies are no fun, even when you are a 20-something adult. When Ross and Chandler become entangled with two bullies at the coffee shop, they go into hiding, afraid of what beat down they might suffer. However, they quickly realize that they are adults and they won’t be pushed around. When the bullies egg them into fighting in the streets, Ross and Chandler will stand up to their bullies. The fight is short-lived as thieves steal the bullies and Ross and Chandler’s things, which forces the adversaries to work together to get their stuff back.
That is, everyone but Chandler. While Ross and the bullies commenced in the fight, Chandler missed it all, having blacked out from tripping over a little girl’s jump rope. It’s hard not to feel bad, as Chandler, once again, was about ready to show some personal growth only to have it ripped away from him.
5 Bad Guy: The One Where He Makes Fun Of Monica’s Body
Over the years, fans have criticized Friends for how they portray Monica when she was in college. What’s worse is that her being overweight is often the butt of a lot of jokes, including from her future husband, Chandler.
During a Thanksgiving episode in Season 5, it’s revealed that back in college, while Ross and Chandler were visiting, Monica overheard Chandler calling her fat, which hurt her tremendously. It’s not a great look for Chandler as it makes him seem rather shallow and one of the bigger jerks of the series.
4 Felt Bad: The One Where He Proposes To Monica… To Resolve A Fight
After everyone found out about Monica and Chandler being an item, the gang begins to fantasize about what their future wedding might be like, offering ideas and jokes to the happy couple. However, being the damaged commitment-phobe that he is, Chandler begins to freak out and take it out on the woman that he loves. As expected, this does not go over well with her and the two get into a large fight about his inability to commit.
Knowing he’s messed up and that he needs to figure out how to resolve this one on his own, he figures out just how to say that he’s sorry to his girlfriend—he buys her an engagement ring. While proposing to a woman to say that you are sorry might be seen as a bad guy move, you can’t help but feel bad for him, this commitment-phobe is finally starting to grow up, even if it is a bit of a stumble out of the gate.
3 Bad Guy: The One Where He Can’t Remember Which Sister He Kissed
Having just broken up with Janice, Chandler is hurt and looking to do anything he can to forget her. The best way to accomplish this is with a dozen jello shots and a birthday party for his best friend Joey. The flaws in this plan become apparent very quickly, as it comes to light that Chandler drunkenly makes out with Joey’s sister. The even more messed up part is that he can’t remember which sister.
This is certainly not one of Chandler’s brightest moments as he is not only hurting his best friend, but he’s disrespecting Joey’s sister the most by playing with her emotions only so that he can feel better about himself.
2 Felt Bad: The One Where He Connects With Mr. Heckles
Mr. Heckles wasn’t always the nicest downstairs neighbor. He would often bang on the ceiling and come up to the girls’ apartment to complain about their constant noise. However, when he dies in the second episode of Season 2, Chandler realizes that he and the former neighbor share similar pasts.
This realization that Chandler is on a course to be a lonely recluse because he pushes away anyone who shows him the slightest bit of affection, scares him more than anything else he’s faced up to that point. You can’t help but feel bad for him, as he comes to terms with his biggest flaws and is given a glimpse of what his lonely future might be.
1 Bad Guy: The One Where He Pretends To Be Bob
When a woman named Jade mistakenly calls Chandler’s number looking to hook up with an old fling named Bob, Chandler jumps at the opportunity to sleep with her.
This may be the worst thing that Chandler has ever done. He makes Jade think Bob stood her up and preys on her.
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