Friends remains one of the most iconic and timeless sitcoms ever, and every fan certainly has their favorite character. While this show is hilarious, it’s also actually pretty relatable. No character on this show is perfect, and in fact, many of them make quite a lot of mistakes throughout the series.

For Chandler fans, you know he’s likely to mess up his relationships, friendships, or his job, but that’s all part of being human. He has a heart of gold and certainly redeems himself, but they’re mistakes nonetheless. Of course, fans can learn from Mr. Bing. Here are 10 mistakes that Chandler made that viewers can actually learn from.

Everything With Janice

Janice is a recurring character in the series, and there are certainly fans that love this eccentric woman. Of course, every time Chandler dates her, sleeps with her, or even sees her, a mistake has been made.

We can learn from Chandler in this relationship, and how hard it can be to move on and be alone, rather than returning to what is familiar. Obviously, it’s best to leave the past in the past, and that’s one lesson we’ll always have thanks to these two.

His Shallowness in Dating

At the beginning of the second season, an entire episode is dedicated to how Chandler breaks up with women for petty reasons. In the same episode, “The One Where Heckles Dies”, Chandler realizes that he could be giving up something great, and that he might end up bitter and alone if he doesn’t change his mindset.

We’ve all been a bit petty and shallow, and Chandler shows us that we could be missing out on some amazing things with that attitude.

When He Makes Fun of Women

Fans all love the episode with guest star Julia Roberts. In this episode, “The One After the Superbowl”, Chandler meets up with his old schoolmate to have a date. However, it turns out that Chandler humiliated this woman in school, and while he’s busy seeking sex, she gets revenge on him.

If this teaches us anything, and makes us laugh, it’s that you should never tease women, especially when it comes to their sexuality. Of course, it’s also about not being obsessed with sex, and learning to accept your mistakes.

Rejecting Joey’s Thoughtful Gift

Some of Chandler’s least redeeming moments come from his friendship with Joey. They’re best buds, but Chandler can kind of forget about Joey’s feelings sometimes. When Joey buys Chandler a golden, engraved friendship bracelet, Chandler only notices how hideous and tacky it is. While he learns his lesson by the end of the episode, we can all learn from his mistake, too. It’s about friendship and the thought, not about money or looks.

Forgetting Which Sister

This is definitely one mistake that he’ll never live down. Fans will remember when Chandler drunkenly fooled around with one of Joey’s sisters, is invited to their family dinner, and then can’t remember which sister is the one he’s supposed to be dating.

The basic lesson here is to not date or hook up with your friend’s sister, but the bigger lesson is to be more cautious about your decisions, and that these kind of situations can be pretty hurtful. Not cool, Chandler. We’re sure he learned that women deserve more than this kind of drunken escapade.

When He Kisses Kathy

This is one mistake that certainly crosses all kinds of bro codes and friendship laws. When Joey is dating Kathy, Chandler can’t help but fall for her, and they end sharing a kiss. Of course, this ends up with Chandler in a box, which is hilarious, but it teaches us a really important lesson about friendship.

Chandler proves that friendship is what really matters, and that Joey deserves his loyalty. He went about this situation the worst way possible, and we can all learn from this train-wreck of a mistake.

His & Monica’s Secret

Monica and Chandler’s behavior during the initial stages of their relationships could definitely be viewed as a mistake. Chandler hides from his life-long best friend that he is seeing his sister. Sure, Monica is also hiding this information from her brother, so both of them are in quite the pickle.

After Ross finds out and supports them, it becomes clear they had nothing to worry about. Friendship doesn’t need secrets, and Chandler (and fans) can learn from this mistake, and that support and honesty is the best policy.

When He Doesn’t Believe in Joey

Fans will remember in the fifth season, where Joey lands a role in a movie in Vegas, that Chandler secretly doesn’t believe this will be Joey’s big break. Furious at his lack of support, Joey makes Chandler leave. Chandler learns that supporting your friends is the only thing you can do, and that negativity has no place in a good friendship. We can all learn from this, too, and that being there for your friends is the best thing one can do.

When He Almost Doesn’t Get Married

At the end of the 7th season, things get pretty sticky when Chandler gets cold feet and tries to flee his wedding. Of course, the boys rein him back in, and he realizes that he wants to spend the rest of his life with Monica.

This could have been way worse of a mistake, but we can all learn from this decision that love is scary, and having fear of marriage is totally normal. However, at the end of the day, being with your person is what matters the most.

Everything with Tulsa

When Chandler falls asleep in his meeting and ends up working in Tulsa, lots of sticky situations occur. Mainly, when he ends up working on Christmas Eve because of his position at his job. Honestly, most of Chandler’s mistakes end up with him resolving them in an incredible way, and this one is no different.

Chandler sends his employees home, but then he ends up quitting. He flies home to Monica and the gang, and realizes that his family is more important than any job out there. In fact, this even leads to him having a job he loves. We can all learn from this sequence of events, even if it started with a huge mistake.