Chandler may be the lovable, charming, permanently self-deprecating member of the Friends crew, but that doesn’t mean he doesn’t have his moments of selfishness! Over the years, Chandler has done some pretty awful things in the pursuit of women and his own self interest (usually both), and they show that he may like to crack jokes at his own expense, but he’s not shy when it comes to being shameless from time to time.
From inappropriate behavior in relationships (over and over again), to not respecting Monica’s boundaries and lying about his friends, these are some of the most utterly shameless things that Chandler Bing has ever done.
Used A Baby To Pick Up Women
Not just any random baby, thankfully, but baby Ben. Back in the second season, Chandler and Joey figured out that women find babies adorable, and decide to ‘babysit’ Ben in order to try and get a little female attention… and it works. Of course, it works a little too well, when Chandler and Joey then forget about Ben entirely and leave him on a bus. And just to make this particular entry a little more shameless, when they do go pick him up, they try to lie to Ross about it - and he only finds out because Ben’s diaper was changed, and had a ‘department of transportation’ label on it. Using a baby, losing a baby, and then lying to a friend? Shameless, Chandler.
Fell Asleep At Joey’s Premiere
For most of the show, Joey is struggling as an actor, and Chandler is there to support him. He pays rent, drives him to auditions, and keeps believing in him… but when Joey actually gets a big break (other than Days of Our Lives) and is in an actual movie, Chandler falls asleep at the premiere. Not only is this incredibly rude and insensitive, but it seems like Chandler didn’t even bother making sure he got a decent night’s sleep for the big premiere - what was more important? Thankfully, Joey is ready to forgive him when he realizes the financial value of Chandler’s support, but still.
Got Back Together With Janice (To Avoid Being Alone)
Chandler’s treatment of Janice in general is pretty darn awful, but this may be his most shameless moment with her. When the gang are having a New Year’s Eve party, they all agree not to bring dates, so that they would be equally dateless on the big night. However, everyone ends up inviting someone to avoid being alone when the ball drops, and for Chandler, that’s Janice. Of course, he doesn’t actually want to be with her, and then tells her that at the party - essentially dumping her at the party and making her cry on NYE. Of all his crappy behavior toward Janice, using her and then dumping her at a party has to be in the top three.
Told People Ross Was Gay
This goes back to Chandler’s college days, when he and Ross were both interested in the same girl. Instead of simply both asking her out, and seeing if she was interested in either of them (shocking concept), when she asks Chandler about Ross, he tells her that Ross is gay.
To make matters worse, he says that Ross is in a relationship with a third man, who was also interested in the woman, thus taking them both out of the running with a horrible lie. Chandler may have been young and stupid, but this was pretty shameless behavior.
Picked A Roommate To Get Laid
Joey wasn’t Chandler’s first choice in roommate… no, that was the guy who was a photographer, so would have lots of semi-naked models in the apartment. In a flashback, the series shows Chandler interviewing for roommates, and when he realizes that one option wants to have models around, and spends weekends at his porn-star sister’s beach house (where Chandler would be welcome to join them), Chandler leaps at the chance. It’s all so that he can perv on sexy women, which is a pretty shallow reason to pick a person to live with! Thankfully, Mr Heckles scares Eric (the photographer) off, and Joey could move in instead.
Pretended To Want A Relationship With Joey’s Sister
This whole situation was pretty appalling… and it just kept getting worse. At Joey’s birthday one year, Chandler is upset about yet another breakup with Janice, and gets blackout drunk. On its own, that’s pretty reasonable, but then he proceeds to make out with one of Joey’s sisters in his drunken state. Then, rather than just admitting to Joey that he was blackout and didn’t know what he was doing, he lies and claims that he wants to be with her. Of course, he can’t remember who she is, so he goes to Joey’s house and tries to fake it - and ends up kissing a different sister in the closet instead!
Claimed Ross Was Dead
Chandler’s concepts of practical jokes don’t always really land… there was the time he tricked Joey into drinking a glass of fat, the time he stole Joey’s underwear, and of course, the time he pretended Ross was dead. As part of a series of ‘pranks’ between the two of them that starts when Chandler writes ‘Ross has sex with dinosaurs’ on their alumni page.
Ross retaliates with claims that Chandler is gay, and so Chandler then ups the stakes by saying Ross is dead. Not only is this whole thing totally childish, but Chandler seemingly has no remorse about lying about his friend and convincing people that he passed away.
Broke Into Monica’s Private Closet
Monica and Chandler, for the most part, have a great relationship… but that doesn’t mean it’s perfect. For example, after Chandler moves in, he asks Monica why a closet is locked - and she tells him it’s private, and to please just leave it be. So what does Chandler do? Freaks out, and then breaks into it. He actually takes the entire door off its hinges, and then actually makes fun of Monica for what he finds there (that Monica is a little bit messy). Nothing like some healthy boundaries!
Slept With His Best Friend’s Sister At His Wedding
This one may have turned out well in the end, but there’s no getting away from the fact that sleeping with Ross’s sister at Ross’s wedding to Emily was a pretty impressively shameless thing to do. Even in this group, there are still some lines that shouldn’t be crossed, and not only did Chandler start sleeping with Monica at the wedding, but he lied about it, hid it from everyone, even kicked Joey out of their shared room to do it, and then forced other people to get in on the lie.
Stole Cheesecakes
Finally, something a little lighter… Chandler (and Rachel) became cheesecake thieves! When a cheesecake is incorrectly delivered to his apartment, Chandler actually opens it and starts eating it - a crime, as well as a totally appalling thing to do. And of course, when the replacement is delivered to the right apartment, the two actually steal it off her doorstep and run away with it. That had better be some truly delicious cheesecake… especially as Chandler could easily have afforded to just order his own.
