Top 10 Most Embarrassing Things That Happened to Chandler on Friends

Chandler’s issues with his father are well-known, but it seems like he just doesn’t have luck with father figures in general. After Monica asks Chandler to bond with his soon-to-be father-in-law, things spiral out of his control. While he’s initially successful in making Jack like him, even being allowed to call him “dad”, Chandler ends up getting too close for comfort. When he forgets to take off his new glasses in the steam room, a momentarily blinded Chandler scrambles for a seat, only to realize he’s landed on Jack’s lap. Horrified and embarrassed, he has to endure his friends’ humiliating remarks of “bonding” with his father-in-law. Unfortunately, his embarrassment doubles by the end when he shows way more of himself to Jack than he ever wanted.

In his younger days, Chandler went through a long period alone in search of love. One of his earlier potential romances was with Jill Goodacre, a gorgeous model clearly out of his league. Upon being trapped with Jill in an ATM vestibule during a blackout, Chandler endlessly debates in his mind how to approach her. After some prodding from Joey over the phone, he decides to play it cool, but only manages to make Jill uncomfortable through his awkward wordplay. Accidentally spitting out the stick of gum Jill offered him, Chandler ends up choking when he realizes he’s put back someone else’s gum in his mouth. Although he pretends everything’s fine at first, he almost passes out before Jill comes to his rescue.

After Monica convinces Chandler to take a bath, he starts to fall in love with it - but finds himself unable to successfully draw them as well as she does. So, he ends up ‘stealing’ a bath that Monica drew for herself. Before she can exit the bathroom though, Phoebe barges in, followed by Joey himself, then Rachel and of course Ross to complete things full circle. Meanwhile, Chandler’s bubbles are slowly and inadvertently showing more of himself than he’d like, causing the friends to comment and Monica telling him to cover up with a toy boat. It ends with Ross and Rachel revealing the sex of their baby, resulting in hugs all around, while Chandler awkwardly says, “I’ll get you later!”

Known for his childish antics and fun loving personality, Chandler wasn’t considered a suitable parental figure by his friends until the end of the series. He’s seen at his most juvenile when he helps to take care of Phoebe's nieces and nephew. After he doesn’t exactly have the time of his life changing the babies’ diapers, Chandler tries to make playtime more fun by bringing over an unsuitable toy figure. However, in his attempt to prove the toy’s safety, he accidentally swallows its gun. After spending the rest of the episode struggling to breathe with the gun lodged in his throat, Chandler then has to be taken to the emergency room. By the end, his recurring commitment issues ensure another meltdown.

It seems as if fate’s decided to smile on Chandler when he receives a call on his answering machine from a seductive woman named Jade. In order to have a chance with her, Chandler pretends to be Bob, the person Jade meant to call, and arranges a date at the coffee shop. Swooping in as a kind and trustful stranger with a heart of gold, Chandler manages to win Jade over, making her believe Bob’s abandoned her. Unfortunately, after he brags to Ross about hooking up with Jade, he receives another call from her. Still believing it to be Bob’s number, Jade shares Chandler’s unsatisfactory performance in excruciating detail. Speechless, he painfully learns the exact reason why Jade found the experience so awkward.

After wrestling with his feelings for Joey’s girlfriend Kathy for a long time, Chandler crosses the line when he and Kathy kiss, prompting her to break up with Joey. Facing no other option to earn an enraged Joey’s forgiveness, Chandler is forced to lie in a box for hours in order to prove his loyalty. This was in response to the time when Joey had been locked in a TV cabinet during a robbery. While the other friends gather for Thanksgiving dinner, Chandler is left trapped in the box, and when he angers Joey for not taking things seriously, he’s forced to stay completely silent. The worst part is when Kathy arrives to say goodbye, and all Chandler can do is sadly finger wave her away.

When Monica finds out Chandler shared her secret with Phoebe, she gets back at him by revealing one of his greatest insecurities. Now outed for having a third nipple, Chandler is pestered by his friends for the remainder of the episode to share more details about it. And while he tries to deflect his embarrassment with his usual blend of sarcastic remarks, Ross still manages to come up with creative jokes at his expense. His unusual anatomy truly comes to haunt him in his romance with Ginger, who, upon discovering his “nubbin,” quickly finds a reason to end their relationship. Maybe this was karma for all the times Chandler had broken up with girls for superficial reasons.

No matter how many times Chandler tries to convince his friends he can keep a secret, his actions tell us otherwise. In this episode, Phoebe sets Monica and Chandler up to meet her friends Bill and Colleen to learn about the adoption process, which spirals into disaster. When Chandler meets young Owen, he leaves the child horrified by accidentally revealing that he’s adopted. Not knowing how to deal with the situation, he attempts to bribe Owen to secrecy, but is busted in front of Bill and Colleen. To make matters much worse, Chandler’s blithering attempts to apologize result in a traumatized Owen learning the truth about Santa Claus, and he and Monica have no choice but to escape.

Whether it’s fighting over cheesecakes or sharing awkward moments, Rachel and Chandler stories always steer out of control. So, it’s no surprise Chandler’s romance with Rachel’s boss Joanna came back to haunt him. After attempting to break up with Joanna upon Rachel’s urging, Chandler is instead seduced in her office. Unfortunately, he’s left handcuffed to a chair for hours when Joanna leaves for a meeting. An angered Rachel refuses to help Chandler upon discovering him. With nowhere to go, Chandler begs her to set him free, but ends up in a scuffle over his pants. When all his attempts to convince Rachel fail, he’s forced to make a deal with her to stay, which doesn’t last long as Joey exposes his lies.

Before we unveil our top pick, here are a few more embarrassing mentions.

Getting Stuck with a Crazy Roommate
“The One Where Eddie Won’t Go”

Pretending to Seduce Phoebe & Failing at It

Showing Off His Awful Dancing Skills
“The One with All the Wedding Dresses”

Being an Old Intern
“The One with the Mugging”

Being Forced to Go to Yemen to Avoid Janice
“The One with All the Rugby”

Talk about a blast from the past: Chandler’s past hit him right in the face. When he runs into Susie Moss, his former classmate from elementary school, he’s pleasantly surprised to learn she’s interested in him. After they begin dating, Susie presses him on to be more adventurous and propositions him in a bathroom stall during dinner. To Chandler’s horror, though, she steals his clothes and reveals her true intentions. Having concocted an elaborate plan to get back at Chandler for humiliating her in school, she leaves him stranded - and wearing only her panties - to feel a similar shame. When Ross and Joey’s arrival only brings in further jokes at his expense, a desperate Chandler has no choice but to step out in public in all his glory.