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10 Times Chandler Found Himself In A Sticky Situation In Friends

Fans of Friends know Chandler Bing best for his social awkwardness, often masked with humor. He consistently faces ongoing challenges in his dating life and attempts to overcome his fear of commitment. Chandler notably also has a repetitive struggle to find a suitable career path, even though he is financially one of the most stable of the gang.

RELATED: 10 Life Lessons We Learned From Chandler Bing In Friends

Chandler's sticky situations have most certainly defined and shaped his character in the long term and taught him some valuable lessons in life. While other situations are simply silly mistakes that make fans laugh and shape some fantastically brilliant one-time episodes.

10 Escape To Yemen

The episode "The One With All The Rugby," sees Chandler re-ignite his relationship with old flame Janice after a chance meeting. Realizing that he doesn't wish to pursue the relationship yet again, Chandler invents a tall tale in the hopes that it will make Janice leave him alone. Chandler leads Janice to believe that he is moving to Yemen and never returning. His plan backfires and Chandler is forced to actually buy a plane ticket to board a plane to Yemen.

RELATED: 10 Reasons Chandler & Janice Were Doomed From The Start On Friends

While Chandler goes to extreme lengths to escape on this occasion, he is happily back home in the next episode and the situation is apparently resolved with no real explanation. Chandler's scheming to get out of bad dates or situations is all too familiar for his character. Throughout the early seasons of the show, Chandler has a known fear of commitment and is always trying to come up with a plan to get himself out of another mess.

9 New Job In Tulsa

Chandler makes a huge mistake during a work meeting, during the episode "The One Where Emma Cries." Chandler accidentally falls asleep during a meeting and upon waking up, he is confused to discover that his boss now believes that he has agreed to move to Tulsa for work.

This seemingly simple accident has a major impact on the plot point. His move to Tulsa puts a strain on his life and relationship and it all becomes too much - which ends with him dramatically quitting and coming home. The string of events is a blessing in disguise and leads to Chandler’s eventual dream job in advertising.

8 Baby On The Bus

Chandler isn't always alone whilst getting into sticky situations and this particular moment in time is one of Chandler and Joey's biggest joint accidents. The episode "The One With The Baby On The Bus," sees Ben left in the care of Joey and Chandler. Things don't go to plan when the friends are distracted by potential dates and Ben is accidentally left on the public bus.

This is the first time viewers Chandler interacting with kid's in the show and while this is an amusing one-off episode, it certainly is a wonderful contrast to see how Chandler develops through the seasons, ultimately becoming a father himself in the show's final season.

7 The Late Bachelor Party

Chandler discovers that Monica had a secret Bachelorette party before their wedding. Monica convinces Chandler to have a late, post-wedding bachelor party to make up for it. The episode "The One With The Stripper," centers around the guys finally throwing a bachelor party for Chandler, and much to his surprise, Monica hires a stripper for the occasion. Things soon take a messy turn when it is evident that Monica accidentally hired a prostitute instead of a stripper.

RELATED: 5 Times Joey Was Chandler's Best Friend (& 5 It Was Ross) On Friends

This episode truly displays the trust and love held between Monica and Chandler, making them one of the most secure and relatable couples on the show. It also re-visits the fans' love for the friendship duo of Joey and Chandler together, Joey even comments that he has missed being able to spend time with his best friend and typically getting into hilarious situations together.

6 Handcuffed In The Office

Having previously dated Rachel's boss, Joanna, Chandler always found her to be boring and things never worked out between them. The episode "The One With The Cuffs," sees Chandler rekindling things with Joanna, much to Rachel's annoyance and disapproval. Things take a quick turn when Rachel later finds Chandler handcuffed in a compromising position in Joanna's office.

This is one of Chandler's many terrible dating situations prior to Monica and another great example of how Chandler runs from anything serious. This episode also takes a closer look at Chandler and Rachel's friendship which isn't typically looked at too often during the show's run. Chandler proves in this episode that when he is feeling down about his life, he can often be a pretty poor friend.

5 Forgetting Joey's Sister

The episode "The One Where Chandler Can't Remember Which Sister," sees Chandler drinking way too much at Joey's birthday party. Chandler confesses to his friends that he kissed one of Joey's sisters at the party and the worst part is, he can't remember which sister.

Chandler classically digs himself into a deeper and trickier situation through this episode, as he tries to avoid the wrath of big brother Joey. Knowing that he has overstepped into the family territory, Chandler knows there is very little hope of getting out of this one without damage. Luckily Joey and Chandler's friendship is miraculously saved but not before Joey gets one punch in for good measure and warning.

4 Phoebe Seduces Chandler

Monica and Chandler managed to keep their relationship hidden for quite a while, but in the episode "The One Where Everybody Finds Out," Chandler is forced to engage in a flirtation with Phoebe to keep the relationship secret. Chandler battles through the awkward encounters and fake date with Phoebe until it all becomes too much.

This is a major episode for Monica and Chandler, one that fans of the show had been waiting for. This situation ties into a long-running plot through many episodes, seeing the pair trying to keep their hook up's quiet from the rest of the group. This is a pivotal moment for Monica and Chandler as their secret is finally out. Fans also finally get to see Chandler develop and grow as a character in his relationships, as he declares his love for Monica.

3 Chandler Kisses Kathy

The episode "The One Where Chandler Crosses The Line," sees Chandler struggling with his feelings for Joey's girlfriend, Kathy. During this episode, Chandler and Kathy share a forbidden kiss, and Chandler is forced to come clean to Joey.

RELATED: The 10 Worst Things Chandler Did To Joey On Friends

This messy situation really puts Joey and Chandler's friendship to the test and is an ongoing plot point for many episodes. Chandler proves himself to be a particularly bad friend in this scenario but is quick to admit and take the punishment for his mistake. Ultimately he is willing to lose Kathy in favor of not losing his best friend, showing growth in his character.

2 Proposal Gone Wrong

In the two-part episode, "The One With The Proposal," both Joey and Chandler pretend to Monica that Chandler hates marriage in an attempt to throw her off the surprise proposal. Chandler's plan completely backfires and Monica is confused, now believing that Chandler doesn't want to commit and her ex, Richard now wants to commit.

Chandler was always commitment-phobic until he fell in love with Monica. This situation really tests him in a scenario where he could choose to walk away when Richard is back in the picture. Chandler believes he has lost his one true love for good until Monica's proposal proves they are the strongest couple.

1 Runaway Groom

In the two-part episode "The One With Monica And Chandler's Wedding," Chandler becomes overwhelmed at the thought of him and Monica becoming the Bings. Scared that he will turn out like his parents, Chandler freaks out and runs out before their wedding.

Chandler's commitment-phobic attitude rears its ugly head one more time. Fans were disappointed to see the old Chandler make an appearance almost jeopardizing his own wedding to Monica. But on this occasion, we see his biggest display of change and growth, as he realizes Monica is the best thing to happen to him. Making way for a new and improved Chandler.

NEXT: 10 Times Monica & Chandler Could Have Gotten Divorced


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