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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.