Chandler (Matthew Perry) is the most awkward member of the group in Friends. His sense of humor is his coping mechanism, which can sometimes be self-deprecating. He’s not the best with women (at least until he gets involved with Monica) and one of the show’s recurring jokes is about Chandler’s sexuality.
Chandler’s done plenty of things that have had audiences roaring with laughter, but there are a few that make this list that make us cringe. Everyone has their cringeworthy moments. Yet, Chandler has had far more of those moments than most, 10 of which we’re making a note of here.
Falling Asleep In A Meeting
When Chandler falls asleep in a work meeting, he unknowingly agrees to move to Tulsa. He tries to get out of it, but his boss isn’t impressed by his excuses, so he finds himself commuting from New York to Tulsa every week until he ultimately quits. Still, it sucked that Chandler had to spend so much time on a plane, traveling back and forth, and be away from Monica and the rest of the gang so much.
That kind of schedule takes a toll after a while, so Chandler was right to quit. Still, it goes to show that you should never fall asleep in any meeting, or else you might find yourself moving too.
An Entire Episode Of Cringeworthy
In the first season, Chandler is mortified to discover that upon first impressions, people tend to think he’s gay. It all begins after an incident in which a co-worker tried to set him up with another male co-worker. While the gang simultaneously deals with the death of Ross and Monica’s grandmother, Chandler’s on a mission to clear up his sexuality and set things straight.
Still, the fact that he spends an entire episode debating it with his friends and co-workers, especially when two of his friends have just lost their grandmother, is a little ridiculous, and certainly cringeworthy.
No Smiling For The Camera
Chandler can’t smile for pictures. It seems the pressure of the camera makes Chandler’s facial muscles constrict because outside of the camera he can smile just fine.
It makes for some interesting engagement pictures however, as Chandler looks angry, as though he’s in pain or some other strange concoction of emotions that are generally not seen in engagement photos. No amount of practice works for him, but at least Monica can pull off a good picture for both of them.
Falling Asleep At Joey’s Movie
Joey takes Chandler to his movie premiere as a thank-you for all the years Chandler supported Joey’s acting dream, but Chandler falls asleep and misses the whole thing. Joey is understandably crushed. How could Chandler disappoint his best friend? If he was that tired, why not take a nap beforehand?
The movie premiere is cool in itself, so why would Chandler not force himself to stay awake? Whether it’s a movie premiere or a meeting, Chandler seems to have a difficult time staying awake, and he pays for it later.
Went To Yemen To Ditch Janice
Chandler was once head over heels in love with Janice, but by Season 4 those days are no more. After bumping into Janice at a nail salon, Chandler can’t quite shake her as she’s determined not to let him go again. He fabricates a story that his company is transferring him overseas, thinking it’ll throw her off.
Instead, she helps him pack, takes him to the airport, and insists on staying until his plane takes off. 2100 dollars and a trip to Yemen later, Chandler paid a hefty price for lying instead of attempting to break up with Janice in a more honest manner.
Wearing Girl’s Underpants
When Chandler goes out with Susie (Julia Roberts), a girl he knew from elementary school that he dubbed “Susie Underpants” after an unfortunate incident, Susie decides to exact revenge. Much to Chandler’s misfortune, she tricks him into wearing a pair of her underpants to dinner.
She takes it further when she convinces him she wants him, and they head to the bathroom, only for Susie to steal his clothes and take off, leaving Chandler in an embarrassing situation that ends with him heading out the door with only the underwear and the door to the bathroom stall. He held his head up high the entire time, so we have to give him props for that.
Handcuffed In The Office
When Chandler goes to break up with Joanna, Rachel’s boss at Bloomingdale’s, the break-up goes really well. Joanna gets called away, but forces Chandler to stay in her office by handcuffing him to a chair and leaving him half-naked.
Rachel and Sophie accidentally discover him in Joanna’s office, and from then on Rachel is stuck between letting him go or forcing him to stay, until she strikes a deal with him. Being handcuffed and half-naked in someone else’s office and having a friend find you like that is real friendship, but that doesn’t mean it’s not cringeworthy, so it’s better left forgotten.
Left Ben On A Bus
Granted, Chandler shares this cringeworthy moment with Joey, but it’s pretty bad. Losing your best friend’s kid by leaving them on a bus? It doesn’t show potential for good parenting. No one is perfect, but this is the extreme. Joey and Chandler were distracted by women of course, and they spend pretty much the remainder of the episode trying to find Ben.
They’re good at keeping track of things, as they never forget Ben’s stuff, but people they could use a little work on. We wouldn’t blame Ross if he never trusted them to babysit again, but it’s fair to say they learned their lesson after receiving the scare they did.
Kissing Kathy
Chandler is attracted to Joey’s girlfriend, Kathy, but does everything he can to fight it for Joey’s sake. Chandler’s internal conflict is a source of great stress for him, but it’s nothing compared to the guilt he feels after things get out of hand and he kisses Kathy while she’s still with Joey.
The two of them being alone together while Joey was having car trouble was far from a good idea, but for what it’s worth, they did share chemistry at that point. Chandler later pays his dues in a box at Joey’s request to repair their friendship, but we were cringing from minute one. Going behind your best friend’s back and committing such an act of betrayal is never good, or worth it.
The Engagement Debacle
When Chandler’s ready to propose to Monica, it doesn’t go exactly as planned. In fact, it looks like they’re going to break up for a bit as Chandler convinces Monica that he detests the idea of marriage and will never take the next step in their relationship just as Richard shows up and tells Monica he still loves her. Things get out of hand quickly, and for fans it’s still hard to watch because Chandler and Monica are the perfect couple and we’d never want to see them go their separate ways.
We want to scream at Chandler every time he says something untrue about his views on marriage, as it’s driving Monica away instead of distracting her, which is what Chandler’s actually trying to do so she won’t know of his impending plans to propose. It could have gone better from the beginning, but at least we know it had a happy ending.
