Each of the six main characters of Friends, alongside multiple recurring characters, has become beloved and iconic in the pop culture sphere over the past two and a half decades since the show's debut, but arguably none are at the level of Chandler Bing. He is challenged only by Rachel in of overall arc and growth and is consistently the show's funniest character.
Chandler undergoes a huge amount of development over the 10 seasons of the show, and while at his core, he is the same sarcastic, loving, immature friend, so much changes about him and his life. If he had a chance to look into his future, there are many aspects of the final version of Chandler that he would have felt a sense of pride about, and yet he'd be sure to feel severe annoyance about others.
Hate: Not Living With Or Near Joey
For the show's entire decade span, and for some time before the show's on-screen story, the main gang all lived extremely close to one another, with the two most consistent characters in this regard being Chandler and Joey.
When Joey leaves for his own apartment in the early seasons, it breaks Chandler's heart. Chandler, from season one, could not imagine living without Joey, nevermind living with a significant other and all the commitment and responsibility that comes with that. The fact Joey moved to Los Angeles would be incomprehensible to a season one Chandler, who was pretty much ed at the hip with Joey.
Proud: He Avoided Janice
While Ross and Rachel are perhaps the most iconic will-they-won't-they couple in television history, Friends had another on-off relationship for the first few seasons between Chandler and Janice.
Chandler only really loved Janice once - the rest of their time together was Chandler hastily rushing back into seeing her before finding some ludicrous way out. Season one Chandler made his true feelings of Janice, personality-wise, very clear, and in the first few seasons of the show, he pretty much used her to escape loneliness. The fact that finale Chandler, nevermind being in a long-term relationship, simply managed to avoid Janice and never get back together with her after his trip to Yemen would make season one Chandler proud.
Hate: He Missed Joey's Big Break
Throughout the show, Chandler does some pretty awful stuff to Joey, especially considering the good Joey always tries to bring to Chandler's life. But the one bad thing Chandler does that season one Chandler would frown upon the most comes with Joey's big break.
Even in season one, when Joey was at his lowest point as an actor, Chandler was consistently helping out with his career, enjoying doing so. For all his maturity issues, he was desperate to see Joey succeed. Had he known Joey would star in his own movie, he would be over the moon, and the fact he managed to miss the premiere would have disappointed season one Chandler to no end.
Proud: He Overcame His Fears
Chandler's job is the source of much hilarity throughout Friends, and from not knowing what he does to his unwavering hatred of his job, him leaving his job was a long time coming.
When Rachel is looking to quit her job as a waitress, Chandler tells her about the fear, the thing stopping people from leaving jobs they hate, including him. Very late in the show, Chandler overcomes this fear and leaves his office job to pursue something he actually wants to do. Season one Chandler simply would not care what he went on to do, as long as it was not statistical analysis and data reconfiguration.
Hate: He Never Got Real Closure With His Family
Chandler's family life is the butt of many jokes in Friends and is the source of so many problems for the character, which he makes abundantly clear in the early seasons of the show, particularly when we meet his mother, Nora, and see his father in flashbacks.
Chandler is pretty clear in the fact he wishes he did not have an upbringing like the one he did, and even though he eventually gets in touch with his father and both his parents turn up at his wedding, he never really gets any closure on that past. He treats his father in a subpar way, he is never seen speaking to his mother, and while season one Chandler does blame them for a lot of his problems, he still does wish he had some sort of decent relationship with them, which he never gets, or even tries to get.
Proud: He Dealt With A Lot Of His Insecurities
Of all the characters at the start of the show, Chandler was the one who was not only the most immature but also had the most insecurities and issues, such as his use of humor as a coping mechanism and his fear of commitment.
He was fairly aware of this in season one and knew it definitely affected his relationships, both romantic and otherwise, as well as how he coped with life and its responsibilities. He did not necessarily like how he had all of these issues, he was just used to them, and as such, knowing that he managed to overcome so many of them would make him proud of himself.
Hate: All His Responsibility
The difference between season one and season 10 Chandler is truly astronomical. While he is still the sarcastic, fun, popular, and charmingly awkward friend, he has toned all that down and is now a mature adult, something season one Chandler would not be able to handle.
Season one Chandler enjoyed spending his days on the Barcaloungers with Joey, binging Baywatch and other random shows, eating insane amounts of takeout food, and having no care in the world. He could not handle responsibility well, scared of commitment of any kind. While finale Chandler dealt with the responsibility he had well, had pilot Chandler been told about this responsibility, he would immediately be out the door.
Proud: He Didn't End Up Alone
Monica was a huge turning point in Chandler's life. His secret fling-turned-relationship-turned-lifelong-love-story with his friend changed him for the better in so many ways, helping him get over a lot of his issues and make him happier in the long term.
Chandler would have always been happy with anyone he fell in love with as long as it was mutual. Season one Chandler and Chandler pre-Monica in general always made clear his desperation to find love and the fact he was scared of ending up alone like Mr. Heckles.
Hate: He Treated Joey Like A Child
There is no better duo, romantic or platonic, in Friends than Joey and Chandler. They are hilarious, and their bromance made for emotional, touching moments and some of the most memorable scenes of the show.
As the show progresses, though, for some reason, Joey gets much dumber. He was not the smartest individual in the first few seasons, but it became much worse, and Chandler's attitude towards him likewise. Whereas before the two were a duo of immature adults who enjoyed the same lazy activities and were happy doing so, that dynamic became more of Chandler treating Joey like a child. Season one Chandler would still make the sarcastic quips at Joey, but they were equals, and he would have been bummed out if the future changed that dynamic as it did.
Proud: His Family Life
It was a shock to audiences and characters alike when it was revealed that Chandler and Monica could not have biological kids together, and it definitely left everyone wondering if they would start a family during the show's time.
Thankfully, they adopted twins and led a stable, old-fashioned family life in the suburbs. In general, season one Chandler and early Chandler was always vocal about the effects his family life growing up had on him, being the source of much of his insecurity. He would be proud of the fact he managed to provide a stable life for his children with a partner and a full home.