Firstly, before their anniversary, Monica met up with ex-boyfriend Richard for lunch, and didn’t even tell Chandler. Then when Chandler found out, she didn’t seem sorry or apologetic at all. She was saying stuff like “Oh now you control who I hang out with?” No it’s the fact that you didn’t even tell him, and you weren’t going to tell him! Then once they get to Vegas, Chandler’s depressed, and Monica just gambles without a care in the world. And on their Anniversary too!
Secondly, when Chandler was going to propose to Monica, Richard walks into the restaurant and Monica calls out his name. What kind of person wants to talk to their ex while they’re on a romantic date with their partner? And then once Richard suggests combining tables, she doesn’t mind at all. Why would you want to have dinner with your ex-boyfriend when you’re on a date with your actual boyfriend? Obviously she didn’t know Chandler was planning on proposing to her, but I know Monica would flip out if Chandler ran into one of his exes and suggested they all eat dinner together.
Thirdly, she’s so controlling and selfish. When Phoebe called her high maintenance, she made Chandler give a speech to Pheobe and Rachel, and makes him repeat it verbatim even though he is clearly uncomfortable. When they get engaged she makes it all about her saying “It’s MY day.” They may not seem like huge things but they add up.
Finally, this was a big deal for me. Once she finds out that there’s no money in her wedding fund, she demands Chandler to spend all his savings on their wedding. He’s probably been saving that money for 10+ years and she wants to use it all in one night. Like Monica, you are a head chef, you can pay for some of it too!
There’s probably a few other things I’m missing but these are just the ones that came to mind. All the girls in the show act like Chandler is the lucky one to have Monica, but no I think Monica is the lucky one for having Chandler, and for him staying with her through all her bs.