1. Nigel
2. James Holt
3. Doug

4. Lily

5. Andrea
6. Emily
7. Miranda
8. Christian Thompson

9. Caroline and Cassidy

We all love Nigel, but what about Nate?
Nigel is the least problematic and basically the only truly kind and professional human being at Runway. Not only does he know how to do his job, he gives Andy a true reality check without being mean. Also, the way he handled his job being given to someone else? Iconic. This man is literally the only person I would want to be friends with in this entire film.
Though James Holt seems like quite a nice guy, he knew that Nigel's job would be given to Jacqueline and didn't tell him. Besides that, he wasn't problematic at all and was kind to Andy when he first met her.
Out of all the people in the friend group, Doug seems like the least problematic. Though he made fun of certain aspects of Andy's job, he never judged her for it, and he supported all of her changes.
Though Lily has had her good moments, she was judgmental of Andy until she got some perks from her job. Yes, Andy did deserve to be told off when Christian kissed her in Lily's gallery, but she didn't need a speech about how bad it would be if she couldn't come to Nate's birthday party.
I only felt it was appropriate to put Andy about halfway down the list. She definitely isn't the post problematic, but she has her moments. Especially at the beginning of the film where she's incredibly judgmental about the people who work at Runway. And like Miranda told her at the end, she became ruthless because of the job and snubbed the opportunity for Emily to go to Paris.
Like all the others at Runway, Emily was just trying to do her high-pressure job in a toxic environment. However, that does not take away from the fact that she was mean to (and was fat shaming) Andy throughout the course of the movie. Still, she's the only Emily that deserved to be in Paris.
Yes, she's an iconic character, but does that mean she isn't problematic? No. Though most of the demands that she makes seem reasonable, some are just ridiculous like the need to fly home during a storm. And let's just address that she gave away a massive opportunity that could've gone to one of her best employees just to save her own skin. However, though she obviously disliked that Andy quit, she did write her an honest recommendation for all the hard work.
Christian flirted (heavily) with Andy when he knew she was still in a relationship. The only reason he isn't lower on the list is because he did pull through with the manuscripts and really helped Andy when she needed it. He's still kind of a creep though.
The twins! These girls are half of the reason why Miranda makes ridiculous requests. They also got Andy into massive trouble just for fun. Who does that? The reason why they're this low on the list is because all they did was cause trouble.
And finally, of course, Nate. Do I even have to explain this one? He was rude to Andy throughout the entirety of the film, making rude comments about her job, her new colleagues, and how she changed as a person. He was honestly the worst boyfriend in cinematic history, and the most problematic in the film.