Perhaps, the most common conclusion drawn online is that Nate, the boyfriend to the aspiring journalist heroine Andy, is the true antagonist, since he is portrayed sympathetically despite being an unsupportive partner and an overall drag. But then, there’s the obvious choice of Miranda, the bad boss to end all mid-aughts bad bosses, or Emily, Andy’s fellow assistant who papers over her heart of gold with a significant mean streak, or Christian, the condescending magazine writer with whom Andy shares a brief fling.

NJ: A simple boomer unable to understand why their millennial child is working overwhelming hours for little pay! At least he offers her money and to see Chicago. 

MC: Andy’s dad’s whole thing is that he doesn’t know why his daughter turned down graduate school at Stanford to accept a job that she hates. That’s a fair question, though he does unfortunately align with the belief that this gig is a waste of time, aka Nate-ism. I know everyone’s weird about the fashion magazine thing, but to this day, I don’t understand how a freshly graduated journalism major getting a job as the personal assistant to one of the most powerful editors in the business is somehow a step down. A step down from what? She graduated, like, 20 minutes ago! 

NJ: Jacqueline jumps at the work opportunities offered to her, and I do not begrudge her for it.

MC: She’s here for cash and intrigue, and cash and intrigue only. 

MC: Doug participates in the theft of Andy’s phone, which we’ll get to momentarily, but with only a few lines, he establishes himself as way more knowledgable about — and, perhaps more importantly, respectful of — the fashion industry than Nate, who for some reason decides to take a brave stand against owning multiple purses? Luckily, Doug will have none of that. 

NJ: He sucks the least out of Andy’s friends, which is quite tragic when you think about it.

MC: Lily’s a good friend who likes labels and people not cheating on their significant others, and hey, who among us doesn’t? Like the rest of Andy’s friends, she’s skeptical about whether this job is good for her, but she probably should be, what with the fact that it’s a terrible working environment. But she does participate in one of the film’s most unforgivable acts — when Andy’s friends play hot potato with her phone while she’s getting a call from Miranda — and that scene sends a chill down my spine. 

NJ: Did we watch the same movie? I disagree here. I don’t think Lily is a good friend. I think she’s SUPER judgmental of her friend evolving in her first job post-college — she’s fine to accept the Marc Jacobs bag, but then gets all mad when Andy herself shows interest in fashion? Hello??? She is also SO sanctimonious over Andy flirting with Christian, like, “The Andy I know is madly in love with Nate” — I’m not saying that Andy is in the right here, but at least maybe ASK HER what’s going on before shouting at your friend. 

MC: I see what you mean about talking to Andy before shouting — I am, in a general sense, opposed to shouting — but I think I always interpreted Lily as being friends to both Andy and Nate, and not just Andy, who happens to be dating Nate. In that case, I think it makes more sense for Lily to get upset in the moment, since she thinks one of her friends is being unkind to another. 

NJ: I think Giselle only has four lines in this movie — two of which are mean, two of which are nice. A true neutral.

MC: I didn’t see this movie in theaters, but I hope that people reacted to the “you look good” line by cheering. 

NJ: Poor Emily. I think I’d burst a blood vessel if I saw someone who didn’t care about their job out-perform me while I was killing myself for it. Admittedly, she is quite mean! I would be, too, if I couldn’t go to the bathroom when I wanted.

MC: Emily’s job is her life, and once Andy starts taking hers seriously, their relationship thaws to the point of near-friendship. The whole Paris debacle is a roadblock, but I like to think that after Andy quits and offers Emily her clothes as an olive branch, the pair meet for awkward cocktails once every six months. 

MC: I have a phobia of expensive New York grocery stores that I’m trying to work through. Also, berries are so expensive, and then sometimes you eat the top layer of the container, and the ones at the bottom are squishy and moldy already, even though you only bought them, like, yesterday, but now you’re the fool for letting fruit get the best of you and go out on its own terms. Sorry, that’s another thing I’m trying to work through. 

NJ: I accidentally spent over $10 on strawberries the other week, I feel you.

NJ: I remember re-watching this movie for the thousandth time around the time that I interviewed at [REDACTED] for an internship at [REDACTED LARGE PUBLISHING HOUSE] and would have done just about anything to get it. At this time, I found Andy’s character INFURIATING. Watching her show up to an interview without knowing anything about the magazine or the publishing legend felt like a personal assault. At the same time, I don’t want to glorify toxic “pay your dues” culture by saying something like, “Suck it up for a year Andy, I had to hand vacuum rugs for no money” because that was also wrong.

MC: When I worked in a gift shop in high school and college, my interview went something like this. 

Gift Shop: Do you know anyone who wants a job? 

Me: I do!

Gift Shop: You’re hired. 

Somehow, Andy thought that would be her Runway interview. But she’s on an upswing from that point onwards, and watching this movie in an era where everyone with a job is questioning their long-term prospects, it’s more relatable than ever to see someone with a “dream job” realize that hey, it’s not all that great. 

MC: James double-crossed Nigel, and for that, I cannot forgive him. Also, he absolutely deserved Miranda’s pursed lips for his weird bowtie dress. 

NJ: Honestly, I had never considered any double-crossing. Sure, I guess a heads up to Nigel would have been nice. But let’s not forget that he also offered Andy a drink at his fancy party!

MC: True, but where is Nigel’s drink? (By drink I mean job.) 

MC: “You can leave the book with us,” the lying liars lied. These two don’t deserve exclusive access to highly anticipated works of wizard fiction, nor do they deserve “surf boards, or boogie boards, or something for spring break.” And yet, they get both. They’re just kids, but I just know these two would grow into the interns with professional connections who even your boss fears. 

NJ: Trolling the assistant is a family sport! I can see at least one of the twins making headlines in the future for not knowing how to chop a cucumber.

NJ: IT ALL GOES BACK TO IRV.

MC: My favorite thing about Irv is that he was defeated through Miranda handing him a typed list of names. List writers everywhere crave such power. But yeah, he was playing chess, and Miranda was also playing chess, but on one of those boards that has, like, four levels. Sorry, Irv. 

NJ: Miranda is brilliant at her job. She is undoubtedly the victim of a patriarchal system which doesn’t acknowledge her brilliance while simultaneously demands her perfection. She even helps Andy get a new role after she quits on short notice. Simultaneously, she also makes unreasonable demands, is terrible at training new employees, and fosters a frightening work environment. I’m always drawn to what Andy says about Miranda — “If Miranda were a man, no one would notice anything about her except for how great she is at her job.” Just think of all the men we glorify in Hollywood who are KNOWN for belittling, screaming at, and even assaulting their employees. Capitalism, baby!!!

MC: Miranda is that intoxicating (and toxic) combo of “she might be a monster” and “I crave her approval so hard that it causes me physical pain.” But no matter your job title, or how much of a “genius” you are, I don’t think it’s ever acceptable to treat people the way Miranda does. Her most benevolent act is guaranteeing Andy a new job after Andy walks away, and giving a little chuckle after she sees her ex-assistant walk by the office, but then she immediately yells at her personal driver, because Miranda mistreats all of her employees on the basis of the fact that she thinks they should be “grateful” to work for her. Andy got out, but not everyone is so lucky, and no matter her level of inpidual achievement, her misuse of institutional power is what stands out to me. Now, you might be thinking I’m taking a fictional character from a 2006 rom-com too seriously, but then again, have you seen the rest of this list? 

NJ: I think it’s important to establish here that Christian is in a position of power over Andy in this movie. He’s an acclaimed journalist with immense industry sway (he gets the Harry Potter manuscript, for crying out loud) — while Andy has just graduated college, is at least a decade younger than him, and is at the bottom of the editorial ladder. This, in and of itself, is enough to make the dynamic between them uncomfortable, but IMHO the worst thing he does is sleep with her without telling her that he was on track to be the new editorial lead of Runway. I personally don’t care that he “betrayed” Miranda, but if Jacqueline DID become the new EIC (and Andy stayed on), then Christian would become her formal superior at work. That feels like gross information to withhold to me!!!

MC: Excellent point that I never thought about before. +1 from me to Natasha on this one. 

NJ: Nate, Nate, Nate. Where to begin? He constantly makes mean (and sexist!) comments about Andy’s appearance and the fashion industry. Although he is (allegedly) a chef in New York City, he cannot fathom that his girlfriend often has to work unreasonable hours for… One! Year! I understand him being upset at Andy missing his birthday — I would be, too — but the way he goes about it makes him seem like a pissy man-child. He actually would be a fantastic character if the point was to show two lovers growing apart post-college entering the “real world” — but then just Andy has to go and apologize to him after.

MC: I never considered the fact that he’s a chef and would therefore definitely be working long hours (and, depending on where he was hired, in environments just as snooty or high-pressure as Runway). But yeah, Nate’s constant stream of passive aggressive and just plain mean comments to Andy makes me less than sympathetic to him, and I wish they’d just broken up and moved on at the end of the movie, instead of implying that they’d try to make long-distance work. That being said, he does make Andy fancy grilled cheeses (and complain about how expensive they are, but hey, that’s on Dean & DeLuca). 

NJ: Even 16 years later, the exploration of “pay your dues” culture in journalism still feels relevant. And I’m not just saying that because I’ve also had to run garment bags across the city and fetch Starbucks in a state of emotional distress.

MC: There’s no one human being who can do more damage than American workplace culture as a whole.