The Proposal was the first romcom I remember loving, not just because my mom loved it and showed it to me, but because it felt like everything I wanted in a movie. I was 12 in 2009, the perfect age to fall for Sandra Bullock and Ryan Reynolds on screen. Plus, I had been to Sitka, Alaska the year before and was THRILLED to see it on screen, even though (to my dismay) this movie was filmed mostly in Massachusetts. Even though I have a deep love for this movie, I think it’s worth examining in the context of how this movie deals with the often-portrayed interoffice romance. Margaret (Bullock), the editor of a publishing company, has a male assistant (Reynolds) instead of a female assistant to torture, which is an interesting take on the tropes usually associated with the mean female boss character.

 

That bitch boss character, while present in a lot of romcoms, is rarely the female lead — she’s usually a character in the background, meant to stir up trouble for the heroine who works for her. But, this film puts the bitchy boss at the center of the romantic action, choosing to humanize her through a relationship with a man. This is a romantic comedy in the truest sense: lots of rom, lots of com, plenty of reasons for the couple not to be together before they inevitably are. It indulges in a lot of classic tropes (enemies to lovers! Fake dating!) while also poking at them a little. And it’s just fun, y’all.

 

Margaret Tate is a classic bitchy romcom boss, and as such, the film uses the common language of tropes to establish her as the type of character with which the audience would be familiar. The opening shots of the film are of Margaret hard at work, reading a manuscript while working out on a stationary bike. Then, she’s reading a manuscript while eating her cereal! Like many bosses in romcom land, she doesn’t seem to have a life outside of work. When she finally gets to the office, it’s a classic “the bitch is coming” scenario — her underling scatter in the publishing office to get her coffee and appear like they are doing work. Like Miranda Priestly and unlike some romcom bosses before her (think How to Lose a Guy in 10 Days), Margaret is actually good at her job. She gets the mythical “Frank” to do Oprah, something her male coworker couldn’t do. However, she’s very much disliked by people in her office, something that sets her apart from the hero worship of Miranda in The Devil Wears Prada.

 

This is an interesting take, because usually the boss bitch is actually liked by other people in the office who work to try to convince the assistant character that the boss is actually good at her job, even if she rains down abuse. When Bob yells at Margaret that she is a monster and “has no semblance of a life outside of this office,” does anyone think differently? Certainly, no one jumps in to defend her, especially Andrew. This circles around something we see pretty often in the romcom working world, that women who are only into their careers and nothing else are somehow missing out on “life,” which I’m not super into. Although we later learn the depth of Margaret’s loneliness, in this moment, she seems content with the career-driven life she leads. Which, of course, means she’s headed for a romantic relationship by the time the credits roll.

 

While watching, I couldn’t help but think about how Margaret’s relationship with Andrew adds a new layer to the stereotypical boss/assistant relationship that we often see in a romcom. She’s unapologetically in charge, and she doesn’t need him to affirm her position at work — she tells him, not without snark, that if she wanted his praise, she would have asked for it.” As she pushes him around at work, I found myself getting kind of a cathartic thrill out of it, rather than feeling sorry for Andrew. Maybe it’s because I know how this movie ends for the two of them, or maybe because even as her put-upon assistant, Andrew is still insulated by a level of privilege. As we later find out, his family is hella rich. And there is this sense that Andrew would be just fine without this job, although I can’t know that to be true. Still, he has absolutely zero power in his relationship with Margaret. When she asks him to work the weekend, there is no way he can say no.

 

He also can’t say no to her other request, which is to fake marry her so she isn’t deported back to Canada. This, I think, is where Margaret’s abuse of Andrew ceases to be fun for me. Perhaps it’s because deportation played for laughs just feels hollow in 2019, but I think it’s also because she’s asking him to commit a felony for a job. And I mean, check back with me after graduation and I’m still unemployed, but there are some things you just shouldn't be willing to do for a job in publishing. Is it an abuse of power that she makes him do this? Absolutely. Would this be totally creepy if she were the assistant and he were the boss making this request? Yeah, probably. It’s an interesting look at the inter-office romance that would terrify HR, at the very least. I know this is the device that will ultimately get these two together, but watching this again, I feel so bad for Andrew. I also feel bad for Margaret, thinking that this is her only desperate choice to keep a job where most of her coworkers hate her.

 

When they get to Alaska for Andrew’s grandmother’s 90th birthday (the way they’re going to convince the authorities this marriage isn’t a sham), his family is understandably confused as to why he’s dating and engaged to his horrible boss. They also seem to belittle her career and the publishing industry as a way of digging at Andrew. Someone asks, “I’ve always wondered, what does a book editor do?” to which his dad replies “Maggie here is the editor, Andrew is the assistant.” Also, sir, she did not say you could call her Maggie. She’s not a child, she’s a successful woman. His dad also accuses Andrew of sleeping his way to the middle, insinuating that he is with Margaret for some kind of career advancement.

 

Which, ironically, he is. She was strong armed into agreeing to give him a promotion and publish the manuscript he’s been championing if he goes through with this fake marriage for her. Honestly, not a bad deal. This is an interesting direction for the film that I wish they explored more. Usually, it’s when a woman has career advancement that she is accused of sleeping with people in power to get it. By flipping this on its head, this movie had a chance to point out the hypocrisy in such a statement, as this time the accusation is kind of true for a man.

 

Margaret can’t leave the job she’s in danger of losing behind, even all when she’s on the literal opposite coast. Even when she’s supposed to be making nice with Andrew’s family, she’s trying to work. She’s constantly trying to get a cell signal to talk to Frank on the phone. Her devotion to her job is sharply contrasted with Andrew’s apathy in regards to the family business in Sitka, Alaska that he’s supposed to take over. It’s a similar vibe to the “it’s not my dream Dad, it’s yours,” rhetoric of every teen movie ever, but the scale is a little different. Try as hard as this movie might, I just don’t believe that owning a general store and an internet cafe in Sitka, Alaska, is the type of family empire Andrew should feel ashamed to leave behind. He protests with his family, saying that his job makes him happy, even if his parents don’t understand. I have two thoughts about this: one, does this job make Margaret happy? Is happiness the goal of a career? Also, is this kind of idea inherently coded as feminine: pursuing a job because it’s “what makes me happy?” I’m not sure about either.

 

Andrew and Margaret begin to fall for each other amid the accidental nudity, adventures in the Alaskan wild, and Margaret’s inability to dress for the activity, because of course they do. She begins to express hesitation and guilt about how this sham marriage will affect his sweet family (think of Betty White, people!), but Andrew just commits harder. At this point, I don’t think either of them are acting out of purely career-based motives. We’ve watched Margaret become more of a human being, rather than a bitchy boss trope, through her relationship with Andrew, a direction in which movies with this trope rarely choose to go. Her career was what motivated this relationship to begin with, and now that she actually begins to care for Andrew, she is willing to give it up.

 

Normally, I would rail against a woman having to give up her career for a man, but this is so much more complicated than that. In the context of their situation, giving up her career is a measure of character growth. Also, because it maybe needs to be said again: no job is worth committing a felony for. Just take the “L” and go back to Canada. In the end, the calls off the wedding at the altar. She leaves him a note, complimenting his work at the office (which, now that I’m thinking about it, I can’t remember him ever saying that about her), saying she now realized it wasn’t as easy to ruin his life as she thought it would be. It was a business deal, ad now the deal is off. She promises to publish his manuscript before she leaves the publishing house. Apparently, she know the book was special all along and didn’t want to publish it and lose him as an assistant. Again, it’s that same kind of manipulation that leaves me feeling uneasy, but the film is hurtling toward a romantic conclusion and doesn’t have any time to ponder past-Margaret’s bad behavior. On we move.

 

In the end, Andrew’s mom and grandma are right — if Margaret didn’t love him, she wouldn’t have left him. This is definitely evidence of a change in Margaret from the beginning of the film, who would never have made this choice. And, it seems like growth for Andrew, too. But the growth isn’t as pure as Margaret’s, the movie makes the case that what Andrew needs to do now is chase this woman and not honor the choice she made to leave him. Her needs to become her boss, in effect, for her to be with him. When it comes down to it, a film that was willing to explore a new storyline for a common trope and tackle a new gender dynamic in a working relationship where the man isn’t the one initially in power isn’t OK with subverting some stereotypes. Yes, I love love, but a a guy shouting “show her who’s boss, Andrew” while the two kiss in the office doesn’t sit all that well with me. Can they be equal, at least? And will he still get that promotion? I kind of hope he would, at least to even out their ever-fluctuating power dynamic. Someone call HR.