The troubling thing about Margaret's "punishment" is the implication that she deserves it in the first place.
The Proposal begins with what looks like a surprise. Sandra Bullock plays against type, as the powerful, ruthless, oh, and single, executive editor Margaret. The ultimate castrating bitch, she's left a trail of dead (men's) careers in her wake. There isn't much to differentiate her from that other corporate Medusa, Miranda Priestly from 2006's The Devil Wears Prada.
But Margaret inexplicably loses her footing when she learns threatened with deportation back to Canada. First, she makes a ridiculous decision, to demand that her long-suffering assistant Andrew (Ryan Reynolds, as terminally cute as Bullock, in his way) marry her to solve her green card problems. Second, though she's puzzled when he has the guts to make his own demand (that she grant him an overdue promotion in return for committing a felony), she agrees. From this moment on, as they travel to Alaska to meet his family and convince them the relationship is for real, the point of The Proposal is Margaret's punishment and redemption by true love. Of course, Andrew is the source of Margaret's transformation into an acceptable woman since this will also secure his own status as a man (as "whipped secretary" is apparently less than ideal). For Margaret, the process involves multiple physical humiliations, frequent silencings and the requisite realization of her feelings for Andrew.
The troubling thing about Margaret's "punishment" is the implication that she deserves it in the first place. Sure, she's pushy and demanding, even harsh, but she's also hugely successful, much to the appreciation of her bosses (Michael Nouri and Dale Place). When she fires Bob (Aasif Mandvi), he shrieks in response that she's a "poisonous bitch" in front of the entire staff. The scene is laid out to suggest that even though she can be cold, at the same time, he deserves to be fired. When Margaret later admits that Bob's name-calling made her cry, we get the point that she has a heart, but because she doesn't show it like a proper girl, she must be schooled.
On the other hand, Andrew is wholly without fault. In the beginning, we excuse his butt-kissing since he is openly self-loathing on this point and further ingratiates himself to his office mates (and us) by warning of Margaret's approach with such witty IM's as "It's coming" or "The witch is on her broom," so they can scurry into various poses of busyness before she passes. He rarely visits his doting mother (Mary Steenburgen) and grandmother (Betty White), but that's because his father (Craig T. Nelson) in an overbearing, unmitigated jerk. Andrew is just as self-serving as Margaret, happy to blackmail her to get that promotion, but again, we know that in truth he's earned it, so his craven ambition is excused as well.
Most unsettling, though, is the way the movie positions Andrew's new and righteous power over Margaret as a source of humor. So, when he forces her to get on her knee to propose properly, he makes her agony into his comical triumph: "Your heard me. On your knee." She gets on both knees, thanks to her skintight skirt. And when he finally admits his own feelings, cutting off her ramblings with "Margaret! Stop talking!" his demand is punctuated by coworkers shouting their support with "Show her who's boss, Andrew!" In all this, The Proposal is tired and unimaginative at best, and openly misogynistic at worst. And no amount of cuteness makes up for either.