Pretty Woman is an absolute classic when it comes to romantic comedy, but it's also a film that definitely hasn't aged well. While some hold it up as the ultimate wish-fulfillment (shopping trips, relaxing, ultimate comebacks to snobby salespeople, all ending with an uber-rich Prince Charming), others deride it for outdated gender roles, Edward 'saving' Vivian, and problematic portrayals of sex workers.
If Pretty Woman was to get a remake today, it would certainly look different. Obviously, the cast would have to change, but in addition to that, what would be the most noticeable changes made to bring it up to date, but keep the central story of a sex worker bringing out the best in an emotionally shut-off executive, and falling in love?
10 The Lack of Diversity
Pretty Woman is set in LA, yet the film is painfully white, with essentially the only POC in the film being Latinx prostitute Kit and hotel manager Barney. Beyond this, BIPOC cast members are in unnamed roles like 'Happy Man' and 'Japanese Businessman'. This isn't reflective of LA (or the world in general), and one of the first things to change would be to add some much-needed diversity to the main cast.
9 Edward's Treatment Of Support Staff
It's played as a bit of a funny quirk, and something that shows just how high-powered, busy, and wealthy Edward is, but he simply doesn't treat servers or shop assistants with the kind of respect that modern audiences would want. At this point in time, showing a wealthy person being dismissive or demanding of retail staff (even if they aren't being outright rude) is a great way to set up a villain... not a romantic lead. Vivian herself would also presumably be less impressed with his shenanigans of talking down to the people who help him, or outright demanding 'sucking up' because of his money. If this wasn't omitted entirely, it would be good to see her calling him out on it, and reminding him that his money shouldn't come with a side of rudeness to the staff.
8 The Lavish Lifestyle
In Pretty Woman, Edward is said to be living the ultimate luxury-executive lifestyle, but by modern standards, it's actually not that lavish at all. He rents an extremely expensive car, stays at a nice hotel, has some nice dinners, and goes to a polo match. While this was undoubtedly impressive in 1990, luxe living in LA in 2021 is on a whole new level.
The rental car does allow for their meet-cute, which is a key part of the story, but Edward wouldn't just have a penthouse suite, he would have an army of assistants - personal chef and trainer, maybe, and they would certainly be enjoying an upgrade on that lifestyle, if Edward only wants 'the best'.
7 The Fashion
This is a bit of an obvious one, but an important one, nonetheless. The fashion is a huge part of the appeal of Pretty Woman, and it would have to get a makeover. Edward's boring-but-expensive suits could potentially stay, but Vivian's spending sprees would ditch the shoulder pads and bring in some modern designer clothing.
6 The Gender Roles
As well as lacking diversity, the original Pretty Woman is also frustratingly traditional when it comes to gender roles. Businessmen and management are male, while retail workers and servers are female. It's extremely outdated and frustrating - and a remake would have to play with this. It would be fantastic to see Vivian's attendance at Edward's business dinner involve actually connecting with a powerful woman, rather than charming an old man with her helplessness, for one thing.
5 The Event They Attend
It's been mentioned once already, but attending a polo match really needs an entry all its own. While this was a very 'classy' event to attend at the time, it's not exactly the best networking opportunity these days. Instead, it would be likely that Edward would take Vivian to some kind of exclusive event, with far more entertainment than 'stomping the divots'. A major event would also likely end up with a lot more press and social media coverage - another element lacking in the original film.
4 The Technology
While on the subject of social media, another obvious upgrade would have to be the technology. While Vivian wearing her headphones in the tub is now an iconic scene, she'd be more likely to have an in-suite sound system in the penthouse these days.
Edward's cellphone would definitely get smaller, and he would likely be stressing out about appearing with Vivian on someone's social media account. While this may seem like a simple switch, it could cause some fairly big changes to some aspects of the film - especially online speculation, or Edward dealing with a social media manager who is less than thrilled with his date-for-the-week and the questions she will raise.
3 Kit and Vivan's Friendship
Kit is a character who has so much potential in the original film, and it's just not fulfilled. Vivian's best friend and roommate, in the original, Kit exists largely as a cautionary tale - and a way of making the point that Vivian is 'different' from other sex workers. While Kit is clearly an addict, has no real goals in life, and hangs around seedy clubs, Vivian is the one who never does drugs and just wants to pay rent. Instead of this two-dimensional portrait, it would be nice to see Kit fleshed out, becoming a real friend to Vivian (not just someone who pops up to take money and congratulate her on her good fortune). Seeing a positive female friendship would add so much to the movie, and it's a shame Kit didn't get a chance to shine.
2 The Treatment Of Sexual Assault
When Edward loses a deal, his lawyer shows up to have it out with him, and instead ends up assaulting Vivian, only being stopped when Edward shows up and throws him out. This does have the potential to be used to shine a light on how a certain type of person views a sex worker as an object to be simply bought or used, but it's not quite fully explored enough to do that in the original. Instead, it is used as a way to show how Vivian is used to being abused (given her comments about how men 'always know' where to hit), and that it is up to Edward to save her.
1 The White Knighting
The most frustrating element of the film is the portrayal of sex workers - and the idea that what Vivian really wants is for a white knight to show up and save her from her terrible life. Throughout, Vivian is portrayed as street smart, but ultimately clueless and charmingly ignorant, while Edward educates and then 'saves' her in the end. (And of course, all the other sex workers encountered in the film are seen as addicts and low-lives, while Vivian is the exception.) Instead, it would be nice to see an updated version of the film able to portray the humanity and complexity of sex workers, and to find a balance between suggesting that Vivian might like someone to come and give her a boost out of subsistence sex work, but is more than a helpless woman who can't change her life without a man.