Pretty Woman is older than I am. That slightly blew my mind (even if it is only by a few days). Still, considering the pedigree, it held up pretty well (heh). Would this movie be made today? Probably not in the same way, no, but it isn't a horrific stab at the subject matter and at least the most problematic character isn't either of the sex workers.
I think the biggest issue with the movie is that the main subtext around wealth is both slightly undermined by the conclusion and the supposed love interest. That is, the film pretty bluntly attempts to deconstruct the notion of American exceptionalism, that the wealthy are wealthy because they are somehow better than everyone else. That they're maybe more intelligent, maybe more hard-working, maybe just more lucky, but more something, certainly. Yet here comes this "lowly" sex worker, someone viewed by society as an abject dropout and dead-end, who not only shows a significant degree of intelligence and adaptability, but in many ways shows up the ultra-rich characters around her. She's more ethical, more switched on, and (of course, because Hollywood) more beautiful, both inside and out. Heck, the hotel manager (a brilliant character and one of many recurring/overlapping castings with The Princess Diaries) pretty much states as much. He's a person who operates entirely within the world of wealth without actually being a part of it, so is able to shine a proverbial light on things.
And to a degree, the film makes this claim successfully. Yet it still paints the picture of wealth being the ultimate and most important goal; it still shows the concept of ultra-wealth as somehow desirable on a personal and societal level; and it never really allows Julie Roberts to truly shove her superiority in everyone elses face. And all because she needs to fall in love with the utterly unlikeable Richard Gere. I mean, come on, there are zero redeeming qualities here. He's born rich, turned that privilege into a way to destroy other people's companies, is seemingly incapable of empathising with other humans, genuinely only cares about money, and even by the end of the film is still unable to promise to be anything more than an egotistical, semi-sociopathic, misogynist and classist. Sure, he defends her from rape (by his "best friend"), then treats her like a disposable object or pet, never really apologises (just claims that's "who he is"), and instead performs a single romantic grand gesture that doesn't resolve any of the valid reasons she left him. All that does is undercut her autonomy and intelligence. She was about to go back into education and turn her life around: let her!
(And that's before the problematic notions of women needing to be "saved" by gallant Knights... dammit, you came so close! 😂)
Ultimately, that's my biggest issue with the film. The side characters are all interesting (if 2D), the casting is great, it's fun getting to see a more energetic and youthful performance from Julie Roberts (who is generally brilliant throughout), and for the time it must have been shockingly progressive. That last part will obviously have paled a little, but it hasn't fallen into the trap of being overtly sexist or problematic, which shows that care was taken (even if it could be improved). As for the script and comedy, it's all fine and enjoyable enough to watch. It's just a shame that it's a romantic comedy. It would be better without the romance, and just being a story about classism and the inequalities created by privilege.