You may be able to sense that I have just the slightest bit of contempt for this film's general concept. As this isn't a review for the movie, I'll try to keep it to a minimum, but before I fully analyze it just let me say, this was one of the films that I liked much better when I was younger (and I'll throw out here for consideration that the first time I saw this, I had no idea what Vivian's profession actually was--I didn't know what a prostitute did; I was in middle school). When you watch Pretty Woman for the guilty pleasure, it's great. When you analyze it from a feminist perspective, or even just a realism perspective, the illusion of perfection falls apart pretty fast.
This joke poster, found on Yahoo Image search, pretty much sums up my feelings about this film.
Can someone reach success or riches through magic/marriage/charm? Well, in short, yes they can. But does it happen like it's shown in Pretty Woman? I don't think so.
Think about other modern-day Cinderella tales. You could argue that Twilight, in which the shy, clumsy, fish-out-of-water Bella Swan marries the rich, handsome, brooding vampire Edward (what is it with that name and romantic heroes?) is a rags-to-riches tale of sorts. Bella isn't exactly impoverished, but compared to the multibillionaire vampire she marries, she's got nothing. But one of the most frequent criticisms of Twilight is how quickly the relationship blossoms. Within a few weeks of meeting each other, Bella and Edward are professing undying love.
That's basically what happens in Pretty Woman. Within the timeframe of a single week, Vivian and Edward have fallen in love. Fallen in love, after exactly seven days. I can't speak for everyone in the world--and I'm certainly not saying that whirlwind romances are unheard of--but I can tell you from experience that it takes me a good few months at least to say for certain that I am in love with someone, as opposed to merely attracted to them or drawn to them, and I know I'm not the only one. My parents dated for several years before they were married. A former roommate of mine texted me six months after meeting her boyfriend complaining that they had only said "the L-word" once. In fact, I was engaged after five months with my now-fiancee and people constantly texted, called, and e-mailed, telling me I was "moving too fast." I wonder what they would say to Vivian and Edward? Something along the lines of "Are you out of your mind," I should think.
I understand that this is a movie, a romantic comedy, and shouldn't be taken as an accurate portrayal of real life. And I understand that when comparing this to its fairy-tale roots, you could argue that "Cinderella" does the same thing, but what sets that apart is that it was written down and published several centuries ago. Back then, arranged marriages in western countries were common, and it wasn't remotely unusual for women to try to "marry up" in order to secure better situations for themselves or their families, nor was it uncommon for them to take the first offer they got to escape a less-than-pleasant situation or just to escape being lonely (think Pride and Prejudice, or Jane Eyre). Back then, only knowing your intended for a few days--or seeing them for the first time on your wedding day--wasn't exactly a unique experience.
But this movie was made in the 1990s, and arranged marriages are no longer the norm in most Western cultures...and while Vivian and Edward don't marry on-screen, it's implied that they will in the near future. By securing herself a future with a rich, socially advanced man, Vivian eliminates the need for the G.E.D. she was planning to get. If she so desired, she could use a bit of her soon-to-be husband's money to provide for her former roommate. She can have anything she wants now, and all because she's captured the attention of a wealthy "handsome prince."
Vivian admits to her desire for a "fairy tale," but frames it as a desire for love rather than a desire for money. In written tales like "Cinderella" and "Donkeyskin," love plays a big part of the decision to marry--but it's always based on first impression, and beauty usually plays a huge part in it. If Donkeyskin, Juleidah, Catskin, Cinderella, and of course Vivian weren't all classically beautiful, it's doubtful they'd have captured their beloveds' hearts so easily.
Basically, what I find so insulting about the rags-to-riches element of Pretty Woman is this: it makes prostitution look about 1/10th as dangerous as it really is, makes light of prostitution, drug rings, dangerous living situations, childhood abuse, and unhealthy relationships...and then pulls around and says, Don't worry, though--if your life sucks, find a rich man and make him fall in love with you, then make him prove it. You'll get everything you want in the end.
This isn't to say that the feminist element is entirely lacking. Both Cinderella and Vivian have their moments. Vivian is certainly the sassier, more proactive of the two, but in the 90s it's a bit more socially acceptable for women to show independence than it was back in the Grimm brothers' day.