Ronald Miller (Patrick Dempsey) is a high school nerd who manages to convince Cindy Mancini (Amanda Peterson) to prostitute herself to him for a month, but never once manages to get laid out of the situation. Someone's doing it wrong.
Ronald has been watching Cindy for a long time, but, as the story goes, she's the beautiful captain of the cheer leading squad, and he's the mower of the neighbourhood's lawns. While her friends rule the school with their popularity, he and his friends are the polar opposite, going as far as to sit in the visiting section when they attend their school's football games.
While Ronald claims that they were all friends back in the day, Cindy can't even remember his name, referring to him as Donald on more than one occasion. Even though they live across the street, and he's stalking her, their paths seem destined not to meet until Cindy ruins an expensive jacket belonging to her mother, and Ronald offers to pay for it...in exchange for her services.
In the beginning of the film, Ronald just seems like a dopey, love-sick geek who'll do anything to get the attention of the popular girl living across the street. In contrast, Cindy starts the movie as a vapid, spoiled brat who puts more focus on her wardrobe than she does on anything else. These roles are quickly reversed (within the first twenty-four hours of their fake relationship) and Cindy quickly grows to be a caring and loving individual while Ronald turns into quite the douche-bag.
Actually, Ronald rubbed me the wrong way from the get-go, but more so after he walked up to Cindy and, point-blank, asked if he could "rent" her. Cindy was, naturally, repulsed by the idea, but really needed to be saved from her situation, and reluctantly agreed to help him out. We were lead to believe that she was the villainous one in this pairing, as she ignored him to the point that she thought his name was Donald, but, I mean, really.
The agreement that they come to is that Ronald will pay Cindy $1000 if she pretends to date him for a month, but there is to be no hand-holding, no kissing, and he's only allowed to sit with her at lunch four times a week (which is actually quite a lot, in my opinion), but Cindy is forced to keep things a secret or else risk exposing Ronald's sleaziness to the entire school.
In the most brief makeover I've seen, Cindy takes away his hat, glasses, styles his hair (because, you know, all teenage girls have hair gel at the ready), rips the sleeves off of his shirt, and pops his collar. LOOK AT THAT, PATRICK DEMPSEY'S ATTRACTIVE! WHO KNEW?
The only trouble that the pair run into is when Ronald, now Ronnie, first goes to sit with Cindy at lunch, and the jocks tell him to leave. Cindy sticks up for him, as she's paid to do, and, suddenly, everyone's okay with Ronnie. So he's popular now, or, as one of Cindy's friends describes, "he went...from totally geek...to totally chic."
Within the month that the two of them are dating, Ronald goes from being so timid that he allows himself to go hungry while Cindy's friends eat his lunch, to being the big man on campus who uses one of the poem's that Cindy's written to score with another girl. Cindy's written in a way that she could be two separate characters: the shallow Cindy dies within the first twenty minutes of the film and is replaced by the empathetic Cindy who doesn't seem to mind hanging out with Ronald. It's as though the writers couldn't think of how best to transition her into a better person, so they just did it off-screen.
Ronald and Cindy become very good friends over their month together; Cindy shares with Ronald her poetry, which no one else knows about, and Ronald insists that she could do anything she wanted if she actually tried. He counsels her about her boyfriend, takes her stargazing, and is such a great guy that she actually falls in love with him, but when she leans in for the kiss, he asks about how they're going to break up their fake relationship.
It's during their fake fight that the two of them show their true colours; Cindy wants to do it privately and just tell their friends that things didn't work out...Ronald wants to scream at her in public, letting everyone know that she's the one being broken up with, and slings insults at her. Cindy's advice to Ronald: "stay yourself. Don't change to please them," is a lot nicer than whatever I would have said to him. Ronald eventually tells Cindy off for ignoring him for sixteen years, as though that justifies his behaviour towards her.
Now that Ronald's part of the popular crowd, and single again, he starts dating all of Cindy's friends while she looks on dejectedly, and even helps his new found jock friends throw feces at the house of one of his own (former) friends, Kenneth. He later wonders why Kenneth won't accept his apology, which leads to my favourite line "YOU SHIT ON MY HOUSE! ...you shit...on my house..."
When Cindy's college boyfriend breaks up with her for prostituting herself to Ronald, she reveals to everyone that she was paid to pretend she liked him, causing him to be shunned by all of his new found friends and growing into the biggest social pariah at the school. Even so, Cindy continues to defend him when her friends mock him and seems to have genuinely fallen for him.
Ronald only regains the respect of his peers when he stands up for Kenneth when he gets into a skirmish with one of the jocks. Because that erases all of the horrible things he did. At least it does in Cindy's eyes, because she goes running back to him.
I don't imagine that the two of them would make it very long as a couple, but I can see one of two possibilities for their future:
In the first, and I suppose optimistic, version of things, Ronald and Cindy would become the power-couple of the school. Ronald, having learned his lesson and grown humbled from his experiences, would become a much better person and give Cindy the attention and respect that she's earned. Cindy would no longer allow Ronald to get away with any of his bull crap, and the two would play off of one another very well, having both hurt, and been hurt, by each other in the past.
On the other hand, what I think is far more likely, is that the two of them will have a few good months together, and then fall back into the same pattern where Ronald grows to be somewhat abusive. I'm not saying he would hit her or anything, it's more likely that he would abuse her emotionally rather than physically, but it's still not a healthy relationship for the two of them to be in.
I think Cindy needs to just be alone for a while, or maybe try being just friends with Ronald for a while to see if he can resist growing into such a jerk off in the future.
What bothers me most about this movie is that, in the beginning, Ronald is saving up for a telescope, and he spends the money instead on buying Cindy's attention. As much as I appreciate watching the two of them speed off on the lawnmower at the end, I would much rather see something relating to them stargazing through his old telescope, as that's the date that he took her on earlier in the film.
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