I recently rewatched this movie after having a disagreement with a friend over whether or not this movie has merit. We'll get to that.
The Set Up
Get ready for stereotypes galore. The Big Bad Boy, Tank Turner (Dane Cook), is the worst first date ever...on purpose. He's hired out by men with the sole purpose of sabotage in order to send girls running back to their exes. He also is best friends with Just a Friend, Dustin (Jason Biggs), who goes over the top and out of his way for Stereotypical Good Girl (Kate Hudson). This includes doing activities he wouldn't do in order to get her to fall for him. For some reason, being on the verge of playing “Every Breathe You Take” in the bushes by the Police, just isn't getting her, so he requests his friend to send her running into his arms.
Part of the problem for Dustin is that he is scaring the living daylights out of Alexis who even coins herself as a “serial monogomist.” Her best friend (Lizzy Caplan, The Class and Mean Girls) tells her that she clearly needs to date the anti-Dustin to move away from his over the top “I love you's.” So Tank's attempts to ditch her fail.
The characters are played appropriately by Dane Cook and Jason Biggs. I probably would've picked a different actress than Kate Hudson for the Good Girl, but that aside, she did a great job. I see her more as the bitchy chick from Bride Wars or Something Borrowed. Unless she's in Almost Famous, and then she's paramount. Moving on...
Tank's ditch efforts are over the top, hilarious, and downright awful. He's a vulgar jerk who enjoys his shitty job and is even proud of his job on the side where he makes girls' ovaries curdle. The film is mean spirited, but the end result is shock, horror, and in my case, howling laughter.
Yet, it Does Happen
The truth is, a lot of girls date guys who are terrible for them. Yet, here's the thing: they break up and go out with someone new and (sorry Tank) sometimes, even if it is a good date, they realize how easy and familiar being miserable is. Not consciously, of course. Dating new people and being optimistic about the uncertain future is hard for people, and the past, no matter how bad, can prove hard to get away from. It is so easy to slip into old habits. To make yourself believe that something can work and you can be happy. That is something this movie demonstrates shockingly well.
Another truth is that people do buy into stereotypes, even the ones about themselves. Tank Turner doesn't let himself be the good guy, because he believes people when they tell him that he is an abysmal excuse for a human being. Because he's so good at helping buddies and clients get their women back by being a woman's worst nightmare, he comes to the conclusion that he can't be anything else and isn't any more than what he's reminded.
He also deeply cares about his best friend, Dustin. In order to make things right with the woman he loves and his best friend, he decides to sabotage himself. He could pick a better time and place to sure, but it wouldn't be half as funny. This is the least realistic part of the movie, but by far the one that comes to mind whenever I consider what film to reacquiant myself with.
Another message of the film is that not only can bad guys be good guys in disguise (an unfortunate stereotype used over the top by Hollywood—see corresponding Cracked article) but that good guys can be bad guys. Not every nice looking guy is truly nice. One of Tank's clients sucks up to his girl and her family while he cheats, lies, and ruins his girlfriend's life. Men like that can keep an act going on for years, which is part of what Tank realizes during the movie. He may be doing the guys a favor, but he's doing women everywhere a diservice by allowing them to run back to their malnurished emotional life, because that could be as good as it gets. Maybe even short changing the woman he falls for on a man she deserves.
The last lesson is that although gentlemen often believe that “nice guys finish last,” a more adequate response would be that they are pulling a Nice Guy by declaring their love too soon, being something they're not to win her, and being her best friend in the world in order to get a date. Women see this like men see desperate women—by smelling them a mile away. They don't buy it. I disagree with the movie that all women want bad boys, but I do agree that especially in this culture, being an asshat can win a few confidence points and that tips the scales in a negative direction. Moral of the story? Don't be an asshat and don't be the pushover.
I like this film. I take it for what it is, but it's also more than just another rom com. It is wash your mouth out with soap vulgar and uncomfortably true at others. If you are sensitive to men treating women badly and those women taking it, you probably shouldn't watch it. If, however, you identify with any of the above mentioned paragraphs, it is worth a try. Or you can just count the times you laugh at the worst date you didn't go on.