I’ve pretty much left you alone—despite your car crashes, shots of your delicate, powder-filled nostrils and your lesbian “relationship.” See, despite all these things, I have to tell you, I like ya. “Mean Girls” was a good flick, and dammit, if you can’t be cute and charming and all that shit. And unlike the other dreck from your generation—who did you used to feud with? Hilary Duff? Paris Hilton?—you got personality. I was always rooting for you, Lindsay, always. When you would text one of their mans, throw a vodka and Redbull at them or, well, fuck one of their mans, remember, I was all like, “Oh, that Lindsay. Just young and stupid and having fun!”
Anyway, as a former bad girl, I hope to give you some advice on surviving the clinker with your clit intact. Though I have never been to jail personally—let’s just say that I’ve been real lucky at evading the police—I feel like I wouldn’t be the worst at it. Probably not the best, either, but hey, unless you’re a 350-pound butch lesbian named Level 3, you’re probably not gonna be the best at prison no matter what. But I am fairly certain that I would be average, if not slightly above average, at prison. And so, I want to help you through your ordeal.
First up, no more tears. I know, I know, it’s tough when life is unfair, and that mean judge is looking you up and down and tells you that you’re gonna spend 90 days in the pound. I mean, women are getting stoned to death in Iran, for fuck’s sake, and you need to Twitter about it. But tears ain’t gonna get you nothing but pounded—and not in a good way. Tears to prison bitches is like blood to sharks. Just a few drops and you got a feeding frenzy going on. Use those “acting” skills you’ve developed over the years in such fine performances as “Freaky Friday,” “Herbie Fully Loaded” and “Labor Pains” to avoid such a situation.
Also, pretending like you’re pregnant a la “Labor Pains” may get you some leniency. Or something. Whip that pregnant suit out.
Get those hair extensions out of your scalp. Pronto. When engaged in a catfight, a woman’s hair becomes a huge detriment. You need only watch “Rock of Love” to witness this fact.
Get rid of those nails while you’re at it. When someone is punching you in the face with your own hand, you don’t want sharp little weapons attached.
Make sure that your folks on the outside are well versed in what they will have to smuggle into prison. Cigarettes, iPhones, tubes of KY for fisting—if that means nightly seminars on inserting things into uncomfortable places, then so be it. Mommy Dina should be able to get everyone up to speed on this.
But, cheer up, Lilo. You can make friends on the inside. In fact, this is probably going to be one of the most profound experiences of your entire life. Think about the street cred it will give you. No method class will have anything over you—you lived it! And, if you play your cards right, you can find someone who might just beat the crap out of your pops, Michael, once they get out. Probably for a pack of smokes too. Prison. What a bargain!
Love and kisses,
P.S. Also, there’s no way you’re gonna do the full 90 days. Paris was sentenced to 45 and only did 23. I mean, you’ll do like 30. Tops. You’ve had benders that’ve lasted longer than that.