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All You Ever Wanted Was Someone to Take Care of Ya. All You're Ever Losin' is a Little Mascara

By Courtney Enlow | Celebrity | November 16, 2010 |

By Courtney Enlow | Celebrity | November 16, 2010 |

Dear Jessica,

This will not be like my last letter. This will not be like that letter because, against any better judgment and all reasoning, I like you. You seem sweet, your music was fun to sing along to during my belty Broadway phase of ‘99 and you know how to slap your name on cute and inexpensive shoes.

So I say this with all the love and kindness I can muster.

You need to stop being so stupid.

So, so stupid.

This may sound incredibly harsh, particularly to someone I don’t actually know. But when you entered into the bonds of reality television in the wayback of 2003, you opened yourself up to having a million extra friends. And if that hairstylist person won’t tell you, I have to. That’s what friends do.

Your entire career, you’ve been less-than. You emerged in 1999 as a third place runner up to Britney and Christina. Your music career has never been especially good, despite being a more talented singer than the former and more accessible than the latter. You lived as a classic “good girl.” Southern-bred, Christian values, a naive lack of notice regarding the two enormous God-given gifts strapped to your chest, you just seemed like a sweet girl, lost in the shuffle of a career that had no real hope beyond the 98 Degrees of the girl-pop set.

So it made perfect sense when you married the 98 Degrees guy. Nick Lachey, like you, always seemed affable enough. And, at least publicly, he seemed incredibly understanding about your choice to save yourself for marriage, which I would imagine might be difficult for a man nearing 30 in a long term relationship. I assume you must suck like a champ.

A very young 23 when you married, you and your new husband took on the new role of reality television stars in the relatively new celeb-reality market. I guess you figured that your privacy was already out there for the mangling, what with, as happens with sweet naive girls who profess their desire to save themselves for marriage, the whole world knew the exact moment you lost your virginity.

This is approximately the time we as a nation learned about your creepy ass father, Papa Joe.

Joe Simpson, in addition to being father and sayer of the creepiest words ever spoken by a dad not appearing on Law & Order: SVU (“Jessica never tries to be sexy. She just is sexy. She’s got double Ds; you can’t cover those suckers up!” Yes he really said those exact words), is also your manager. And an excellent job he’s done, what with you not being known for your singing since 1999, save for a brief respite in 2005 when you were technically more famous for your newly hot bod, an acting career that crashed and burned harder than January Jones as an SNL host, and your present existence as a human fat joke.

After the divorce, blamed largely on Papa Joe cockblocking your ex-husband at every turn, things went fairly south for you. You were in a movie with Dane Cook, you became best known for being unable to memorize any songs and then perform them live, you did two more movies that did only marginally better than Zzyzx Road, you switched to country, gained 20 pounds, wore stupid jeans, sang at a chili cookoff, then got dropped by your country label.

It then makes sense that you’ve been most well-known for your love life, and sadly painted a spinster at the young age of 30.

You dated John Mayer. That’s a poor decision many women have made, and I can’t totally fault you, because circa “Room for Squares,” sister friend, I’d have been right there with you. We’ve all been stupid. You even dyed your hair brown for him in an effort to appear smarter. Bless you.

That ended in a whimperbang. Then you dated Tony Romo. Mere weeks into the relationship, as you’d done with Mayer, you professed your love publicly, proclaiming him the one. Your creepy ass dad tried to lock that thing up like your vagina before Lachey, and it ended in you being dumped on your birthday before your Barbie-themed birthday.

There’s so much wrong with all the above I can’t get into all of it, but think about it.

Now you’ve been with a “freelance” NFL player (which is what I’m going to start calling myself, too)/business school dropout/divorced man who left his wife for your money you about ten minutes after you met. You’ve been dating for six months. You’ve constantly tweeted kissyface photos of you and saying how lucky you are to be with him, how grateful you are that he loves you, all while he gratefully spends your money.

A couple weeks ago, it was all over the gossip world that you ended up eating at the same restaurant as Lachey and his lady, Vanessa Minillo, and got drunk and started lambasting them to the wait staff. A week later, they announced their engagement. Not even a week later, you announced yours.

If you thought we wouldn’t figure it out, you may have been wrong.

Sweetie, I know you’re not a malicious person. You’re not smart enough to be. And that’s why I know you’re not smart enough to realize that announcing your engagement mere days after your ex announces his is not only a rude thunderstealing move, but makes you look desperate.

For the past few years, you’ve been set into the same category as The Aniston: sad blonde lady can’t hold down a man. And that’s not fair, particularly as you’re so young, But when your entire existence is about the act of “landing a man” then that’s how people see you.

I have long held a theory that fame achieved at a young age leads to an arrested development of sorts, where you remain the same age at which you became famous. In many ways, you’re still a teenage girl. Every man is THE ONE and you pick bad ones. You let daddy run your life and career into the ground because it’s never occurred to you that he’s anything but the best man in the world.

Were you anyone else, I’d be railing against the heinous stupid-cute affectation and weeping for what it’s done to young girls, but in your case, I’m too certain it’s genuine. And that’s okay. Not everyone can be smart, just like not everyone can pull off high-waisted jeans with a too-tight tank at a chili cookoff, and that’s fine. I don’t ask much of you. But I must ask of you this.

Sugar, I want to tell you to take control of your own life, but I worry you can’t. But that doesn’t mean you shouldn’t try. Baby steps. Maybe be single for longer than five minutes. Maybe tell dad you’d like to try out another manager who has actually managed more than a 50-person parish. Maybe you never go near a movie set as long as you live. Maybe you stop telling every thought and feeling to People Magazine.

You’re so sweet and so stupid. If you can’t change that, at least minimize the stupid. Sweet always wins.

Also, that ring is atrocious.

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