Advice from the Prettiest Girl in the Office, by Grace Bello

Dear Prettiest Girl in the Office,

Unlike me, my friends have full-time jobs. When they invite me out, we always go to clubs that serve $14 martinis. I try to say no, but I don’t want to rock the boat or seem cheap. What do I do?


Funemployed in Fresno

Dear Funemployed,

I understand what you’re going through. When I first started modeling as a fresh-faced teenager, I worked as a cocktail waitress at one of those kinds of places. It was full of handsome, rich men in suits. You know, like in the movies?

A lot of those guys were super generous. Eventually, they weren’t so much buying drinks for their girlfriends; they were just buying drinks for me. Once, a man tipped me $100 without even ordering anything!

Come to think about it, making enough money to go out isn’t so hard, don’t you think? You just have to put your mind to it and be able to stomach a lot of roofies.

This legal secretary gig I’ve got now? I didn’t have to, like, apply, or whatever. My boyfriend Julian got it for me. He’s a partner at the law firm. The job is just temporary until he proposes to me. Then I won’t have to see the inside of an office building ever again. Well, except when I finally start that charity in my name that helps homeless teens look more attractive.

Long story short, Funemployed, keep plugging away, maintain an open mind, and always look “available.”


The Prettiest Girl in the Office

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Dear Prettiest Girl in the Office,

My in-laws moved in with my husband and me to help take care of our newborn son, but they’re driving me crazy with their nagging! In light of their generosity, would it be rude to ask them to give me some space?


Wiped Out in White Plains

Dear Wiped Out,

Ah, in-laws. I’ve never had them, but I will soon!

You know what? As I’m in my cubicle typing this, something occurs to me. I feel like the only way to really get to know the world is to work for just a few years. I mean, how else would I have won the heart of one of the most eligible bachelors in the city? Once we’re married, transcribing clients’ voice mails will be a thing of the past! I’ll hand in my resignation the second I see that blue Tiffany box. My hardest problem after that will be making sure not to drink too much while I’m relaxing by the pool all day.

Oh listen to me, Wiped Out…I know this all probably sounds like a fairy tale compared to your life!

Julian says it’s only a matter of time until his wife signs the divorce papers. And why shouldn’t she? She must know that she’s not satisfying him sexually. Obviously, I’m the one he really loves. He hasn’t said it in so many words yet, Wiped Out, but he’s implied it. Sure, his wife may be the one who went to “college,” put him through law school, and birthed those ugly twins of his. But I’m the one who was in a national TV commercial co-starring MTV’s Dan Cortese.

And I give better head.

He’ll ask me to marry him any day now, don’t you think? A month ago, he took me out in public for the first time. Sure, it was at a dimly lit restaurant and he was wearing sunglasses, but still! And this morning, he asked me to text him a naughty picture of myself. You don’t ask that of just anyone. Right?


The Prettiest Girl in the Office

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Dear Prettiest Girl in the Office,

I’m a college sophomore. I have a huge crush on my RA, and once a week I find some excuse to “run into” her at her part-time job at The Strand. The problem is, we’re friends and I’m scared she’ll never think of me as anything more. How do I tell her how I feel without risking our friendship?


Horny in Harlem

Dear Horny,

Hello? How selfish of you to ask me about your random problems! Can’t you see that I’m going through something really serious here? I’m trying to land a husband, and you’re sitting there asking me how to hook up with some chick who is clearly out of your league. What do I fucking care about your crush on your RA?

I don’t even know what the hell an RA is!

Let me tell you something, Alone. At least you’re still young! You know what happens when you get older? You get crow’s feet, no one cards you anymore, and maybe every now and then you get a modeling gig for a sewing pattern or the GOP website. The other day, some kid at Starbucks told me I was “the hottest cougar he’d ever seen.” Cougar? I’m young enough to be his sexy cousin from out of town!

What the hell is Julian still doing with that crater-faced cow anyway? Is he afraid he’ll lose the ranch-style house in Connecticut? Is he so attached to those ADD-addled ginger kids that he calls his children? That idiot. For Christ’s sake, I was the face of Teen Kleenex, the first and only Kleenex for teens!

Alone, do you have a car? How soon can you get to Brooklyn? I need a Cosmo, and I sure as hell ain’t drinking it alone.


The Prettiest Girl in the Office

Grace Bello is a New York-based writer. Her work has appeared in USA Today’s Pop Candy, McSweeney’s, Flavorpill, Bookslut, and more. Follow her on Twitter or in real life.

The Humor Section features a piece of original humor writing each week. To submit to it, send an email to Becca O’Neal.

Advice from the Prettiest Girl in the Office, by Grace […]