Cosmo web assistant Leo (Smith '07) has been instructed by her "26 year old Cosmo pro" of a boss to blog for thirty days about the struggle of "one socially awkward girl attempt[ing] to transform into a sexy, social butterfly." Young Leo is like Angela Chase of Cosmo: earnest and endearing and totally non-evil, which is obviously holding her back in the fashion world. (Her roommate puts on her eyeliner for her in the morning 'cause she doesn't know how! Aw!) Increasingly, watching her thirty-day evolution at the hands of people who professionally suggest "how to be a total man-magnet" is like watching a gazelle getting torn apart by hyenas.

Writes Leo in her introductory post:

My boss, Christie, took one confused look at me and said, "Leo, I am going to tell you something. You work at Cosmo now. And that means that you always have to bring your A-game. You've got to learn to fake it until you make it, and you might want to consider knowing how to flirt as part of your job description. It's time to Cosmo-up.

No. Don't. Seriously, don't. We just want to tell her that she's just perfect the way she is!

We get to hear about her painfully bad first dates—which apparently, people still go on?—which leave her so shaken that she starts writing things like:

The first thing I did when I got to work was read the last month's worth of conversation starters we've run on Cosmopolitan.com. If I'm ever going to avoid a repeat of last night, I should probably stop my current Google habits. My browser's history showed me that I have an avid interest in Tibetan singing bowls, foot surgery, the Chunnel, Marky Mark and "lose 10 pounds fast."

I need to start thinking sexy thoughts if I'm ever going to become the seductress I'm aiming to be.

No - noooooo! Do NOT listen to Cosmo! Her readers are totally unhelpful, making comments like, "Get some amazingly hot panties and I guarantee you'll feel a little bit more sexy."

Sometimes she goes to a party she doesn't really want to go to and a fairly douchey guy gives her his card, or she gets the phone number of an equally sweet Mr. Montana at a Cosmo party.

As of yesterday, things are going way better for her now:

I must be doing something right, because Helen Gurley Brown, the Cosmo Queen herself, likes my shoes.

Hang in there, Leo. We'll be watching and rooting for you.