Fast forward to 00:48 and enjoy.

There are few things on this planet more chic than a beautifully dressed woman of a certain age. It’s not just chic, it’s sexy. It’s the woman who knows exactly who she is and what she wants (and trust me buddy, if you won’t give it to her, she’ll either find someone who can or get the damn thing for herself) and I just cringe in envy every time I see one because no matter how smooth my forehead or perky my…attitude, there is just no competing with that type of gorgeous, powerful, sexy woman.

So why am I seeing so many otherwise beautiful women in their 40′s and beyond –who could look so fantastic in age-appropriate clothes– all shot to hell with the bo’ and traipsing around like drunken goats in absolutely tragifying (what? it is so a word. Language is fluid, yo.) outfits better left to either their teenage daughters or, in the best of all possible worlds, some sort of Barbie Dream Bonfire.

Why is that?

I know there is a great premium put on youth and women are constantly getting messages like “men ripen, women rot” (can’t tell you how charming I find that one. Seriously, it’s right up there with that “If you can read this the bitch fell off” t-shirt sported by so many of the less bathed bikers I see) but, if you are a woman of a certain age, are you sure you’re dressing for the position you’ve earned? Trends are fine, but at some point they should be replaced by personal style.

The time for super short skits, yes, even when paired with opaque tights, is your 20′s. When you’re a child, you talk as a child, you flirt as a child and you dress as a child. When you’re a cougar you put away childish things and buy yourself some darn Prada.

You know the drill: I post a pic, you send me your best captions, we all have a good laugh, and I declare a winner next saturday. Have fun!

Meet Plumcake in the bar of her very favorite southern grand hotel, The historic Jefferson Hotel in downtown Richmond. Cocktailing starts at 5:30!

In Beautiful Washington D.C., home of many important events in our fine nation’s history, including Plumcake’s birth! Details forthcoming! Who’s gonna be there?

Two more cities will be announced in the coming days! 

So, I’m sitting here at my favorite lounge drinking Tanqueray 10 and eating a brownie the size of my skull, reminiscing about childhood (must be the heady combo of booze and baked goods) and thinking about my love affair with chocolate.

Just like there is a vast difference between lovin’ and good lovin’, there is also a vast difference between chocolate and good chocolate and –not unlike the aforementioned good lovin’– it is readily available on the open market from the talented and enterprising French…if you’ve got the cash.

Case in point: this beyond delicious “luxury box” of French chocolates. My friends, this is the cocoa buttery equivalent of being trapped on a desert island with the entire heterosexual contingency of the Oxford AND Cambridge rowing teams (and really, two guys on a desert island ought to be plenty for anybody) and an endless supply of hypoallergenic baby oil.

The holiday pack from Zchocolat is possibly the most luxe take on the traditional box-o-chocolates I’ve ever had the good fortune to stumble across.

Check out their chocolate list here but beware…you’ll probably need a cigarette afterwards, or at least a shower.

The first city for the Manolo Big Girls Face to Face will be announced tomorrow!

If you want to cast a vote for your city, be sure to comment. If a city gets enough votes, we’ll try to work it in to this or subsequent tours.