Does This Stranger Make Me Look Fat?

Last Thursday, I spent the whole morning nearly buck-naked with a perfect stranger. And it wasn’t by accident. In early May, as Mother’s Day approached, I said to my husband, “Please don’t send me flowers. If you’re going to spend money on me for Mother’s Day, buy me a session with Jennifer.”

This was a big step for me on many levels. The first being Asking For What I Want, and not because I’m depleted and at the end of my rope, but just because I might enjoy it.

The second was Asking For Help, specifically for something other than killing a bug or plunging a toilet.

And finally, of course, the naked thing.

Jennifer is a wardrobe consultant and I was about to try on for her everything in my closet.

People who know me – who know how infrequently I leave my house – are puzzled that I’d even need such a service. “Did you tell her you were looking for some Downstairs Outfits?” one friend joked.

But this idea came about because I had a meeting to go to a few weeks ago and I nearly cancelled because I didn’t have anything to wear. I don’t mean, “Oh, I don’t have a thing to wear.” I mean, literally, I had a skirt and no top that matched. It’s been a long time since I’ve gone shopping, but I couldn’t believe I’d let things go this far.

Years ago, when I worked as a bartender, I remember sharing with a few of the “regulars” that I was about to start therapy. “You’re going to pay someone to listen to you talk about your problems?” they said. “Don’t you have any friends that will do that for you?” That exchange echoed in my head when I made my initial request to my husband. I have many fashionable friends. Why not just ask one of them to go through my closet with me?

But there’s something about cleaning out your closet with a total stranger that feels a little reckless – a little more dangerous than with a friend, tried and true. My friends are not going to force me to get rid of the skinny jeans that I wore exactly twice but I now can’t button, because I’m going to tell them that I’ll get back into those jeans one day and they’ll humor me because they love me. A stranger won’t do that. That’s the beauty of strangers; you never know what they’ll do.

I told Jennifer about my cranky feet and how I have to start an outfit with whatever shoes I’ll be able to tolerate that day and work my way up from there. I explained that I’m not very fancy, but I want to look more put together.

“I get it,” she said. “You want to look good, but not like you’re trying too hard.”

Yes, I told her, because right now I look like I don’t try, ever, at all.

She explained what we would do for the next few hours. We’d go through everything in my closet, make outfits, toss whatever looks awful and then she’d make suggestions about what I should pick up to round out my wardrobe. “Do we need coffee for this?” I asked. “Or wine? Or Xanax?”

We ended up needing none of the above and the process itself was the most fun I’ve had with my clothes on. (That was cheap, I know, but I couldn’t help myself.) Jennifer has a keen eye and is a master of diplomacy. She cheerfully rebranded all my Grateful Dead clothes “Bohemian” and let me put them back in the closet.

Even so, in no time at all I slid comfortably into my role as the naysayer. “I can’t wear that! I look too hippy. I’ll be too cold. Too much skin.” But she took me by the hand and forced me to look at myself with new eyes, and by the end of the first session, I had a dozen new outfits to wear – things I never would have put together myself – and I already owned them all!

But it wasn’t just the outfits that made me giddy. There I was, doing something I probably shouldn’t have been doing, with someone I don’t even know, and once I got used to unfamiliar hands reaching around me to clasp necklaces and smooth pleats, I couldn’t help thinking, Girlfriends, we should all be spending our mornings naked with strangers.