How Do I Look? Why Women Sometimes Need a Wingman

The other day, as I was driving out of the CVS parking lot, I saw my friend Leigh walking into the store. I waved and slowed the car. She gestured to me like she had something important to talk to me about, so I stopped and rolled down the window. She approached my SUV with purpose.

“Hi! Ohmigod, I’m so glad you’re here!” She said. I wasn’t sure why, but suddenly, so was I! It was great fortune for us to meet up like this! Leigh stepped back from my window and gestured to her legs. “Are these pants too tight on me?”

She was wearing skinny black Capris and a black button down. “No, they are perfect,” I said.

“No, seriously,” she said.

“Seriously!” I answered.

“Like, look again. They aren’t like way too tight?” She turned this way and that. Someone honked and I checked my rearview mirror to make sure I wasn’t blocking traffic.

I tried again. “Seriously. I just saw you walking here, and, in a flash before I recognized you, I thought, there goes a thin woman.”

“No, but seriously.”

“Leigh. You look like what’s-her-name, Audrey Hepburn, in those capris.”

“Because, you know, I’ve recently lost weight, and –“

“I know! You’ve lost a lot of weight. More weight even than you had before.”

“Yes! And so now I have no idea what fits me. Like, I looked at the tag on these pants that I haven’t worn in years and was like, no way an I fit into them, but here I am!” She said, excitedly. But then she reconsidered her potential joy. “Unless they are too tight.”

“Ugh! They are perfect!”

“You need to be a good friend. You would tell me, right? If they looked bad?”

“Yes, I would tell you! Of course I would.”

Notice the interesting shift here. My role in this exchange quickly morphed from fashion advisor/giver of an unbiased opinion to “good friend.” Why was I accused of being a liar and, perhaps, not a good friend? Because of my flattery? If I told her she looked like a fat cow, would I have been deemed an honest, good friend…or a bitchy and jealous wench?

Was there any way to quote-unquote win this, or, at the very least, conclude it and get the hell out of the CVS parking lot in one piece?

Leigh paused. “You aren’t going to put this in your blog, are you?”

I smiled. “Yes, Leigh, I think I am.  Continue reading here.

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