The other night I went out for drinks with a couple of friends.

We ended up at Boxers Chelsea—my idea, because of their two-for-one happy hour. We got our first round of drinks (margarita, naturally) and decided to stand outside: It was a little humid out, but much quieter and easier to talk.

About half a drink in, a guy came outside, business-like in a pale pink shirt tucked into navy dress pants, with a gaudy gold chain around his neck. He was cute, the kind of guy that’ll break it down at the club but play it straight during the day with his finance buddies.

He came up to us, cigarette in hand, and I thought he was going to ask for a light. (Which I don’t have: I haven’t smoked since 2008. Regularly, anyway.) Instead, eyes locked on me, he made his way into our circle and lit the cigarette himself.

“I was watching you through the glass,” he said, motioning inside. He sounded a little drunk, but not bad-day-at-the-office drunk. “You’re extremely cute.” He said this right in front of everyone, unashamedly. Everyone looked to me to see how I’d respond.

Not being one for gold chains, and also just not being on the prowl, I showed him a small smile. “Thank you.”

“No, I really mean it. You’re so, like, free, you know?”


“Yeah. You’ve got this whole comfy Dorothy thing going on.”

I looked down at my outfit: a navy silk top from All Saints, a flowy pair of linen pants by Ralph Lauren and my ruby red leather Persian slippers. Casual, maybe… but comfy?!

“That’s my aesthetic,” I nodded, then looked away. He made his way into a corner, finished his cigarette, and we watched him go inside to get his bag and say goodbye to his friends by he pool table.

“He was so into you,” one of my friends said, sucking air through the straw at the bottom of his drink.

“He said I looked comfy,” I spat. “That’s not a compliment.”

“Agreed,” another one of my friends said, “that’s a read.”

“He just said ‘Hey, it looks like you didn’t try when you got out of bed today, and I want you to know I noticed.’”

“I don’t think so,” my first friend shook his head. “Is comfy really that offensive?”

“Yes. I want someone to say, ‘Look at him, that looks so expensive, I bet he didn’t pay his rent so he could buy that.’” Which, let’s be honest, is true.

“Instead you’re out here looking like comfy Dorothy.”

We finished our first round and cashed in our two-for-one cards, and I tried to move the conversation along—but the nickname stuck. “Comfy Dorothy” was on everyone’s tongue—figuratively speaking, of course.

After our second round, I clicked the heels my Persian slippers together three times and went home, vowing to never wear linen pants to a gay bar again.