Pajamas on a First Date (and Other Oddities of Long Distance Courtship)
By Kimberly Dark
Some people will pick any reason not to get a good night’s sleep.

“I thought the pajamas meant you didn’t want to have sex,” she said. “But then, you’re rubbing up against me the moment we’re in bed. I thought, what does this woman want?”
I assumed I was being so clear, pressing against her thigh, tracing her tattoos with my fingers, kissing her neck and sucking her fingers. Nope. Not clear at all.
“I thought you were just being friendly, you know, acting cuddly.” She looked at me like I was deliberately trying to confuse her — again.
“Oh, honey, when I’m just being friendly, I don’t generally use that much tongue.” I replied, flirtatious, though wide-eyed at her confusion.
I’m not usually the one to make the first move, but I know how to work a come-on, know how to set myself up for the first move. In the book of romance, I pen the pages with the little roman numerals — I leave chapter one up to her. In this particular case, I had done quite a bit of first-move prefacing. The whole thing was a bit awkward. We thought too much of our abilities, as people are prone to do in this jet-setting age. We met in one country, flew back to our respective countries and then next time I was in her area, we set the date. We were destined to be lovers on that first day because of how things heated up via email after that first meeting. It’s as though the first date had to be a sleepover. Okay, it wasn’t just a sleepover; it was a week of sleepovers. What were we thinking? It was night six before she finally said something about the pajamas I’d been wearing.
“I started thinking you got off on me taking you despite your unavailability.” In her mind, I was making a silent pajama protest.
I don’t sleep well in a frilly thong panty. It’s good to have that lesson behind me and move on. A silky nightgown with spaghetti straps can be nice for sleeping on a warm night. Heavier, longer gowns just seem oppressive. Who wants to spend the whole night dreaming you’re Jane Eyre walking the moor against a strong wind thwarted by a heavy fabric around the legs?
I used to sleep in a t-shirt and panties — that was the fashion for slumber parties back in the 70s. I once had a lover who thought my sexiest lingerie was a man’s undershirt and boxers. It was the contrast, apparently — the way the curve of my body refused to look manly, even in that attire.
I’m something of a sleep connoisseur. I’m a cuddler, no doubt, but only when falling asleep. Once I’m asleep I’d rather not be touched too much. It might wake me up, or interfere with dreaming. I’m busy; don’t mess with me. That always offended my ex. “Oh yeah, you’re all cuddly in the beginning, but after the first little snore, it’s everyone to their corners!”
“I’m something of a sleep connoisseur.” — Tweet this.
I was still puzzling over the weird experience with the woman who couldn’t see a come-on coming. I was carrying it through my days like a purse that doesn’t match my outfit, opening the issue in my mind and rifling through the contents, dissatisfied. Luckily, I met a fellow pajama ponderer who gave me her expert opinion.
“She thought it was strange that you were wearing pajamas, but that you were open to love-making?” She summarized after my brief explanation.
“Yeah,” I said, looking for insight. “Aren’t there times when you wear pajamas to bed, but you’re still open to sex?”
“Oh sure. There are great reasons to wear pajamas to bed with a lover” my friend replied over cocktails. Well, she wasn’t a close friend, more of a cocktail-friend. Okay, we’d just met, but when the topic of pajamas came up in conversation, I simply had to get an outside view. She began to expound on the various ways in which one might come to wear pajamas to bed with a lover. I marveled at how well she’d thought this through. It was as though she’d been waiting for just this opportunity to discuss pajamas with a near stranger. I was both fascinated by her articulateness and grateful for her clarity.
“Okay, so the pajama question might not come up with a lover at all. Like, if you’re making out on the sofa and getting all up under each others clothes, you’d just move the whole party to the bedroom at some point, right? I mean, you’d just take off the clothes off as you went and by the time you arrived in the bed, bam! You’d be naked and you’d be all over each other and so, how would pajamas even get involved?”
“They wouldn’t.” I replied simply, shaking my head for emphasis.
“Right. They wouldn’t. But let’s say you weren’t getting romantic on the sofa. Let’s say you were just on your way to brush your teeth, get ready for bed. There’s a certain getting ready that requires being clothed. Most people don’t brush their teeth in the nude. Well, at least not in someone else’s home. At least not with someone else around. I mean, you’ve got to be pretty intimate to brush your teeth in the buff in front of someone,” she said.
“You’ve got to be pretty intimate to brush your teeth in the buff in front of someone.” — Tweet this.
“Right.” I frowned a bit, considering naked tooth brushing in the company of a new lover. “No, that wouldn’t occur to me, unless the tooth brushing happened after the first episode of love-making,” I added. “Then maybe I’d just carry on being naked. There’s already an intimacy there.”
“Exactly,” she said squinting a bit at me, drawing out the word as though we were deeply understanding one another.
The real problem with that lover was lack of intimacy. She saw those pajamas as an impenetrable fortress because she had to focus her anxiety somewhere. I pondered this during the conversation, but I didn’t share with the pajama-master before me. We had never made out on the sofa and then moved it to the bed and that disturbed me, somehow. She had never kissed me — not even a peck — outside of bed. I found that peculiar. We were lovers after all — strange as the whole thing was becoming. Why couldn’t we kiss, be affectionate? Or maybe even do something radical, like hold hands. There was plenty of kissing going on in bed — kissing in all regions. Just never out of bed.
During the first day or two of that visit, I walked up behind her as she gazed out the window. I slowly touched her shoulders, moved my face in toward her neck and kissed her gently. We were already lovers and I was just being… tender.
She didn’t speak at first, but the vibe felt as though I’d just walked up to a stranger on the subway and kissed her neck. I wasn’t sure if I should fear being slapped. Very puzzling. Were the pajamas still to blame for confusion in that incident too?
Even after all the pondering, I stand by my fondness for pajamas. I went through a period of nude sleeping in my youth. And I still sleep nude if I fall asleep right after sex. That’s easy sleep: orgasms prompt a hard fall into slumber. It’s a sleep where nothing matters: a poorly placed elbow, sweaty skin, wet spots in the bed — who cares? The body just lets go. Nowadays though, if it’s not post-coital sleep, nudity doesn’t suit me. Light cotton pajamas primarily, and roomy, so I maintain a full range of motion in the legs. It’s subtle, the sleep enhancement provided by pajamas. Nude is fine, but sometimes vulnerable in the dream time. I mean, could you do kung fu in those pajamas? Okay, you may not know kung fu, but in a dream, you’d know it if you needed to. In the nude though? I don’t know about that.
My drinking buddy continued her thesis on pajamas. “Yes, you definitely need pajamas — or a robe — so you can get from the bathroom to the bedroom without seeming like a nudist. And if you were traveling, I’ll bet you didn’t have a robe with you, did you?” I shook my head no. “Right. So, you’d have been wearing pajamas. So, were these big heavy flannel pajamas — or something lighter, more inviting?”
I thought back to the pajamas — the only ones I had with me: pink cotton bottoms with little kittens on them. Not fluffy cute kittens, black, big-eyed winking kittens with curly tails. Sexy, in a girlish kind of way — that’s to my thinking at least. And on top, a tight pink lace see-through spaghetti strap tank top. I explained this to pajama-friend and added, “Isn’t a glimpse of nipple still considered a come-on?”
“Definitely.” She said, and swigged her vodka tonic. “I think she was a little thick. I mean, look, someone like you wouldn’t want to assume there was going to be sex involved and just get naked, you’d set up a come on. You’d make an invitation.”
What she knew about someone like me had all transpired within the last two hours, but actually, she wasn’t doing too badly with her divination. I nodded and said, “Yeah, that’s what I’ve been thinking. The pajamas, the alleged “cultural” misunderstandings — all symptoms of a lack of intimacy, fear. I still don’t understand why she was so afraid of me.” I added.
My companion shrugged. “You’re a little scary.” She said.
“I pick women who can handle me,” I said plainly. I raised an eyebrow at the incoming memory “and wow, she handled me pretty well, but only once the lights were out, pajamas off. Until then, it was a mess.”
“Live and learn,” said my companion wisely. “Don’t torture yourself over it.”
Grateful for the wisdom of this advice, a few cocktails and the advancing evening, I hugged my new friend and headed home to my pajamas. Of course that relationship had not lasted — anywhere but in my own head— so why not let it go? Indeed, some people will pick any reason not to get a good night’s sleep.
Kimberly Dark is a writer, sociologist and raconteur working to reveal the hidden architecture of everyday life, one clever story, poem and essay at a time. Learn more at www.kimberlydark.com