“What do a penis and a Rubik's Cube have in common?” my grandmother asked my new boyfriend on our visit to her nursing home. “The longer you play with them, the harder they get,” she said, before erupting into hilarious laughter. 

Tony shot me a glance as if to ask for permission to laugh. I smirked and nodded my head toward her bookshelf to draw his attention to her collection: 1001 Dirty Jokes sat comfortably beside a book of crossword puzzles and a copy of 50 Shades of Grey. I had grown used to Nanny’s sex jokes, but that didn’t make them any more comfortable. 

’ve always had a complicated relationship with sex. Before Tony showed up, I was a 33-year- old virgin who rested comfortably in the idea that my body wasn’t anything worthy of carnal desire, but rather it was merely a large fleshy vehicle required for carrying around the only thing I felt confident about, my brain. Tony was lightning in a bottle, so when the bottle broke three years in at the precipice of the pandemic this year, I crawled back inside my brain and readied myself for the inevitable drought to come. 

Growing up as a strict Catholic in the Midwest, my family never talked about sex. The only window I had into such matters were hours of unsupervised MTV and raunchy jokes Nanny would tell regardless of the occasion. At 13, she single-handedly won over all my friends with a speedo-stuffing joke told at my Catholic Confirmation party. No one else had a sexy, chain-smoking, vodka-sipping, grandma. But while my friends were in awe, it was clear my parents had a different take. 

Nanny wasn’t a serious woman, with her leopard-print blouses and Elizabeth Taylor hair, and if I wanted to be taken seriously in the world, I should focus more on my studies and less on attracting a guy. As far as I could tell, they weren’t wrong. The world was easier to process in a binary sea of 1’s and 0’s and my operating system simply wasn’t programmed for sex. I also wasn’t particularly close to Nanny and after I moved away, our interactions were scarce. 

Despite that, when she moved into the nursing home, she gifted me with one of her few prized possessions, a painting she had purchased from a local gallery in the ‘70s. This large painting of a voluptuous Spanish flamenco dancer mid-twirl — after hanging in every smoke-filled apartment I ever remember visiting her in — now hung proudly in the center of my home. During the last years of her life, I made a point to stop by the nursing home, hear her favorite joke of the day, and watch her boss the nurses around. 

That visit with Tony was one of the last times I saw Nanny alive; she passed away on Halloween just a couple months shy of the world turning upside down. In the aftermath of my breakup, my therapist observed my cynical outlook on the prospect of ever finding love again. After lamenting I would never be so lucky to find another man who enjoyed my body as much as everything else about me, she assigned me homework designed to get me to treat my body with kindness: standard self-esteem activities like writing out things I like about myself and saying kind words to my fat belly.

“They aren’t working,” I told her, two weeks later. “Tell me more,” she said. She always says this. “Look, I don’t have self-esteem issues. If anything, I walk around too confident. I float through life thinking I’m a better-looking version of myself until a candid photo reveals to me a stranger.” 

“What else you got?” We sat in weighted silence.
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“So why don’t you think you’ll find another man who will think you’re sexy and desirable?” “Sexy!?! Pffffft. Who said anything about being sexy?”

A quizzical brow formed.“Well, you just got done telling me how confident you are,” she said. “Yeah, I’m not ugly but I am most certainly incapable of being sexy. Why should that even matter anyway?” I reply without any semblance of irony. 

“Here’s what you’re gonna do. I need you to buy lots of sexy underthings. Feel your own body. Get some nice-smelling lotion and just be with yourself this week. And I know it’s a pandemic, but if you see a cute guy, let’s try some flirting, okay?” 

I agreed to try, but I felt queasy at the thought of trying to flirt, or worse, buying some lacy contraption for an audience of no one. It occurred to me that the person who would ace this assignment would have been my grandmother. I mean, the only reason I know is because I lost count of how many times that woman walked around with an open silk robe, her exposed bra broadcasting an attitude impervious to criticism. 

But I did promise to try. 

That week I ordered a silk robe, not unlike the ones Nanny used to own, some lingerie, and after spending twenty years hiding my very large breasts in utilitarian, high-coverage brassieres, my very first deep-plunge, push-up bra. One night, as I caught myself grabbing my penguin pajamas, I glowered in my closet at the lacy negligée with the tags still on. I took a deep breath, slipped the fabric over my head, and sat down on my couch with a jar of lavender body cream. Just a girl, alone in the pandemic, watching Schitt's Creek on Netflix in lingerie. Sheepishly, I’d hoped that putting on the damn thing would magically turn me into some sort of sexy minx, but save for the moisturizing benefits of the lavender cream, all it did was make me feel very cold. 

I relapsed back into cotton and started flipping through a photo book my sister had recently gifted me to memorialize Nanny: a collection of pictures of her as a young woman, all crop tops, bikinis, and sultry cigarettes. How did she do it so effortlessly? And why did my apple fall so far from her tree? I remembered the other guidance to try flirting. For weeks, I’d been gushing about a guy I’d met in an online writing class, the first attraction I had since the breakup. I’d slowly worked my way into a series of zoom calls with just the two of us where I waited for him to be dazzled by my intellectual prowess, but after this assignment, it occurred to me that most humans rarely describe flirting as a cerebral exercise. 

Maybe I had been going about things all wrong. Then I remembered the push-up bra. I readied myself with a low-cut top and a bold red lip, and as we caught up on our latest writing assignments, I tried to smile more and do that hair-tossing thing.

I resisted all urges to adjust my top up to my usual neckline and reminded myself no one ever died from a little cleavage. 

As the call continued, I was so proud of my efforts; I believed this would be the breakthrough. Thirty minutes in, he let me know he had to hang up and get ready for his date that night. Just another fish in the sea of intellectual platonic playmates. 

I tossed the push-up bra aside, wiped the lipstick off, and sat down to have myself a good cry. 

Change seemed impossible. I lit up some sage and proceeded to fill my room with whatever positive energy I could muster before sitting down to meditate—hoping to make some sense of these feelings. As the sage smoke wafted, the aromas clung to the fibers of my clothes. Suddenly I was reminded viscerally of Nanny’s old apartment. I opened my eyes and was drawn towards the beautiful dancer hanging on my wall. 

Wild may it sound, but in that moment, Nanny’s presence was alive and well in my living room, the only person in the world who could help me. I thought of all the times people snickered behind her back or never took her seriously; I remembered how fiercely intelligent and elegant she was. I spent most of my life missing out on the fact that Nanny was showing me a woman can be many things at all once: vulgar and elegant, cerebral and sexy. I thanked her in that moment and promised her I would try not to forget. 

2020 is over, the world is still locked down and I can’t say I’m any better at flirting. Just the other day, I found myself giving a new man my phone number only to be met with the sort of contact exchange only seen at business networking functions.

But I am undeterred, and I realize now that sex and relationships are not necessarily the measures of success in the pursuit of sexual confidence. For as many relationships Nanny had in life, her authenticity was unflappable whether she was alone in her apartment, in a nursing home or in the company of handsome men. A year after her passing, she continues to teach me things I wish I had bothered to learn while she was alive. 

Not all angels wear white. Some wear leopard print and tell you dick jokes.