My gaze scanned the colorful racks of clothing and stopped abruptly on something I’d never expected to see: my boyfriend was clutching a wedding dress – that he wanted to buy for himself.

“Emily!” he cried with victorious glee. “I’ve found the one!”

Ian thrust the white garment into the air like a Nascar trophy. Its lace sleeves sashayed from the tapered bodice and fluffy tulle grazed the dirty tiles of the thrift store floor. A smile stretched across Ian’s scruffy face and his blue eyes danced with the giddy excitement of a bride saying, “I do!”

“Oh, wow,” I managed to spit out.

We were at Goodwill searching for dresses to wear during the annual Mother’s Day Climb up Mount St Helens, a decades-long tradition in which everyone scaling the volcano that day sports flowing garments in honor of female mountaineers and mothers everywhere.

I knew Ian would be among the most outrageous on the mountain. My boyfriend is aggressively fun and a flair fanatic, which I find wildly attractive on most occasions – like when he’s scaling technical slopes in jorts and a cat shirt or skiing the steepest lines in the Pacific north-west in space tights.

But I found myself unexpectedly uneasy with his new fondness for feminine frocks – a reaction that challenged the progressive ideals I’d prided myself on for decades. I’d long thought I was contributing to a progressive shift in how we define masculinity, finally allowing men to be emotional and vulnerable, or to ask for help, or to hug their male friends … or to wear dresses.

Ian giggled. “Isn’t it beautiful?” His chest hair battled the sheer neckline. The skirt fanned out as wide as a beach umbrella – a garment fit for a Vegas chapel.

I imagined him skiing down Mount St Helens in it, the lengthy rag concealing his chiseled calves and hardened quadriceps, and strained to find it an appealing vision. It was too much – even for him.

Emily Halnon with her boyfriend, Ian. Photograph: Emily Halnon

This was not the first time I’d found myself a little uncomfortable with the sight of Ian in women’s wear. It’s not an unusual sight to spot him sporting a skirt, dress, or sarong at a party, picnic, or trailhead. He uses his unconventional apparel as a display of his individuality and a reflection of his fondness for fun. I adore both of those qualities, but I was realizing I was less fond of seeing them exhibited through floral numbers or tight sequined garments or wedding dresses.

While it was attraction-at-first sight with Ian, his closet full of feminine gear put a tiny dent in his desirability from the very beginning of our relationship. Not enough to stop me from acting on my huge crush, but enough to notice there was an unexpected disconnect between what I thought I was OK with a man wearing, and what I actually found appealing on his body.

On the first weekend we hooked up, I had to yank a green sparkly dress over his head to unclothe him. Foreplay involved palming his glittery glutes while dancing to Kesha’s Woman and caressing his furry thigh along a hemline so tight you could almost see the outlines of each and every hair follicle beneath it.

“That was the first time I’ve undressed a man – from a dress!” I shrieked the next morning. My palms slapped the concrete countertop as I regaled my housemate Eli with stories from the night before.

“Oh girl, what an exciting milestone! Congratulations!” hollered Eli, an effervescent gay man who dons many dresses himself and is supportive of any man excited to do the same.

Intellectually, I enjoyed that Ian was rejecting gender norms and expectations. But physically, my desire didn’t match.

Those feelings illuminated some unanticipated boundaries of where I define attractiveness in men and when I still crave traditional masculinity. I realized I wanted less dress and more flannel shirts, trucker hats and sandstone Carhartts.

When we left the store that day, Ian had a big bundle of wedding dress and I had some big questions to consider.

•••

It was skiing that introduced us – we met on the snow-smothered summit of a mountain. He peeled back his Gore-Tex glove to plug my number into his phone, where it still lives under the contact “Emily Let’s Ski!”

One of our first dates was skiing on that same mountain. The 75-minute drive to its base was filled with surprisingly open dialogue about relationships, values and family matters. He told me about the companionship he sought through dating, the Tinder dates he endured in hope of finding meaningful connection, and the struggle of forging deep friendships such a great distance away from his family on the east coast.

When he asked me how it was to live 3,000 miles away from my family in Vermont, I choked up and revealed how challenging it’d been in the wake of multiple cancer diagnoses that had slammed my immediate family in recent months.

“I – I don’t know how to be wholeheartedly supportive from across the country,” I stammered. “I’m missing so much time with my family and it’s so hard to be caring and helpful from so far away.”

“I’m so sorry, Emily. I can’t imagine how hard that must be,” Ian’s voice softened and dropped to a compassionate whisper. He pressed his fingers deeper into my fleece jacket.

My last relationship had crumbled after my mom’s diagnosis. My ex-boyfriend had the emotional depth of a paper airplane and couldn’t engage with the deep pain I was enduring – or any other emotion, period.

When I started hanging out with Ian and he immediately wanted to talk about feelings, it was a gulp of ice-cold lemonade on a 98-degree day. I’d been craving this vulnerability and openness from the men I dated. Conversations like that one in the car drew me to him like a charged magnet, as did hisemotional openness, his fondness for communication, and his public displays of affection for close male friends.

My boyfriend’s wedding dress pushed me to perform a scrupulous inventory of my deepest ideas about masculinity and helped me identify my shortfalls as a woman who wants to help rewrite gender norms. As I went through this exercise, I chatted with a handful of girlfriends about it, who could all identify their own small hang-ups with masculinity: their need for men who are bigger and taller than they are, or who are better than them at sports, or who don’t cry in front of them.

As we interrogated our feelings about masculinity, we recognized gaps between our ideals and reality. I’m quick to blame men for perpetuating toxic behavior, but in this case, I, the woman, was part of the problem.

•••

Mother’s Day dawned sunny and crisp in the Washington Cascades. It was a beautiful day for a wedding dress.

On our procession up the mountain, Ian lingered back from our group of friends to check-in with me about my emotional state, aware of the added pain of coping with a sick mother on a holiday dedicated to moms. He wrapped his lace-doused arms around me and pulled me into folds of white fabric.

“I’m here if you need anything, babe,” he reminded me.

After we reached the summit, Ian plunged down the frozen slope, his long, white train flowing behind him, whipping from side-to-side like a lacy windsock.

“Do you find your boyfriend as attractive as I do?” whispered Eli, as we watched Ian plant his poles confidently in front of his flowing skirt, his hairy and silky chest beaming proud against the horizon, his laughing smile nearly detectable through the back of his floral sunhat.

My eyes chased my boyfriend down the mountain, my sensitive, silly, affectionate, emotional, vulnerable boyfriend – skiing in his wedding dress.

“I do,” I promised.