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The Snowflake Diaries: Screw ‘Boyfriend Jeans,’ I Wore My Girlfriend’s Jeans for a Day

To be a boyfriend to a woman, be prepared to share your clothes. This garment-borrowing manifests any number of ways: In our apartment, it usually means the discovery that my girlfriend, Madeline, is already wearing my favorite oversized sweatshirt when I get back from a run on a chilly evening with the idea of throwing that exact hoodie on after a hot shower. In theory, I could be annoyed — but she looks so damn snuggly and cute in anything that comes down to her knees. There’s something hormonally satisfying about the exchange of scents, too.

Madeline’s own wardrobe boasts bold patterns and blouses collected in the course of devoted thrift-store shopping; I’d be lying if I said I never considered trying them on. Sadly, our size difference is so substantial, and her best vintage pieces are so fragile, that I’d split most of them in half just putting my arm in. Inspired, however, by the brand-confirmed existence of “boyfriend jeans” — and always an advocate for gender equality — I struck upon the idea of wearing a pair of her pants for an afternoon. They say to walk a mile in another person’s shoes to know them, but there was no hope of forcing her tiny clogs onto my flipper-like feet. Jeans were my only hope.

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I picked the ideal occasion to force myself into clothes that probably wouldn’t fit regardless: The day following Thanksgiving. (On top of that feast, where I’d enjoyed a fourth helping of stuffing for dessert, we’d just eaten a huge brunch at the local diner.) Madeline was amused by the suggestion, though mostly skeptical that I’d manage to wriggle into her size 4s, which only made me more determined. Why should this sartorial cross-pollination go just one way? Nevertheless, there was a decent chance I’d rip the jeans, causing a rift of resentment for the rest of the weekend. I was taking a big risk by asserting my right to her pants, and I hoped it was worth it.

At home, she gave me two options: One pair turned out to be an example of the aforementioned “boyfriend jeans” style, and while they weren’t even close to my normal measurements (34”x34”), I still regarded this choice as cheating. I resolved, therefore, to concentrate my efforts on the American Eagle offering, which included the promise of “stretch” to accommodate my frame. Knowing I’d be facing a tight fit, I discarded my boxers in favor of a pair of briefs I keep in case of such an emergency. I then worked up a sweat snaking my legs into the skinny denim, soon realizing that the hardest part of this would be jamming my feet through what felt like pinhole-wide holes at the bottom. That accomplished, I zipped and buttoned the fly with ease.

“Wow, pretty tight,” Madeline said, confirming the sense of constriction I now felt from my thighs to my groin to my calves. “They make your butt look good,” she added. Odd, since it seemed like I couldn’t actually keep the belt line of the jeans above the band of my underwear, creating a trashy low-rise look I didn’t totally love. Meanwhile, I got a kick out of how well-defined my legs became — the jeans were so snug that they read like leggings. At a glance, you might think I was headed to ballet rehearsal, or yoga class. Most surprising of all, the length was totally adequate. At 6’2”, I was expecting a pronounced capri effect, yet the cuffs met my ankles. Go figure.

Of course, it’s one thing to pose in your significant other’s pants at home, quite another to face the world in them. Both of us needed to do some work, so we packed up our laptops to head to the coffee shop. We wouldn’t be walking, either, but availing ourselves of the personal transportation most popular in these parts: bikes. This was undoubtedly the greatest challenge of my day. Before we’d left, I’d noticed how hard it was to bend over in Madeline’s jeans; bending my knees to pedal my bike was even more difficult. To make matters worse, my briefs were wedging themselves further into my buttcrack. Somehow, out of all this frictional discomfort, my body took a measure of arousal, and I noted the confused beginnings of an erection. With no room in the crotch to grow, this unfortunate boner strangled itself at half-mast.

Downtown, hyperaware of my lower half (and the bizarre inadequacy of the pockets affixed to women’s clothing), I braced myself for reactions. The coffee place has the forwardly friendly vibe of many such establishments in California — a positive comment from the barista about your hat or shirt is not out of the question, and the other week, an employee at the register earnestly said: “I like your freckles.” If anyone would be bold enough to comment on my girlfriend jeans, it was going to be this staff. But neither they nor my fellow customers did so much as a double take. Turns out there’s nothing all that transgressive or remarkable about cutting off your circulation with pants whose elasticity is challenged every time you flex your hamstrings.

Indeed, within an hour of sitting down to write, blood flow was all I could think about: I got pins and needles; my ass fell asleep, and my testicles throbbed. Below my hips, and where the rim of the jeans cut into my belly, everything ached as if I’d spent the night sleeping on a pull-out couch. Like any relatable human being, I love getting home and taking my pants off, but now I began to understand why for Madeline — and doubtless many other women — it comes as an even greater, ecstatic relief: Their jeans are an unforgiving challenge of endurance. Minute by minute, it was as if my legs were suffering a slow death by suffocation and irreversible atrophy. I feared I’d burst the stitching like the Hulk, revealing pale hairiness instead of green skin.

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Across the table, and wearing my jeans, Madeline appeared more at ease. Though a bit lumpy in the front, requiring some roll-up adjustments and a close-cinched belt, they demonstrated no drawback besides a basic dad-ish dorkiness. I suppose at this point I accept that the woman in a straight relationship has all the advantages in combining closets, and that I’ll have to make do with a significant subset of unrelated male privileges. Yet I can’t abandon my vision of a utopia where Gap sells “girlfriend jeans” for men as well as for women — where mankinis are plentiful and the fashion industry recognizes this desire to play with my feminine side now and then.

Maybe, by the time I get these pants off again, we’ll have made some progress on that.