Cate Roser

I had little idea of what to expect as Yale’s infamous Halloweekend approached. I had heard whispers about it in passing, tales of wild parties and creative costumes, but it always seemed like something I’d never be part of. 

In mid-September, I was sitting on my common room couch with two friends when one of them suddenly asked, “What are your costumes for each night?” I was stunned. Not just because they had already begun planning their outfits, but because they were planning multiple costumes — apparently, three to five was the norm. I had barely thought about one.

That night, as I lay in bed, I felt a new wave of stress piling on top of an already-looming orgo midterm: I needed to figure out my costumes. The thought of dressing up for four consecutive nights was daunting, but even more unsettling was the idea of being an outsider. I stared around my room, my eyes landing on a pile of untouched laundry, then drifted to my laptop, still open to notes on stereoisomers. But my thoughts weren’t just on school work; this wasn’t just my first Halloweekened, it was my first ever Halloween. Growing up in an Orthodox Jewish household, Halloween was viewed as a sacrilegious manifestation of secular indulgence. Now, though, the weekend felt like more than a holiday. It could be a defining moment of my first-year fall — an opportunity to shed the skin of my upbringing, even if just for a few nights.

As I wrestled with my costume dilemma, I thought back to what Halloween had meant before college. Growing up, I’d spend Oct. 31 perched at my windowsill, watching parades of giddy trick-or-treaters as they dashed from house to house. Sometimes, one of them would mistakenly approach our door, only to be met with a swift dismissal from my parents: “We don’t celebrate Halloween here.” The response was a refrain I’d heard all my life, echoing the broader consensus of our community, which chose isolation over participation. The trick-or-treaters would scamper off, none the wiser to the cultural dissonance that had informed their rejection.

My participation in Halloween was limited to silent costume critiques from the window, rating witches, superheroes and princesses in my head. Even as an 8-year-old, I’d wonder what it would feel to be among them, holding a bag of candy and feeling the excitement of the night, rather than just observing it. I longed for the freedom of expression that came with dressing up, but that longing was always tempered by an awareness of the restrictions that defined my upbringing. 

I tried to ignore it, but Halloween became a symbol of everything I couldn’t have: a microcosm of the broader tension between my desire for normalcy and my enforced duty to tradition.

My upbringing wasn’t just marked by a lack of Halloween — it was defined by a broader sense of religious dissonance. Attending a strict Orthodox high school, I often felt disconnected from the gender roles and societal norms that were ingrained in each of my Judaic classes. While I was required to find comfort in tradition, I instead felt constrained by it, craving a more progressive and nuanced approach to spirituality — one that could accommodate questions and contradictions rather than shut them down. 

For years, I adhered to the rhythm of Orthodox life: I kept Shabbat every week — avoiding all forms of work, technology and travel from Friday sunset to Saturday night. I celebrated all Jewish holidays, ranging from Rosh Hashanah to obscure fast days, and from Passover to Sukkot. But as I entered college, I felt compelled to explore the secular world, leaving behind some of the restrictions that had once shaped my identity.

Even so, I haven’t entirely let go. I still find myself at the Slifka Center every Friday night for Shabbat dinner — yet not out of religious obligation, but for a sense of community. The familiar rituals offer a comfort that transcends belief, making me feel culturally connected even as my spiritual adherence wanes. It’s a complicated relationship — one that’s more about finding harmony than complete abandonment.

Now armed with four costumes — ranging from Paddington Bear to SpongeBob — I embody the absurdity of my transformation from a windowsill observer to a full-fledged participant in one of Yale’s most hyped traditions. My half-serious attempt at embracing the school’s competitive costume culture brought a mix of excitement and trepidation. It was thrilling to finally step into a world I’d only ever watched from afar, yet it also felt like I was betraying the values I’d been raised with.

Last night, before “Hallopaluther,” I stood in the mirror with a half-knotted tie around my neck and a backward hat laid carefully on the head — my first dress-up attempt manifested as being “Magic Mike” with a group of friends. Looking at my reflection, I felt ridiculous but also oddly liberated. As I stepped out of my dorm, ready to join the chaos of Halloweekend, I realized that this was more than just a college rite of passage and the start to a week of fun. It was a personal one, too — a chance to redefine my relationship with a holiday I’d always kept at arm’s length, to reclaim a bit of the childhood I’d never really experienced. 

As the night unfolded into a whirlwind of dancing, laughter and new friends, I felt a surge of newfound belonging. It wasn’t just about Halloween anymore — it was about allowing myself to finally be a part of something I’d always watched from the outside.