Halloween has always been a time for costumes, candy, and creativity, but for me, it became something far more profound during my first year in college. Let’s rewind to 1998, to a version of Halloween I’ll never forget—one that gave me a taste of freedom, independence, and a deeper sense of self-expression that I never knew I was craving.

Breaking Free from a Catholic Upbringing

Growing up in a strict Catholic household, any exploration of sexuality or femininity felt like it was immediately labeled as “sinful.” My family’s values instilled a strong sense of modesty and a rulebook for “appropriate” behavior that left little room for self-discovery. At home, Halloween was mostly for children, just another holiday on the calendar to dress as something innocent or funny. But I’d always sensed there was more to it, especially when I’d see glimpses of teenagers dressing up as bold characters—people they weren’t in real life but could embody for one night. This curiosity simmered, and when I got to college, far from family watchful eyes, that curiosity exploded.

Dressed as the Latina Version of Pretty Woman

I’ve always loved Pretty Woman and that Halloween, I decided to dress up as the Latina version of her. In that choice, I wasn’t just picking a costume—I was choosing a version of myself that I hadn’t been allowed to explore. I saw this as my shot and I took it. For the first time in my as of then short lived life, I could embrace a confident, alluring character who wasn’t afraid to be seen. Running that red lipstick across my lips, ripping my pantyhose, and glamming up gave me permission to express a part of me that had always been repressed. Right away, I felt it. There was an excitement in the air, an energy that felt so different from the roles I’d been told to play growing up. For the first time, I felt in control of how I presented myself and how I wanted the world to see me.

That 1998 Halloween, I was testing out a version of myself that was new, unexplored, yet powerful. And in doing so, I discovered a new layer of joy—a freedom in self-expression that I’d never felt before.

That entire night I was so annoying and I knew I had hit on something.

Halloween as a Gateway to Sexual Exploration and Freedom

Halloween, for many, is just a fun holiday with no deeper meaning, but for me, it became an outlet for sexual exploration and independence. Halloween provided a safe way to step out of the box. There was a thrill in embracing a new version of myself, knowing that it was only for one night but also realizing that it was something I could keep with me moving forward if I chose to.

For those of us from more conservative or religious backgrounds, this holiday can offer a glimpse into different possibilities—ways of expressing ourselves that feel authentic, even if they’re not encouraged by our families or communities. In a way, Halloween taught me that I had the power to define my identity, and I didn’t have to conform to the expectations I grew up with.

How that First Halloween in College Changed Me

It’s funny to think that a holiday known for dressing up as someone else could lead me to feel more like myself. Looking back, that night was about much more than the costume. I was celebrating a newfound autonomy, the ability to make choices just for me without fear of judgment. Halloween became my celebration of freedom—a safe space to let go of the expectations and enjoy being young, bold, and, yes, a little rebellious. In a way, I was “partying like it was 1999” before it actually was 1999!

As Halloween approaches each year, I’m reminded of that experience and how it paved the way for me to keep exploring who I am, and become the person I am today. It today me that is okay to continue to explore the many layers of my identity and not to judge myself and others for doing so. That first college Halloween was transformative, a coming-of-age moment that continues to resonate. It taught me that sometimes the boldest choices can lead to the most freeing experiences.

Reflecting on Halloween Today

Today, Halloween is still an opportunity for people of all ages to explore different sides of themselves. Whether dressing as a beloved character or creating a new persona, it’s a night that gives everyone permission to play, explore, and even flirt with boundaries that might be off-limits the rest of the year.

So, to everyone out there celebrating this Halloween season, remember: sometimes, it’s about more than just the costume. It’s about discovering who you are, one costume at a time.