Week One: A Mystery Man

How could a city like Boston feel so small when estimated 700k people allegedly call it home? Yet somehow, every time I stroll down Columbus Ave for a martini stop at Anchovies, it turns into a gay reunion. You either know them, or you know someone who’s kissed them. In Boston’s gay world, there are only two categories: the familiar and the mysteriously new. And when I meet one of those rare, unconnected gays, someone without mutuals, without history. I literally feel like Scarlett Johansson in Marriage Story, dancing alone and wildly free. Maybe that’s the problem. Maybe I’m addicted to the high of discovery, and that’s why love keeps eluding me.

How to Find the Mysteriously New Man

So, how do you find the mysterious new man in a city where even your friends interest always seems to dock right after yours departs? Step one: get off those damn apps. Boston isn’t small, it’s just socially claustrophobic. There are gays tucked into every corner: the DL Southie men, the college bros of Cambridge, the JP plant dads, and, not to forget, the Back Bay married couples looking for their additional roommate. They’re all out there, for everyone, living their perfectly curated little lives. But maybe the real secret isn’t swiping right.... ITS SIMPLY SHOWING UP.

One way I’ve managed to keep meeting new, mysterious men is by exploring new hobbies. My favorite part about Boston is the endless lineup of LGBTQ+ sports and social communities. GURL, Stonewall Sports Boston, PRIDE Sports Boston, Tennis4All, and even most gyms. The mysterious new man might be standing right next to you, equally tired of digital love, and finally ready for something that feels real.

Upcoming Events and Unwritten Stories

They say love can’t be scheduled, but who’s to say it can’t be penciled into your calendar? As Halloween creeps closer, the gay social season hits its chaotic peak. It’s the one time of year when being a total menace is encouraged. For one weekend only, everyone’s libidinous gets a hall pass, and honestly? It's so fun.

Oct. 25 – GURL Hike, Mount Chocorua (NH)

Nothing says “new beginnings” like gay men voluntarily hiking before noon. The GURL crew is taking on Mount Chocorua, with a rain date of October 26th, because Mother Nature clearly knows how to play hard to get. Between the switchbacks and shared trail mix, who knows? You might find your mystery man halfway up the mountain… or at least someone to cram in a car back to Boston with.

Oct. 25 – Tennis4All Halloween Social (Woburn, MA)

If cardio and costumes are your idea of foreplay, this is your court. It’s part Halloween, part doubles play, and entirely an excuse to flirt through a rally. Bonus points for anyone who can serve and seduce at the same time.

Oct. 26 – Stonewall Sports Kickball Tournament

Think of it as the gay Olympics, but with shorter shorts and higher drama. Whether you’re in it for the competition or the post-game beers, this is where team spirit meets potential team dating.

Oct. 30–Nov. 2 – Spooky Bear Weekend (Provincetown, MA)

Every year, Provincetown transforms into a haunted playground of harnesses, flannel, and diva icons. It's PTOWNs last vibrant weekend of the year, with tea dances, bar crawls, and late spooky nights. Whether you’re chasing trade, goons, or just a good time, it’s the kind of weekend where a “boo” might actually text you back.

Nov. 7–10 – PRIDE Sports Kickball Tournament (Austin, TX)

Boston boys are traveling south for one of the biggest queer sports weekends of the year. It’s a chance to trade your hoodie for a tank top and your situationship for a Texas fling. After all, everything is bigger in Texas? Stay tuned...

Because maybe the mysterious new man isn’t hiding on an app at 2 a.m. maybe he’s standing across a kickball field, or hiking up a mountain, or serving aces in a Halloween costume. Sometimes, the best way to meet someone new is simply to show up and let the story unfold from there.

Tricks, Treats, and Trade

Hot or Hilarious Costumes?

When it comes to Halloween, I’ve had luck with both. Sure, the hot costumes get attention, but sometimes, mystery thrives under a layer of polyester and face paint. If you’ve got the personality to match an unconventionally attractive costume that covers most of your skin, you still have a real shot at luring in the mystery man. In fact, maybe an even better one. There’s something magnetic about someone confident enough to go obscure or ironic because if he recognizes your niche reference, congratulations: you’ve just met a man with both taste and imagination.

Finding Manhattan Magic

This year, I’m missing Spookybear for the first time since living in Boston and honestly, I’m a little heartbroken. Provincetown in late October is one of the largest Boston gay odyssey. But instead I’ll be in NYC, visiting my besties and pretending I don’t have FOMO. Part of me knows it’s the right choice, because if there’s anywhere else on earth that I can find Mr. Mystery Man, it’s in Manhattan. And who knows? Maybe I’ll make an appearance at Heidi Klum’s Halloween party and get lost in NYC nightlife. Either way, I’ll still be chasing that same thing, connection, chaos, and maybe a little magic under the club lasers.

Conclusion

This year, I’m doing something different. I’m stepping away from my usual haunts. The comfort of Boston’s familiar faces, the chaos of Spooky Bear weekend. It’s strange, isn’t it? How we cling to what feels like home, even when we say we want something new. Maybe finding my mystery man isn’t about orbiting the same bars, gyms, and drag shows, it’s about changing my orbit entirely.

Halloween has always been about transformation. For one night, we get to become someone else. But maybe the real costume I’ve been wearing is comfort. And this year, I’m ready to take it off. Because love, like Halloween, isn’t about who you pretend to be, it’s about daring to reveal what’s underneath. And as I trade Boston’s ghosts for new adventures, I can’t help but wonder… maybe the scariest thing of it all isn’t being alone. Maybe it’s realizing that growth means getting a little uncomfortable. See you soon NYC. XX