Bachelor in Paradise
On love, bachelor parties, impermanence, and the bittersweet taste of major life milestones
“How lucky I am to have something that makes saying goodbye so hard.”
— A.A. Milne, Winnie the Pooh
Nothing forces you to confront the ecstasy and absurdity of weddings like planning one. As mine rapidly approaches, I find myself caught between immense waves of love and loathing.
In the spirit of 2025, let’s start with the loathing.
Here’s an abridged list of things I currently l loathe about weddings.
People who wing speeches that shouldn’t (which is most people). At best, bad speeches bore people into drinking more. At worst, they ruin the night and divide the very people meant to unite.
The cost. Even the 'optional' expenses feel mandatory, framed in a way that makes you second-guess your choices. Here’s the kind of stuff you’ll hear from well-intentioned vendors, venues, and even your saint of a wedding planner:
No, you don’t need signage, but guests have been known to wander off and fall to their deaths on the nearby cliffs
You can opt out of a cake, but the hotel will still charge you for serving or not serving a dessert—your call.
You don’t need a rain plan, but if you do want one, you need to rent this tent for eight grand, which you’ll likely not need to pay , but to justify the rental contract existing you will need to rent three thousand dollar’s worth of napkins, tables, and chargers.
Chargers: oversized plates with no purpose. Like their cousins in the NFL, they please no one and should go away
My biggest wedding grievance doesn’t fit within a snide bullet point.
It isn’t logistical, it’s existential, and it’s the real reason I’m writing this.
It’s long felt unfair to me that your wedding is the only time when all of your people—family, childhood friends, college friends, work friends—align in one place, in a way that will never fully happen again.
For a while, I chalked this up to my inner herding dog.
For a golden retriever with a Substack, joy is gathering my favorite people in one place; heartbreak is watching them scatter.
This explains how I’ve structured every birthday party since COVID ended: spending a fair amount of time and money setting aside a time and place to invite everyone who can attend and spend a few hours or ideally a few days playing games, eating, drinking, and laughing together.
However, loving a full house doesn’t explain why I grieve when it empties, which brings me back to weddings.
For all my cheeky complaints, I’m not worried about my wedding. What I’m worried about is the day after, the inevitable comedown.
When I tell people this, I often get some version of Dr. Seuss’s platitude: “Don’t cry because it’s over; smile because it happened.”
This helps, but it doesn’t explain why big, joyful moments leave me feeling as sad as they do happy.
This, I only fully understood after coming home from my bachelor party.
If weddings are about tight schedules, high expectations, and carefully choreographed moments, bachelor parties are the opposite. They’re sprawling, unstructured, and unserious—the rare chance to exist in a pocket of time where nothing matters except the people you’re with.
My friend Jack’s joint bachelor-bachelorette party at his grandparents' house in rural Pennsylvania was where I first learned this in 2019.
It felt like summer camp for adults—three days of floating on the lake, drinking by the dock, and basking in the kind of nostalgia that only childhood friends and childhood homes can conjure. I spent one golden, glorious afternoon on the floating dock, sipping wine and getting to know one of Jack’s oldest friends. The only downside of the weekend was seeing my first Confederate flag on the drive in.
The joint format, besides the obvious pluses for gender equity, also struck the perfect balance between big group hangouts and smaller break-off moments. On night one, the guys (plus Jack’s childhood friend Cat) watched The Mummy (1999), while the women (plus Hannah’s friend Dave) watched Mamma Mia! (2008) The plan derailed on night two when we tried to watch The Mummy Returns, only to realize someone had stolen that disc from the boxed set Jack had borrowed from the New York Public Library, leaving us with the putrid The Mummy: Tomb of the Dragon Emperor.
Even this misfortune couldn’t ruin our moods, because most of what we wanted to do was drink, talk, and float in the lake anyway. The vibe oscillated between sweet, appreciative, and deeply unserious—a rotating chorus of lifelong friends giving Jack beer and compliments, blasting Carly Rae Jepsen, and re-litigating an infamous sandwich theft from our freshman year at Kenyon.
By the end of the weekend, I was ecstatic, thoroughly charged with nostalgia, and convinced: when it came time for my own, I’d do a joint bachelor-bachelorette party, too.
Though I had to wait four years for my next one and longer still for mine, my friends bachelor parties had been a delightful kaleidoscope of experiences across the country: Oakland in April 2023, New Orleans in March 2024, and New York in May 2024.
While the locations have varied, the vibe has not.
Every bachelor party crackles with anthemic camaraderie—The Boys Are Back in Town, but with more Lord of the Rings references. What I love most about them isn’t the binge-drinking or indulgence, but the sheer expanse of time together—the inside jokes that evolve into their own dialect, the soulful nourishment of over 48 uninterrupted hours of friendship. For me, the motto of a good bachelor party isn’t “What happens in Vegas stays in Vegas.” It’s “If you can’t stop laughing about it later, you did it right.” The best part of them isn’t some clichéd or clandestine debauchery—it’s the effortless absurdity, the moments you can describe but never quite explain to someone who wasn’t there.
At Jack’s, I stepped out of my room wearing a matching jungle-print shorts, shirt, and bucket hat combo I’d impulsively bought at Target before a frisbee tournament. Without missing a beat, every guy in the house locked eyes, grinned, and began chanting “Imhotep”—the name of the villainous high priest in The Mummy—as if compelled by some ancient, collective memory.
At Ffej’s, we were sailing around Alcatraz when I took it upon myself to be the Pacifico lime guy. I had a plastic lime-shaped squeeze bottle in my jacket pocket, and every time someone reached for a beer, I’d swoop in to add a precise, zesty squeeze before handing it off. I did this so seamlessly and ritualistically, that by the end of the ride, one of Ffej’s friends who I’d compared lists of fake indie band names with earlier in the day turned to me, dead serious, and asked, “Do you always carry lime juice on you?”
At Matt’s, we waded through the chaotic blur of a New Orleans St. Patrick’s Day parade, dodging flying cabbages and beads as they rained down from revelers on floats. Hours later, back at the Airbnb, still draped in green plastic necklaces, we launched into yet another game of Baseball (the drinking game, not the sport). When the 7th-inning stretch rolled around, we all stood, swayed, and belted out “Take Me Out to the Ball Game” like a group of over-served, off-key baritone choir boys.
At Kevin’s, after inhaling spicy lamb noodles at Xi’an Famous Foods, we took the subway to the Bronx to see Aaron Judge in all his hulking, athletic glory—a man so physically imposing that I found myself taking zoomed in photos of him to send to Alexis. After many tallboys, we left the stadium, slowly migrated South, and made what we thought was a reasonable decision: ordering Halal food at 3:30 a.m. It was so good that ten minutes later, we got back in line and ordered it again.
For a while, I entertained a theory that only someone who hadn’t gotten married yet would have: on a pure fun-to-participant ratio, a bachelor party might actually be better than a wedding.
Weddings are beautiful, but they’re also a blur—packed with speeches, logistics, and a hundred tiny pressures to make the most of every moment. Bachelor parties don’t have that weight. They unfold at their own pace, expanding to fill the space you give them.
If a wedding is the grand crescendo, a bachelor party is the deep breath before it—the rare, unhurried stretch of time where friendships build and settle, unbothered by schedules or expectations.
I really thought I had all of this figured out.
And then I had my own.
Our vision was simple if not frugal: a weekend in San José del Cabo with 18 of our closest friends and family.
However, after hours of fruitless Airbnb and VRBO scouting, we nearly scrapped the joint bachelor-bachelorette party idea altogether. Then we found it—a villa straight out of a Sofi Tukker music video.
With the location and guest list set, we got to work. We planned dinners, booked activities, and strategized about the right balance of time as a big group and smaller groups, carving out space in the schedule for both social time and downtime. Since the first night of the trip fell on Valentine’s Day, we wrote heartfelt notes to our friends and planned to leave them on their beds with a box of candy hearts—a small welcome, a reminder of how much they meant to us.
Everything was dialed in. All I had to do now was pace myself with the Pacificos and enjoy the weekend whose every contour I had so carefully imagined ahead of time. But just as things were reaching cruising altitude on Friday night, something strange happened.
I stepped out of the shower to find the house eerily quiet.
Everyone was gone.
Only Alexis stood outside by the picnic table beneath a tree, the surface covered in a spa-worthy spread of rose petals and candles.
Then, I heard it—the faint sound of music coming from a speaker hidden in the bushes, Sophie Park’s “Your Kind of Beautiful”
You see a lion and a sailboat in the sky
All I see is little clouds passing me by
You pick a dandelion and you make a wish
All I see is stubborn weeds growing in the ditch
And if I could be I would be be the way you be
And if I could see I would see see the way you see
Your kind of beautiful is beautiful to me
I turned to Alexis, confused.
“What’s going on? Where did everyone go?”
She didn’t answer.
She just sat me down, pulled out a small beige box, and opened it.
Inside: a gold ring.
And suddenly, it all slid into focus.
Alexis was proposing to me.
Until that day, every surprise Alexis planned for me had, without fail, been spoiled.
Sometimes, it was bad luck. Sometimes, forces beyond her control.
When she got me into the exclusive Rancho Gordo Bean Club, the first shipment arrived in a box proudly stamped with RANCHO GORDO—so much for the element of surprise. When she ordered me the Lego Rivendell set, a Lego magazine arrived weeks ahead of time—a dead giveaway, for my childhood taught me nothing if not that an unsolicited Lego catalog means someone in the house has recently purchased Legos.
Just as often I ruined the surprises myself. I have a habit of guessing gifts outright by casually suggesting we do the very thing she had already bought tickets for: Taylor Swift’s Reputation Tour. The SF Symphony playing the score to Jurassic Park.
This time, though, she got me. Completely.
Alexis’s proposal wasn’t just her first true surprise—it was also her best.
Only by being proposed to did I fully understand the joy of proposing. In that serendipitous blur of rose petals and candlelight, I saw our engagement nearly two years prior from the other side. This was the ultimate empathetic gift.
As the reality sunk in, I was floored by how much time, effort, and coordination must have gone into this.
We both cried, and I gave her the same expected, enthusiastic, and teary string of “yeses” she had given me in the UC Berkeley Botanical Garden nearly two years prior.
The aftermath felt just as surreal, just as glowing, as the first time around. We walked around the corner to the casita where many of our friends were staying—only to find them lined up on the roof deck, grinning ear to ear. It felt like my own version of the Marina Bay Sands party scene at the end of Crazy Rich Asians. They were all here. For us.
Hand in hand, we strode toward the house. I tilted my head up to the balcony and shouted:
“I said yes!”
A roar of cheers cascaded down.
“But I drove a hard bargain.”
Matt Bedrick shouted, “Congrats!” while Ffej, our officiant, asked, “When’s the wedding, again?”
Hugs and clinked glasses followed as the sun dipped into a postcard-perfect shade of orange.
And then, I noticed something else.
Everyone was wearing blue hats with red text that read: Fresh & Flirty—the theme and dress code of our wedding we had written on Zola. And on the back, in white, was he outline of a shark. When planning a wedding, some things are non-negotiable.
As the night wore on, over rounds of Pacificos, the full scope of the planning became clear.
The sheer number of people involved was staggering.
It had started months earlier. A dinner I thought Alexis was having with Hannah was actually a strategy session at Missouri Lounge with Matt Rowett. Over Mezcal Palomas, they sketched out Alexis’s plan to pull off a surprise I wouldn’t see coming—by planning it at my own bachelor party. What I assumed was an airport run to pick up Alexis’s sister, Ashley, was actually cover for Matt and Petra to sneak off to Walmart for roses. Kevin and Kaitlyn brought an absurd number of spa candles, then painstakingly disassembled the bouquets Matt and Petra had bought, petal by petal, to create the romantic tablescape. Charu spearheaded a hat committee, wrangling a group decision on colors—though the shark on the back was unanimously agreed upon as a mandatory design element.
Meanwhile, the rest of the crew decorated the house, stocked the bar, prepped a playlist, and sequestered themselves in the casita until the moment was right.
The result?
In the words of one attendee: “a total love fest.”
After the Casler sisters popped champagne and Matt Bedrick poured Palomas, we enjoyed a catered feast under the stars. Then Alexis and I hosted a Jeopardy! game themed around our relationship, with categories like “White People Nonsense,” “Turn Down For What,” and “True Facts Only Reilly Would Know” (there was some overlap between them). Despite a heroic late-game comeback, the men got absolutely steamrolled by the women.
On Saturday morning we ate chilaquiles at the house before splitting up. The women headed to the Instagrammable bucolic splendor of Flora Farms for a cooking class while the men went to play pickleball in what could only be described as a post-apocalyptic brutalist sports complex.
Saturday afternoon was pure bliss—lounging by the pool, sun-drenched and happily exhausted. At dinner with the guys at Lumbre, I turned to Matt Rowett and admitted:
“Today was perfect.”
It was true. Breakfast with my closest friends. Two and a half hours of fiercely competitive but wildly fun pickleball. A long, lazy poolside afternoon with Pacificos in hand. And then, Mexican food so good it could have ended my life on the spot and I wouldn’t have complained.
Yet somehow, Sunday was even better. All twenty of us piled into a bus, slathered in sunscreen and buzzing with anticipation, our matching hats making us look like an overgrown field trip.
As we rolled past a multi-story Señor Frog’s, Christina queued up “I’m on a Boat” by The Lonely Island.
Once onboard the catamaran, clutching mimosas and binoculars, we watched humpback whales launch themselves out of the sea like they were auditioning for a Pacific Life commercial. Like the whales, we had traveled to Baja to celebrate love—though, in fairness, our cushy flight put their 6,000-mile migration into perspective.
We thought the humpbacks would be the peak moment of the day—until a gray whale surfaced right next to the boat, like a submarine with no concept of personal space.
That afternoon, we napped. We swam. We soaked in the last golden hours of the trip. Then, as the sun dipped, the guys gathered outside for one last mezcal-fueled toast. One by one, they spoke. I cried. Again.
At dinner, the toasts continued. Not just at our table, but at a nearby wedding, where we were forced to endure some of the worst speeches ever conceived. The bride’s little sister took the mic to recount, in painstaking detail, the first three times they got drunk together. Her father followed with a deeply unnecessary monologue about how much he enjoyed beating the groom at pickleball, despite being twice his age.
I went to sleep that night deeply grateful. Not just for the trip—but for the certainty that no one at our wedding would dare to give a speech like that.
I’m so predictably, hopelessly sentimental that by Sunday night’s dinner Christina had turned it into a drinking game: Anytime I said “You guyyyyys,” everyone had to take a sip.
So it won’t shock you that the same guy who tears up at the key change in "Love Story" was also the kind of kid who melted down when his birthday party ended.
As I wrote in my Taylor Swift-themed account of getting engaged,
“I have long struggled with come downs after big life events, emotional hangovers that more than occasionally mingle with real hangovers and wreak havoc on my mood for days afterwards. This is perhaps the ultimate first world problem. Real life is just much less shiny, ebullient, and connected, I moped to Alexis on the morning after the Eras Tour.”
Nowhere was this more true than the Monday of our bach party.
By the time I woke up, the weekend was already slipping away.
The decorations were gone.
Breakfast tacos piled up on the counter.
Ubers arrived.
I hugged Lauren goodbye, and suddenly, I was crying again. Was it because her and I never played Spikeball? Because I’d had more drinks than hours of sleep for four days in a row? Or because I was finally accepting that this fleeting, transcendent weekend was actually over?
With joy comes the comedown—not just physically, but existentially. The shock of re-entering real life, quieter and lonelier than a golden afternoon watching whales breach the Pacific.
Back in foggy Berkeley, I collapsed on the couch and sobbed.
This was not out of sadness or exhaustion, exactly—more like an overload of love, love for the people who had traveled just to celebrate us, love for my friends, my brother, Alexis’s sister—for everyone who had done a hundred tiny things to make this weekend what it was: sending emails, cooking breakfast, buying water, washing dishes, and keeping the energy high for four perfect days.
Days like this make me loathe how sentimental I am. Other people have a great weekend and move on. I have to turn it into an existential crisis and blog post.
I hesitate to even write this because it sounds like the most first-world problem imaginable:
"Oh nooo, you had so much fun that going back to normal life is hard?"
When I complained to Alexis that this was probably the second-to-last time this exact group would ever be together, she gently reminded me that three-quarters of them live in the Bay Area and half of them were at our Super Bowl party the week before, so maybe my friends aren’t as far away as they feel on mopey Mondays and terrible Tuesdays.
Weekends like this are urgent reminders of what I actually want from my life and my friendships—not just sending memes back and forth, but running around outside, watching the ocean, giggling about the ubiquity of Cialis in Mexican pharmacies.
They’re also a reminder to make more of them happen. If you create a space worth gathering in, and occasion worth gathering for, people will come. This, after all, is literally the premise of a wedding.
But with this realization comes learning to live with contrast.
As I wrote after getting engaged:
“As Alexis and I have navigated life’s highs and lows together since 2017, she’s helped me understand that as wonderful as pop concerts, beachfront birthday parties, and boozy weddings are, these are the exceptions to the messy and mundane ways that we spend the majority of our time alive.”
It’s easy to revel in the build-up to these events—to imagine the perfect weekend, the golden memories, the inside jokes that will live forever. But when you finally step into the moment, it rushes past you faster than you can hold onto it.
Anticipation is a thrill; reality is disorienting.
There is also a comfortable cycle to all this—a rhythm of planting and harvesting.
What we felt in Mexico was the joy of picking a field we’d been watering for a lifetime. If joy is a harvest, friendship is a perennial—returning if you tend to it.
It doesn’t take much to keep it alive—a call, a dinner plan, a half-serious, half-joking group chat that never really dies. A little more effort—a flight booked, a weekend planned—and suddenly, you’re back in it. The field may look different, but the roots are still there. Good friendships don’t fade.
They just wait for the next chance to bloom.
As an adult, you only get so many rites of passage—and even fewer that warrant a full-fledged party: Weddings and maybe having a kid.
And even then, you only throw a blowout party for the wedding.
So when one of these mythic events finally happens, it’s dizzying—to build up to something for months, even years, to finally experience it in real time and watch it dissolve before your eyes.
These moments remind you: Love is rare. Togetherness is fleeting. Life keeps moving forward.
Even in happiness, there’s grief—the quiet ache of knowing nothing stays.
Maybe that’s why we create spaces, where for a little while, it does. For a few days, you live in a world untouched by emails, deadlines, or bills. Just games, laughter, and deep talks. It’s in these moments that I always feel the luckiest, looking around and thinking:
"Damn, I assembled a hell of an Avengers team."
When I look back at photos of that weekend, what stops me in my tracks isn’t just the landscapes or the meals—it’s how fully everyone is smiling.
It’s in these smiles that I can relive the highlights as clearly as if I was still there:
The giggles from across the pool as Alexis’s younger sister wrecked Ffej at drinking games.
The wiffle-ball precision of back-and-forth The Wire references at the dinner table.
The childlike wonder on Kevin and Lauren’s faces when the humpback whales launched skyward.
Back at home, I felt all of this over and over again—the gratitude, the love, and the surprisingly painful and shockingly instant nostalgia, hitting me like a rogue wave.
Sometimes, when I’m feeling stuck in life, my brain delivers an epiphany that feels both profound and completely useless.
Recently, it occurred to me that Natasha Bedingfield’s two biggest hits—Unwritten and These Words—are both about the same thing: the euphoric and empowering rush of overcoming writer’s block. They’re about letting yourself move forward, even when you don’t quite know where you’re going. Maybe this struck me because that’s what these perfect yet fleeting weekends really teach you. You can’t hold onto them too hard— you can only let them propel you forward.
Atleast, that was the headspace I was in as I biked to meet Kris for dinner the Friday after the bach party. Alexis was visiting her parents, so I had the night to myself. After a meh week of work and laundry, I prescribed myself friend time. We caught up over grilled broccolini with homemade chili crisp, then walked to Kingfish to watch the Warriors play the Kings. Hannah had just moved into a beautiful loft down the street and joined for the second half.
I wasn’t drinking that night—still recovering after Mexico—but as we sat at the bar, I realized I didn’t need to. Because real friends—the kind who help plan secret proposals and design custom shark hats—are the ones you don’t need a Tecate to talk to for hours.
On my ride home, I passed by my old apartment, where I spent most of my twenties living with Kevin, Tonio, and Matt Rowett. Matt still lived there. And sure enough, the living room light glowed warmly against the February chill.
I didn’t stop in.
But knowing I could was enough.
