There are people who love white lace and country clubs. And then there’s Jen Benson.
When Jen set out to plan her own wedding, she knew exactly what she didn’t want. “We didn’t want anything traditional,” she says. “But finding people in the wedding industry who actually understood that was tough. It felt like we were constantly fighting against this rigid, traditional mold.” Where were the weirdos? The offbeat ideas? The weddings that actually looked like the people getting married?
Instead of settling, Jen created something entirely new: Hitched AF, a no-rules, anti-checklist, joy-first wedding planning business for the rebels, romantics, and rule-breakers. “I’m not here to do what’s always been done,” she says. “I’m here to do what feels right.”
Her own way, from day one
Jen’s own wedding looked nothing like a Pinterest board—and that’s exactly the point. She dragged the most expensive dress she’s ever worn through the streets of downtown Las Vegas. Her guests came in wild outfits, feasted on hot dogs and breakfast food, and kicked off the night with karaoke instead of a slow dance. “Our first song was ‘Love is an Open Door,’” she laughs. “It was perfect. It was the best night of our lives.”
Her world is one of bold colors, playful chaos, and deeply personal choices. “I’ve always been a go-against-the-flow kind of person,” she says. And now, she brings that same energy to every wedding she plans.
A career that never fit the mold
Before she was a planner, Jen was a high school counselor, then a lobbyist, then a lawyer. “Each time someone asked, ‘What do you want to be when you grow up?’ I had a different answer,” she says. “Not because I didn’t want to do anything—because I wanted to do everything.” She fondly recalls that growing up, she dreamed of dazzling on a Broadway stage or high-kicking as a Rockette.
Eventually, she landed in law school, motivated by a desire to change the system from the inside. “But once I got in, I realized how hard it is to move the machine,” she admits. “It didn’t feel like I was making the difference I thought I would.”
Planning her own wedding changed everything. “It woke up this part of my brain I hadn’t used in years. I realized—this is it. This is what I’ve been chasing.” And looking back, she can see it now: every job she’s ever had involved some element of planning, organizing, and pulling people together to make something special happen.
Making weddings feel like people
Wedding planning activates both sides of Jen’s brain—the creative and the analytical. A self-professed spreadsheet nerd and vintage treasure hunter, she’s just as happy color-coding a logistics doc as she is styling a tablescape out of flea market finds. “I once spent an entire day driving around town looking for retro suitcases for an aisle installation,” she says. “And honestly? It was one of my most fun workdays ever.”
She’s known to go all in—whether it’s sourcing the perfect vintage salt and pepper shakers or building a floral installation at 3am. And when things go sideways (as they always do), her counseling background kicks in. “There’s something that goes wrong at almost every wedding,” she says. “Being calm, solving problems, and taking care of my couples—that’s my job.” Whether it's a shuttle that never shows, a flower that falls apart, or guests that need wrangling, Jen is the one you want in your corner. And the weddings she creates? They’re as true to her clients as they are unforgettable.
Start with the couple, not the checklist
Jen’s weddings don’t start with a venue or a moodboard. They start with a question:
“Forget everything you know about weddings. Now, tell me—what do you want?”
“Most people don’t even know how to answer that at first,” she says. “They’ve been so trained to follow a formula. But once they let go, that’s when the magic happens.”
She gravitates toward unconventional venues and offbeat collaborators—people and places that reflect the couple’s true essence, not just industry trends. “I want your wedding to feel like you,” she says. “Not like a styled shoot. Not like a Pinterest board. Like you.”
That means every vendor, every space, every detail is chosen with intention. “When we get it right,” she adds, “it doesn’t just look good—it feels right.”
Show up as yourself
Since founding Hitched AF, Jen has dropped the “professional work mask” she wore throughout her career in government and law. She shows up exactly as she is: quirky, intuitive, wacky, and wildly good at what she does. “I call myself the ‘wacky aunt’ of weddings,” she laughs. “Part fairy godmother, part rule-breaker.”
Jen is also neurodivergent—and proud of how her ADHD has shaped her approach. “My brain is wired for interest,” she says. “That means I find almost everything about wedding planning activating. I don’t get bored. I stay sharp.” Diagnosed later in life, Jen had to build systems that worked for her brain long before she had language for it. “I’m a master of a spreadsheet,” she grins. “I love a spreadsheet.”
She also finds that her neurodivergent clients often gravitate toward her. "It's important to truly understand the people you're working with and working for," she says. "Relating to them on a personal level can make all the difference. And even if you don’t share the same experience, knowing how people’s brains work and how they approach big projects like weddings is key to offering the right support." That empathy, paired with her systems and creativity, makes Jen a powerful advocate for every client—especially those who’ve felt like they didn’t quite fit the wedding mold.
Redesigning the industry, one rule at a time
Jen’s mission isn’t just to plan beautiful weddings—it’s to make the industry better.
When I ask about her biggest pet peeve, she doesn’t hesitate: “The extreme genderedness of everything,” she says. “It’s overly heteronormative, and it leaves so many couples—especially queer couples—feeling unseen.”
To help fix that, she co-founded the Queer AF Wedding Expo, a celebratory, inclusive space where queer couples can connect with affirming vendors. Most expos still center the word ‘bride.’ This one starts with champagne and drag performances.
She’s also rethinking what weddings cost—not just in money, but in materials. Her pop-up chapel project offers a more affordable, lower-waste wedding format that still feels special. “Not everyone wants—or can afford—a 200-person wedding,” she says. “But that doesn’t mean they don’t deserve something meaningful and beautiful.” She’s currently working on a relaunch of the pop-up chapel, refined and ready for even greater impact.
Why follow the rules when you can write your own?
As I wrap up my chat with her, one thing's become clear to me: Jen doesn’t wait for permission. That's just how she moves through the world. She doesn’t ask whether the industry is ready. She simply builds what she wishes had existed when she was planning her own wedding—and invites others to do the same.
I ask Jen to describe Hitched AF in three words.
She pauses for just a moment, tilts her head, then grins: “Fun, weird, and inclusive.”
