There are people who love white lace and country clubs. Then there is Jen Benson. When she set out to plan her own wedding, she knew exactly what she did not 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, she built something 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 wedding looked nothing like a Pinterest board, and that is the point. She dragged the most expensive dress she has ever worn through the streets of downtown Las Vegas. Guests came in wild outfits, feasted on hot dogs and breakfast food, and opened 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 bold colors, playful chaos, and deeply personal choices. “I’ve always been a go-against-the-flow kind of person,” she says. Now she brings that 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 I wanted to be when I grew up, I had a different answer,” she says. “Not because I didn’t want to do anything, because I wanted to do everything.” Growing up, she dreamed of a Broadway stage, or high-kicking as a Rockette. Eventually she landed in law school, hoping to change the system from the inside. “But once I got in, I realized how hard it is to move the machine. 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.” Looking back, she can see it now: every job she ever held involved some element of planning, organizing, and pulling people together to make something special happen.
Forget everything you know about weddings. Now tell me what you want.
The spreadsheet and the flea market
Wedding planning runs both sides of Jen’s brain, the creative and the analytical. A self-professed spreadsheet nerd and vintage treasure hunter, she is as happy color-coding a logistics doc as 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 goes all in, whether that means hunting the perfect vintage salt and pepper shakers or building a floral installation at 3am.
When things go sideways, and they always do, her counseling background takes over. “There’s something that goes wrong at almost every wedding. Being calm, solving problems, and taking care of my couples, that’s my job.” A shuttle that never shows, a flower that falls apart, guests who need wrangling: Jen is the one you want in your corner. And the weddings she creates are as true to her clients as they are unforgettable.
Jen is also neurodivergent, and proud of how her ADHD shaped her approach. “My brain is wired for interest. That means I find almost everything about wedding planning activating. I don’t get bored. I stay sharp.” Diagnosed later in life, she had built systems that worked for her brain long before she had the language for it. “I’m a master of a spreadsheet,” she grins. “I love a spreadsheet.” Her neurodivergent clients often find her, too. “It’s important to truly understand the people you’re working with. Even if you don’t share the same experience, knowing how people’s brains work, and how they approach a big project like a wedding, is key to offering the right support.” That empathy, paired with her systems and creativity, makes her a fierce advocate for anyone who has felt like they did not fit the wedding mold.
Start with the couple, not the checklist
A Hitched AF wedding does not start with a venue or a moodboard. It starts 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 at first,” she says. “They’ve been so trained to follow a formula. But once they let go, that’s when the magic happens.” From there she gravitates to unconventional venues and offbeat collaborators, people and places that reflect the couple rather than the trend. “I want your wedding to feel like you. Not like a styled shoot. Not like a Pinterest board. Like you.” Every vendor, every space, every detail is chosen with intention. “When we get it right, it doesn’t just look good. It feels right.”
Redesigning the industry, one rule at a time
Jen’s mission is not only to plan beautiful weddings. It is to make the industry better. Ask about her biggest pet peeve and she does not hesitate. “The extreme genderedness of everything. It’s overly heteronormative, and it leaves so many couples, especially queer couples, feeling unseen.” So she co-founded the Queer AF Wedding Expo, a celebratory, inclusive space where queer couples meet affirming vendors. Most expos still center the word “bride.” This one opens with champagne and drag performances.
She is also rethinking what a wedding costs, in money and in materials. Her pop-up chapel offers a more affordable, lower-waste format that still feels special. “Not everyone wants, or can afford, a 200-person wedding. That doesn’t mean they don’t deserve something meaningful and beautiful.” A refined relaunch is in the works.
Since founding Hitched AF, Jen has dropped the professional work mask she wore through her years in government and law. She shows up exactly as she is: quirky, intuitive, wildly good at what she does. “I call myself the wacky aunt of weddings,” she laughs. “Part fairy godmother, part rule-breaker.” She does not wait for permission or ask whether the industry is ready. She builds what she wishes had existed when she was planning her own wedding, and invites everyone else to do the same. Asked to describe Hitched AF in three words, she tilts her head, pauses, then grins: “Fun, weird, and inclusive.”
_Hitched AF is at hitchedaf.com and @hitchedaf_._