Before he ever coordinated a wedding timeline, negotiated a vendor contract, or sketched out an audacious color palette, Rob Anderson spent more than two decades working in higher education, working his way up the ladder from Hall Coordinator to Associate Dean of Student Affairs. For the majority of that time, he lived in a dedicated space in the first year residence halls. “I spent just over 20 years working in that field,” he says of his former career, most of which was spent at small private liberal arts colleges where he admits, his job was more of a lifestyle than a typical 9-to-5. Nevertheless, working in those settings gave him the “opportunity to try on a bunch of different hats, everything from residence life to student affairs and student activities, to orientation and student organizations.”

In those roles, he discovered the foundations of his future career as a wedding planner almost accidentally. Working on college campuses where budgets were lean but expectations high, he developed a personal superpower: Creating beauty with limits. “We didn’t have the budget you might have at a big university,” he explains. “So, when couples come to me and say they want a nice wedding, but they don’t have the same budget that someone else might, I tell them, ‘You’re in perfect hands because I am fully versed in planning diamond-level events on a rhinestone budget.’”

Rob’s undergrad years were spent studying music performance, with an emphasis in voice, but even that training seems prophetic in hindsight. A life saturated in theater and the arts refined his instinct for design, atmosphere, and storytelling. It also honed the interpersonal skills that would be central to his new life.

But after two decades in higher ed, a forced pivot, and then the pandemic, upended his career. Burned out and craving a new direction, he began brainstorming “ideas of businesses that I could start with very little investment.” One idea stuck.

“I decided to take the plunge,” he says, “to take my knowledge from working in higher ed, planning those events, and the counseling education I had in my master’s program, and then couple that with the creativity and background in theater and music. Wedding planning just seemed like a really good fit for me.”

That fit became OSO IN LOVE, the Madison-based wedding planning company that has evolved from a one-person operation into a thriving multi-planner team with an unmistakable aesthetic identity and a cult following among couples who want something different.

Building a New Kind of Wedding Company

When Rob launched OSO IN LOVE in 2021, he knew it would not follow the standard model. “I didn’t want to be just your run-of-the-mill sort of wedding planner,” he says. Instead, he built a one-stop shop: Planning, day-of coordination, design and branding, officiant services, music and entertainment, decor and linen rentals, an entire ecosystem designed to reduce stress and maximize creative control.

Most planners offer only management. Rob wanted to offer meaning.

“Our whole experience is rooted in empathy,” he says. “We’re always going to look at things from a perspective of putting ourselves in our couples’ shoes.” That approach, he says, “is not the norm” in the industry, where logistics often overshadow emotion. But for Rob, coming from a career built on counseling, conflict resolution, and student development, emotion is the job. “This process of planning a wedding is highly emotional,” he explains. “We truly are sort of an armchair counselor.”

This emotional intelligence is one of the company’s signatures. The other is OSO IN LOVE’s design philosophy, which veers far outside the usual white-on-white conventions.

“I gravitate toward out-of-the-box, non-conventional designs,” Rob says. “Bold choices. Things you wouldn’t expect to see at a wedding.” His inspirations come from everywhere: Interior design, architecture, typography, fashion, art. “I may see something and I’ll say, ‘I need to remember that and figure out a way I can flush that out into a realized concept.’”

One of his most memorable creations came, improbably, from a night in the emergency room. While waiting for hours, he stared at the newly refreshed UW Health System logo on the wall. “I was like, ‘God, I really love that. I love the colors.’” That tiny visual spark eventually became a full editorial installation for a wedding expo: A vibrant hybrid of vintage comic books, Roy Lichtenstein, superhero motifs, bold typography, and riotous color. “There was nothing else like it,” he says. “It was so colorful and so bold and not what you would expect to see at a wedding.”

The result resonated. The stationery designer received new bookings from couples drawn to the rebellious aesthetic. The installation’s blog post titled “Holy Matrimony” became one of the most-visited pages on his website.

These bursts of unexpected creativity are what Rob lives for. “It’s like going back to those days of working in music and theater,” he reflects. “Anything’s possible.”

The Grind & the Glory of Wedding Season

Wedding planning may look romantic from the outside, but the job is deeply physical, logistically grueling, and relentlessly seasonal. Rob describes wedding days as “boots-on-the-ground” affairs where his Apple Watch might log “as many as 35,000 steps in a day.” Summer weekends basically disappear for him, and the offseason becomes a period of recovery, strategy, and creative development.

Unexpectedly, Rob found that his new work overlapped his previous experience with campus life in a way that surprised even him. “There are a lot of parallels,” he says. In both worlds, intense on-site periods alternate with calmer administrative months. In both, burnout is real. And in both, success depends on staying grounded in purpose.

For Rob, that grounding comes from the couples themselves, and especially from the couples whose life experiences mirror his own.

Why Working With Same-Sex Couples Matters So Deeply

When the interview shifts to LGBTQ+ couples, Rob’s voice changes. “I’m sorry, I’m starting to cry,” he says at one point. “But as someone who grew up and was bullied and struggled coming out of the closet, it gives me such intense joy to see these couples have their relationships acknowledged.”

His connection is visceral and personal. “There aren’t a lot of big differences between working with a straight couple and a same-sex couple,” he explains. “But there are some nuances, and it’s that shared experience that a straight business owner is not able to provide.” He understands the potential micro-pressures, the emotional history, the family dynamics, the fears, the longing for affirmation.

When an LGBTQ+ couple hires him, he says, “It feels like you’re at home.”

That sense of community extends to the vendor team as well. “Typically, they want to support members of the community who are providing services,” he says. The result is a celebratory feedback loop of queer couples connecting with queer vendors, each affirming the other’s craft, identity, and story.

There is also an educational element when non-LGBTQ+ vendors participate. “It’s an opportunity to help educate that person and make them aware of what it takes to work with diverse couples,” he explains. Whether it’s pronouns or gender-neutral restrooms, Rob steps effortlessly back into his educator role, happy to bridge gaps and expand understanding.

This is work he would do full-time if the market allowed it. “I wish my bread-and-butter could be just working exclusively with same-sex couples,” he says. “It’s something that’s really important to me.”

A Growing Team, A Growing Vision

From a one-man operation in 2021, OSO IN LOVE has expanded rapidly. “We went from a team of one to a team of two, to a team of three, to a team of four,” Rob says. For 2026, they’ll be a team of six. His planners include former interns, longtime assistants, and even former brides and grooms, all people who saw his work up close and wanted to be part of it.

The company now handles nearly 50 weddings a year. But as it expands, its heart remains deeply personal: Empathy-driven, design-forward, and rooted in the conviction that weddings are about people, not schedules.

Rob’s long-term dream is to focus even more heavily on design, branding, and creative direction. But no matter how OSO IN LOVE evolves, his core philosophy remains unchanged: “We don’t look at couples as just a number. We’re here to help you, guide you, and validate your experience.”

In the end, it’s not just about weddings. It’s about giving people the celebration they deserve, one that is bold, beautiful, unconventional, and true.

HOLY MATRIMONY

Publisher: @wedplanmadison
Coordination & Design: @osoinloveevents
Floral: @the_cosmic_gardens
Cake & Desserts: @sandykakeswidells
Stationery & Signage: @lkbridal
Suits: @menswearhouse
Rentals: @velvet_rentals
Balloons: @daydream.design.co

LOVE DEFIES GRAVITY

Publisher: @wedplanmilwaukee
Concept, Coordination & Design: @osoinloveevents
Venue: @turnerhallmke
Photography: @reminiscephotography
Videography: @boxcarphotography
Gaffer: @life.likecamera
Stationery & Signage: @lkbridal
Florals: @f4dweddings
Fashion: @missrubyboutique
Suit: @duboisformalwear
Hair & Makeup: @melissaannartistryco
Rentals: @eventessentialsmadison
Cake: @cowboydavids
Models: @therockagency, @jpapillion15, @allisonrath