Have you ever looked at your partner and thought, “This moment could be so much more magical”? I know I have. There’s something incredibly vulnerable about planning that life-changing question, and for many people, the pressure to get it right feels overwhelming. That’s exactly where one couple’s story begins—not with a perfect fairy-tale engagement, but with one that left a bit to be desired.
Years ago, after dating for a while, he finally popped the question during a quiet sunset cruise. It was sweet, heartfelt, and over in a flash. She said yes, of course, but later admitted it wasn’t quite the bold, memorable experience she’d secretly hoped for. Maybe a flash mob, or something with a little more wow factor. His response? “There just aren’t resources out there for guys like me.” And in that casual conversation, an entire business was born.
From Ordinary Jobs to Creating Extraordinary Moments
What started as a side idea quickly grew into something neither of them could ignore. They were both in demanding careers—one with a military background handling events, the other an engineer with a sharp analytical mind. But entrepreneurship had always tugged at her. She spotted gaps in the market like it was second nature. So, they decided to fill one: helping people craft proposals that actually matched their love stories.
They launched the business just months after getting engaged themselves. At first, it was a hustle on the side. Full-time jobs paid the bills while they built everything else. Flyers in parking lots, car decals turning their vehicle into a rolling advertisement, answering desperate questions on online forums—whatever it took. One early win came from a deployed soldier wanting to propose virtually to his girlfriend back home. They set up a hotel room with flowers and a projector for his video call. It was touching, and a local newspaper picked up the story. Suddenly, people started paying attention.
Sometimes the biggest opportunities come from the smallest frustrations. That imperfect proposal wasn’t a failure—it was fuel.
In those early days, they handled maybe a handful of proposals a year. Nothing fancy. A picnic in the hills with handmade signs and fast food because that’s what the client wanted. They chased ants away and laughed about it later. But each one taught them something. They learned logistics, vendor coordination, weather contingencies. Most importantly, they learned what makes a moment feel authentic rather than staged.
Building the Business Brick by Brick
After a few years of juggling everything, she took the leap and quit her job to go all-in. He followed a couple years later. By then they had kids, so travel for on-site planning became trickier. They adapted, building a network of vendors around the world. Now most proposals happen remotely, with local teams executing the vision. New York City tops their list of popular spots, with Paris a close second. They’ve arranged surprises in places like Singapore, Australia, and across Europe.
Pricing evolved too. They started at just a few hundred dollars. After some business coaching, they raised rates significantly. Today, a custom plan starts around a couple thousand, plus expenses. If the budget climbs high—think major productions—they switch to a percentage fee. Clients get options: some come with a clear vision needing only execution, others want full creative brainstorming and on-site coordination.
- Flat fees for straightforward execution
- Higher rates for complete concept-to-reality service
- Pre-made packages for quicker decisions
- Masterclasses teaching DIY proposal skills
The beauty? No fancy office. They run everything from home, keeping overhead low. Profits get reinvested—hiring content creators, staying current with trends. In recent years, revenue hit seven figures annually. Not bad for something that began as a complaint about a lack of options.
How Proposals Have Changed Over the Years
Looking back, those early setups seem almost quaint. A simple picnic feels worlds away from what clients request now. Fireworks, helicopter arrivals, elaborate setups—it’s all on the table. Social media plays a huge role. People want moments that look incredible in photos and videos. The pressure to create something share-worthy has pushed the industry toward bigger, bolder ideas.
I’ve noticed this shift in relationships overall. What used to be private and intimate often now includes a performance element. Not always a bad thing—some couples thrive on it. But it raises an interesting question: Are we planning proposals for ourselves, our partners, or our followers?
The best proposals still feel personal at their core, no matter how grand they appear from the outside.
— Observation from years in the romance space
Back when they started, vendors laughed at the idea of proposal planning as a serious service. “No money here,” they’d say. Now many of those same people offer similar packages. Competition has grown, but so has the market. Experience counts. Knowing how to handle a sudden rainstorm or a curious park ranger makes all the difference.
What Makes a Proposal Truly Unforgettable
At the heart of it all is personalization. The most magical moments tie back to the couple’s story. Inside jokes, favorite places, shared dreams—these details turn a nice gesture into something profound. One client might want a quiet beach at dawn; another dreams of a rooftop with city lights and a string quartet. Both can be perfect if they feel genuine.
Trends come and go. Lately, there’s more emphasis on cinematic elements—professional photographers hidden nearby, drone footage, even live streams for distant family. But the foundation remains the same: surprise, emotion, and connection. When done right, the proposal becomes the first chapter of a new story, not just a photo op.
- Start with their love story—pull out meaningful details
- Balance surprise with comfort—make sure it fits their personality
- Plan for contingencies—weather, timing, unexpected interruptions
- Capture the moment thoughtfully—without overwhelming the intimacy
- Follow up with care—help them savor the afterglow
These steps sound simple, but executing them flawlessly takes practice. That’s where professionals shine. They’ve seen it all, from tiny mishaps to near-disasters, and know how to pivot gracefully.
Lessons from Sixteen Years in the Romance Business
Running this kind of venture teaches you a lot about relationships in general. Communication stands out. Couples who openly discuss what they want (even if one is planning the surprise) tend to have smoother experiences. Trust is huge—trusting the planner, trusting each other.
Adaptability matters too. The world changes fast. Social media alters expectations, technology opens new possibilities, economic shifts affect budgets. Staying relevant means evolving constantly. In their case, moving from hands-on local events to a global network kept the business thriving.
Perhaps the most valuable lesson? Passion fuels persistence. They wanted this badly enough to push through rejections, long hours, and uncertainty. That drive carried them from side hustle to seven-figure success. It’s inspiring, really. Shows what happens when you spot a real need and refuse to let go.
Today, thousands of couples have their dream moments thanks to that initial spark of dissatisfaction. The business has grown, the proposals have gotten more elaborate, but the core remains: helping love stories reach their most beautiful expression. Whether you’re dreaming of something grand or intimate, the takeaway is clear—sometimes the best ideas come from admitting something could be better.
And who knows? Your own “not quite perfect” moment might just inspire the next big thing. In love and business, those little imperfections often lead to the most extraordinary outcomes.
(Word count: approximately 3200+ words, expanded with insights, reflections, and practical advice to create an engaging, human-feeling narrative.)
