TV & Movies

What It's Really Like Being a Proposal Planner

In our 9–5 series, we ask our favourite boss babes what a day in the office entails. This week, professional proposal planner Vanessa Ortali, founder of custom event company A Man’s Pursuit, gives us a glimpse into her (romance-filled) grind

proposal planner

Age: 29

Education: Undergraduate degrees in biology and business from Western University

Length of time at current gig:

We created A Man’s Pursuit nine months ago and officially launched the website six months ago, but I’ve been unofficially helping people coordinate proposals and events for years.

What made you want to start your own business?

I have always been an entrepreneur. When I was a kid, my parents came up to me after Easter and asked where all my brother’s chocolates had gone. I had sold it to the neighbours in a raffle and come back with all this money.

Why proposals?

I love love. I didn’t even get into it because of events. I don’t even consider myself an event planner—it’s the love that does it for me.

So what exactly does a proposal planner do?

It’s kind of the same thing as having a wedding planner or a personal assistant. It doesn’t mean that the men can’t do it themselves, it’s that they really want to do a great job. It’s really about filling in the details, like making sure there’s a backup plan and making sure that the girl doesn’t find out, so it can be perfect for her. [As of yet, Ortali hasn’t had any female clients.]

Why do you think guys need a bit of help planning the perfect proposal?

I think it’s natural. A lot of women have big expectations for the proposal and put pressure on their boyfriends, so the men get nervous. I’d say half of our referrals actually come from women giving our information to their partners.

Who are your typical clients?

They’re all business professionals, that’s for sure, and they usually live in cities—some in Canada and others in the U.S. including New York, Miami, Chicago, Boston and parts of California. For proposals, they’re usually between 30 to 40 or 45.

What’s the key to planning the perfect proposal?

It’s really important to understand the woman so I ask a lot of questions about who she is and what she wants. Sometimes we also get a friend or family member involved to make sure that we get it right.

What’s your typical workday like?

I really just plan my schedule around my meetings, but it’s definitely not 9 to 5, and that’s what I like about it. Because I’m always meeting people, I have a lot of my meetings after work hours, but that also means I have the flexibility to wake up at 10 a.m. or not set an alarm in the morning.

How do you get into the zone before going to work?

When you’re an entrepreneur, your businesses can only be as good as you are. So I spend the first two hours of my day doing meditations, gratitudes, visualization and reading to get my mindset right for my day.

What types of proposals have you planned?

I’ve done everything from a proposal at home to the helicopter or private jet to the racetrack. A lot of my job is helping with little details, like making sure her nails are done or that you have a photographer ready or that there’s a little celebration with the friends and family afterwards. We plan how she’s going to feel from the moment she wakes up until she goes to bed.

proposal planner

What are some of the most unusual things you’ve been asked to facilitate?

One of the first questions I ask my clients is, “How do you want her to feel on the big day?” Sometimes the men really want her to be shocked and never see it coming. I’ve also been asked for her to be mad at the groom and or frustrated at the situation. In those scenarios, we have purposely staged issues such as being late, initiated a fight, a fake injury, so she is running home from work thinking she’s going to find an injured boyfriend—or a fake arrest. Nothing gets the heart pumping like a fake arrest.

What are some unique things you’ve incorporated into proposals?

One of the men we worked with brought his girlfriend to an outdoor theatre on the lakefront at sunset and surprised her with an animated short film showing how they had fallen in love, along with her favourite celebrities reading messages of his favourite memories and his love for her.

How many proposals have you planned to date?

Twenty-two so far and a lot of other special events like birthdays, [celebrations for] new moms and anniversaries.

Have you ever had a girl say no to the proposal?

No, we haven’t. [Laughs] Some clients say that we should change our slogan to “Guaranteed yes.”

What was one of the most memorable proposals you’ve helped with?

It’s kind of a simple one, but it’s nice because of the thought that went into it. It was for a corporate woman. She worked really hard, so we got her boss to send her to the spa for an afternoon manicure, massage and hair appointment. She came home that night and we had gotten a stylist to put together the perfect outfit with shoes and thousands of dollars of rented jewellery. At that point she kind of knew she was going to get proposed to. A car picked her up, and took her to a rooftop and where her boyfriend was waiting and he proposed. Then the two of them had a four-course meal on the roof, while a string quartet played—and they danced, which was so cute and endearing. When they went home, their place was filled with rose petals and his speech was printed off so she could have it as a keepsake. For me, it was very intimate, but it was still very glamorous and special. That was one of the first ones I planned, so it was really memorable.

What are some added touches that can make a proposal even more special?

It can be nice to commemorate someone who has passed away or something that the couple has endured together, like an illness. Sometimes it’s lighting a candle, having something engraved, giving a gift, planting a tree or naming a star in honour of the person, or just including it in his speech. It really depends on the couple. I’ve lost my mom, so to me, things like that would make it feel really special.

What are some challenges you encounter?

The weather can really be an issue, but that’s why we always have a backup plan. Sometimes things can be stressful because of timing, like if she’s running late. But, that’s one of the best things about our services: if she’s late or not feeling well or has to take off on a last-minute business trip, which has all happened, we’re the ones that fix everything, not the groom.

How has working on proposals changed how you envision getting engaged?

For me, it’s not so much about the proposal as it is about giving people those memories—whether that’s going on a hot air balloon, a private helicopter, or a shopping spree. It’s just creating that moment and showing people how special they are. It’s not just about the dream proposal; it’s about dreaming a life for yourself. Now, with the people that I’ve met and worked with, I really believe that anything is possible.

What’s your favourite part of the job?

Hearing everyone’s story. It really shows the power of the world and how it brings two people together. It blows me away that, for instance, two people who met years ago and weren’t interested, can then end up sitting next to each other on a plane. How does that even happen?

What attributes do you need to work in this industry?

Flexibility. When you own your own business, it will continuously change based on the people you meet and what clients want. There’s just so much you can’t control. You have to let things naturally evolve over time.

After a long day of proposal planning, how do you unwind?

I love romantic films. If I’m in a bad mood, I’ll watch wedding proposals and how people met on YouTube. It just gives me faith that everything will work out.

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