Marry Me? I Spent $150,000 On This Proposal

When Sienna Jeffries walked into Glasshouse Chelsea on Aug. 12, 2023, she didn’t think she’d leave the Manhattan event space as an engaged woman. After all, her then-boyfriend Stephen Mensah told her that they were attending his mentor’s party. (“He actually created a fake invitation for it,” Jeffries says.) But when the couple finally made it up to the venue’s 21st floor, she was surprised to learn that she was the guest of honor.

Jeffries and Mensah’s families proudly stood on each side of a rose-petaled aisle, which led to an altar made with sculptural bunches of pink roses and glass-enclosed candles. A neon sign that read “You & I Forever” hung in front of floor-to-ceiling windows as Mensah got down on one knee with a nearly 4-carat diamond ring from Tiffany & Co. and asked Jeffries to be his wife. (After dating for 5 years, the answer was a resounding yes.)

Mensah hired a photographer to capture the sentimental moment, while a DJ spun a mix of American and Nigerian songs as the couple celebrated their lifelong love over cocktails and canapes. Later, Mensah took Jeffries outside for one last surprise: her very own matte black Mercedes-Benz G-Wagon with red interiors.

“It was just magical,” Jeffries says. “He clearly had a vision of certain things that he wanted just based off of Instagram posts that I've sent him years ago.”

Mensah might’ve had the vision — “I just wanted to do something to show how happy I am to have such a wonderful queen by my side,” he says — but he didn’t plan the day alone. Standing on the sidelines to make sure the big night went off without a hitch was Neha Gupta, founder of a Los Angeles-based proposal planning company called Party of Two.

“We started super bright and early at 7 a.m. to get everything set up,” Gupta shares. “We had furniture coming in. Decor, florals, candles, rose petals — everything.” (While Mensah purchased the G-Wagon and hired a driver to bring it there, Gupta completed the surprise with sparklers and a big red bow.)

As the act of getting engaged has become bigger, bolder, and more Instagrammable than ever before, proposal planners have stepped in to create unforgettable events. What was once an intimate moment for two now includes a photographer… and a videographer… and a florist… and a string quartet. At the helm of the big surprise is the planner, who manages all vendors and often designs the event from scratch. According to Michele Velazquez, who co-founded The Heart Bandits and plans 70 to 100 proposals per month, most people enlist planners for their creativity or convenience.

“[Clients] would like a once-in-a-lifetime experience and memorable proposal,” explains Riley Canty, CEO and owner of The Yes Girls, who cites social media as a driving force behind the rise of extravagant proposals. (She has a point: It doesn’t take that much scrolling to find a proposal akin to Alex Cooper’s illuminated engagement or Kourtney Kardashian’s big, beachfront moment.)

“They either need some creative guidance or know how they want to propose, but don't have the time or resources to plan it themselves,” she explains. Most planners start the process by getting to know the couple: Canty sends her clients a detailed questionnaire about the couple’s love story and tastes, while Gupta often asks for a special song “to feel the vibe.” From there, planners typically present their clients with a few design concepts based on their budget and aesthetic.

Just like diamonds, proposal planners operate best under pressure.

Most proposals need to be planned well in advance: Gupta accepts clients up to a year out, but once coordinated an engagement in front of the Bellagio fountains within six hours, complete with candles and a pink floral installation.

Leading up to the big day, planners stealthily talk to their clients via email or direct message to not spoil the surprise. While conversations are often logistical — Canty says she handles correspondence with all vendors, but reaches out to the clients for purchase approval — planners also provide their two cents on the aesthetics. To mirror his fiancée’s vision board, Mensah had originally asked for a sea of red flowers; however, it was Gupta who encouraged him to reconsider the color palette.

“The whole room was already gray and white, and what happens with red is it gets swallowed into those colors and it turns almost black,” she explains. “It doesn't look bright and beautiful and it doesn't translate correctly into a photo. Pink brought out all the colors in the room and looked so magical with the uplighting.”

Once the big day arrives, it’s officially showtime. Sometimes, that means creating a faux aisle with glass-enclosed candles or playing ringmaster to a circus-like assortment of vendors. When Jessica Elkins hired Gupta to plan the perfect proposal for her partner Taylor Elkins during a trip to Cancún, that also meant crossing international borders.

“She stayed at the same hotel as us and was able to assist all vendors with getting to the hotel, getting them set up, and coordinating with the hotel coordinator as well,” Elkins says. “She was in charge of it all; my job was to show up basically.”

Gupta even escorted her now-wife to a “private dinner” so she could be waiting at the proposal site. “I should receive an Oscar for acting,” jokes Gupta, who has planned over 500 proposals since opening Party of Two in 2020.

Despite months of prep work, some proposals don’t go according to plan. Gupta organized one in Las Vegas that was almost foiled by “monsoon winds“ that broke a lot of the decor. However, she was able to lean on her network of vendors to ensure the engagement went off without a hitch. After all, just like diamonds, proposal planners operate best under pressure.

“The job of an experienced proposal planner is to think about everything that could go wrong before it goes wrong, and plan accordingly,” Velazquez says. “If something totally left field happens, [they] can keep calm and handle anything that arises.”

Planning a proposal down to the very last details is a labor of love, but at what cost? Well, it depends. While Canty of The Yes Girls requires a minimum budget of $5,000 for custom clients, she recently planned a $150,000 proposal. Meanwhile, The Heart Bandits’ Velazquez worked on a travel-inspired proposal that totaled around $70,000.

“The concept was ‘jetsetter,’” Velazquez explains. “We wanted to highlight some of the places that they had been to over their relationship.” To do so, The Heart Bandits team created a “petite Paris,” complete with an Eiffel Tower made with moss and lights; a miniature Venice that featured a rose-filled gondola; a rare, Mexico-inspired bag by Christian Louboutin; and a stack of vintage Louis Vuitton luggage.

“Lastly, he walked her over to the pool, where we had placed a sign at the bottom that asked her to travel with him forever,” she adds. “They celebrated with a private rooftop dinner [overlooking New York City.]”

But according to Amy Lynn Parmar, lead planner at New York-based firm Poppy + Lynn, planning a great proposal doesn’t always involve a big budget or an over-the-top production.

“A lot of people still value having an intimate, private moment and will opt for somewhere with great scenery,” explains Parmar, whose proposal planning services start at $1,500. “At the end of the day, this is such a personal moment between you and your partner, and it should feel true to you.”

Parmar took that exact approach when she helped Arielle Martel plan the perfect proposal for her partner Kristina Villarini in 2022. Martel wanted to plan an engagement that represented their love story without breaking the bank. Since Villarini loves to visit New York’s famous Coney Island, Parmar planned a post-proposal picnic with bacon, egg, and cheese sandwiches and champagne.

Not only did Parmar bring fancy stemware, but she also dreamed up the perfect ruse to lure Villarini to the right spot and also created colorful floral arrangements. “Something that would've cost $150, she did it for $25,” Martel says of the florals.

By extravagant proposal standards, this one was rather simple: an engagement without copious candlelight or luxury cars. Yet, Martel and Villarini felt it was authentic to their love — and isn’t that the point?

“I think Amy really made me focus on Kristina instead of thinking about it as a proposal,” Arielle said. “At the end of the day, my girl is a bacon, egg, and cheese girl.”