Thinking of proposing in a restaurant? Chicago chefs have some thoughts for you

Chicago Tribune

12-02-2025

This time of year, romance and all its seasonal trappings are everywhere — heart-shaped candy boxes and cuddly teddy bears, anyone?. But while Valentine's Day comes only once a year, true love isn't limited to one day.
The same limitless scope can be said of restaurant wedding proposals. From a casual pizza joint along the Chicago River and a two-Michelin-starred fine-dining spot to everything in between, saying 'I do' is as popular as ever at Chicago restaurants. So popular, in fact, that one restaurant has created its own proposal package.
At Uptown's Cariño, Executive Chef/partner Norman Fenton is very particular about every aspect of the fine dining restaurant. That includes the Spanish-language playlist at the Michelin-starred spot, which features a modern take on Latin cuisine. But he recently acquiesced to a music request during the restaurant's late-night taco omakase. And for good reason — the customer was proposing.
'That's the one and only time I ever took a song request,' said Fenton, who recalled the girl's jaw dropping when she heard the song and saw the chef walking out dessert with the ring. 'We wanted to make this guy's night as perfect as it could be.' Fenton is no stranger to the importance of music when it comes to romance. When he proposed to his then-girlfriend in Tulum, he hired a mariachi band to play her favorite song during dinner.
When it came time for Marco Lappo to propose last December, he knew just the spot: West Town's Piccolo Sogno, a favorite restaurant of his and his girlfriend, Alexandrea Rizzo. As a restaurant owner himself, of Pazzi Di Pizza in Elmhurst and Park Ridge, Lappo had some insight on how to make sure everything went off without a hitch.
He opted for the restaurant's private room. 'My fiancée's not one for the whole show but I wanted to do something special for her,' Lappo said.
He also worked closely with Piccolo chef/partner Tony Priolo on the proposal and the dinner for family that followed. The whole staff was in on the surprise, including the valets who parked cars a few blocks away and picked up petals that dropped from the heart-shaped flower decoration in the parking lot so Rizzo wouldn't be tipped off.
Even with all his preparation and insider expertise, Lappo's proposal wasn't stress-free. 'Nothing would have prepared me to getting down on a knee and marking the start of a lifelong commitment with my girlfriend,' he said.
Over its 40-plus years, Mart Anthony's has seen plenty of proposals, said Michael Campo, who along with his brother, Jack, and father, John, owns the West Town restaurant. In fitting with the Italian American restaurant's casual ambiance, complete with wedding photos lining the walls, proposals are often laid-back, including one from a few weeks ago in which the restaurant didn't know it was going down on the patio until after she said yes. Forgoing the typical Champagne celebration, gratis tequila shots at the bar inside followed — the couple had previously attended a special tequila dinner at Mart Anthony's.
Converting the restaurant's tented patio to a cozy heated permanent structure with twinkling lights hasn't gone unnoticed by couples. 'It's really romantic so I guess it's influencing people to propose,' Campo said.
Ambiance also has played a role in proposals at Miru, the elegant 11th-floor Japanese restaurant at the St. Regis Hotel offering beautiful views of Lake Michigan, Navy Pier and the Chicago skyline. 'During this past year, we've seen a bump up in elaborate proposals with extravagant décor,' said Allison Gallese, partner at Miru and neighboring Tre Dita. Gallese oversee events at both restaurants.
After half a dozen of them, Miru decided to build its own proposal package. Starting at $1,500, it includes one hour of private access to the terrace, a candlelit aisle framed by a floral archway and a sparkling wine toast. A complimentary sabering of a bubbles bottle, a St. Regis tradition, is included for those who want some extra excitement. A photographer and other embellishments are available as add-ons.
'Generally, men are not event planners,' Gallese said. 'They want something beautiful where everything is ready to go and then they can just show up — and they're more than happy to pay for it.'
The proposal at Miru is often followed by dinner at Tre Dita downstairs with family and friends. A couple who got engaged at Miru is now in the planning stages of their wedding at Tre Dita.
'Restaurants are always looking for new revenue streams,' Gallese said. 'This is something we can do outside of our normal business hours that creates lasting memories and repeat customers.'
Since opening in August 2021, Lincoln Park's Esmé has had a couple of proposals, says Katrina Bravo, who owns the Michelin-starred restaurant with her husband, chef Jenner Tomaska.
After receiving an email asking to do something special for a proposal a few years back, Bravo got busy organizing the details. Flowers were set to arrive at the table post-proposal and a time was chosen for the drop-off of the ring, which was promptly put in the restaurant's safe. Early in the multicourse meal, the ring was placed underneath a cloche to look as if it were part of the dish. Glasses of Champagne were at the ready. The couple now return every year on their anniversary and have become part of Esmé's dining membership club.
'It's so special to be part of someone's history and story,' Bravo said.
Or perhaps you're looking for something casual? Streeterville's Robert's Pizza & Dough Co. is no stranger to proposals, especially on its riverfront outdoor patio and spacious dock. Last year they had two on the same day. 'A lot of people have their first dates here,' said Katie Derry, the restaurant's catering and event manager. 'We have a lot of people who are passionate about our pizza.'
One of those couples who went on their first date at Robert's recently got engaged in the restaurant's private dining room, a surprise proposal that Derry helped organize with the boyfriend. 'Love Story' by Taylor Swift played when his girlfriend walked in. Flowers, candles and Champagne were set up on the table. In the middle, a pizza-filled box with 'Will you marry me?' written on it added a personal touch.
Victor Ramos and Martina Gunaratnam had their first date at River North's Sunda in spring 2016. So, when it came time to propose in 2022, choosing a spot was easy for Ramos, especially since he knows the restaurant's culinary director, Mike Morales. 'It was a full-circle moment for us,' Ramos said.
To add to the special occasion, Morales recreated a dish the couple had all those years back. After he dropped the hamachi crudo at the table, the proposal took place, followed by a yes.
'I do' tips
At two-Michelin-starred Oriole, general manager and wine director Emily Rosenfeld highly recommends reaching out beforehand if a proposal is in the works. 'A lot of times, people want us to tell them what to do, but ultimately having an idea of how you want to propose is helpful,' she said.
That's especially beneficial if you're looking for some sort of interactive participation, including placement of the ring. 'There have been times that guests wanted us to hide the ring in the mignardise course,' said executive chef/owner Noah Sandoval. The final course is presented in a ceramic white orb, which is deconstructed at the table with the ring hidden inside.
Because of the West Loop restaurant's open kitchen, Sandoval and his culinary team need to play it as cool as the front-of-the-house staff. 'I have to go around the kitchen and tell everybody to quit staring at them as they're going to know,' he said. 'I have to make sure everyone behaves and doesn't ruin it for them because it's a once-in-a-lifetime thing.'
Paul Solomon, director of operations for Vistro Prime in Hinsdale and Petite Vie in Western Springs, is a big fan of rehearsing what you plan to say, how you will ask, kneeling technique if going that route and how you will be placing the ring on your partner's finger. 'As a recent newlywed myself, coming up with the right way to ask your love interest to marry you is exciting yet complicated,' he said. 'Regardless of where you decide to propose, make sure it is meaningful.'
Equally important is knowing your partner. 'Read your soon-to-be fiancée,' Gallese said. 'Not everyone wants to be the center of attention.'
If he knows ahead of time, La Grande Boucherie Executive Chef Michael Taus puts the couple at a visually pleasing table where they can easily hear each other. He'll also personally congratulate the couple afterward and order them Champagne. 'I'm a sucker for romance,' he said.
Sunda's Morales also suggests contacting the restaurant prior. 'Restaurants will bend over backwards,' he said. 'Everyone loves love.'
When it comes to the food, The Bellevue's executive chef, Russell Kook, recommends the 'KISS philosophy: Keep it simple, stupid,' he said, with a bottle of Champagne and dessert as givens. 'If we can make them want to come back to the restaurant by going a little bit out of our way that's what we do. That's hospitality.'
Mart Anthony's Campo thinks old-school when it comes to proposal food. 'This is an Italian restaurant, so you could do the 'Lady and the Tramp' and get some spaghetti and meatballs.'
One big don't, Taus said, is doing it during Restaurant Week or Valentine's Day. 'If it's on a night that's not so crazy, the restaurant can give you special attention,' he said. 'You don't want to get lost in the shuffle.'
And when it comes to the age-old question of before or after the meal, there are opinions on both sides.
Gallese recommends before the meal. 'For lack of better words, get it over with and then celebrate.'
Bravo agrees. 'I wouldn't suggest doing it with dessert. You will have to sit through this entire meal and inevitably you'll be as nervous as hell.'
But doing so afterward does have advantages. 'I think it's better after so you can get some liquid courage in you,' Kook said.
'Some prefer to pop the question before to enjoy a celebratory meal afterward, while others choose to propose during dessert for a sweet finale,' said Michelle Durpetti, principal at River North's Gene & Georgetti. 'Consider what suits your partner's preferences and the vibe you're looking for.'
Then these days, there's the extra complication of social media.
At Oriole, when a customer asks the restaurant to film the proposal on their phone, Rosenfeld recommends they ask their server to charge their phone as a way to do the hand-off discreetly.
'Years ago, it was more about them coming back and telling their friends,' Taus said of restaurant wedding proposals. 'Now with social media, they are telling the world.'