Paulina Porizkova's engagement ring went missing mid-proposal – here's how her wedding turned out

Czech-born, Sweden-raised supermodel Paulina Porizkova had a feeling comedy writer Jeff Greenstein was just her type before their very first date. The pair originally connected on a dating app in January 2023. “Already this story is ridiculous: why would a stunning former supermodel swipe right on a gawky, bald comedy writer with a disastrous dating profile?” Jeff jokes. “Well, it turns out that as bad as my profile was, I’d chosen a great song for its soundtrack: ‘Modern World’ by Jonathan Richman and the Modern Lovers.” Paulina shared she was a fan, and the two began texting and discovering more common interests. “Soon we’d progressed from texting to FaceTime, from cups of tea to shots of tequila, and the conversations got longer and longer. Until finally – clearly exasperated I wasn’t making a move – Paulina texted, ‘On paper, you’re kind of my perfect man. So when are you coming to New York?’”

Exactly a month after they matched, Jeff made the trip to the city and the two met for drinks at the Hotel Chelsea. “The sight of her in person took my breath away,” remembers Jeff. “And then a mere 10 minutes later, just after our martinis arrived, she kissed me. Our chemistry was off the charts.” He continues, “We spun through dinner, she took me home with her, and we’ve been together ever since.”

In the summer of 2025, the couple was in the spa city of Karlovy Vary in the Czech Republic while Paulina shot a movie. During these two months, Jeff came up with a perfect proposal plan. “I’d found a ring – Czech-made, 100 years old, and Art Deco with a unique cut of diamond optimised to glow under candlelight,” details Jeff. “I found a wooden music box that played ‘The Moldau’ by Czech composer Smetana as a tiny boy popped up with a rose, and I’d found the ideal spot: Goethe’s Lookout, an 18th-century brick tower with a breathtaking view of the city.” He planned to take Paulina there after the movie’s wrap party for the big surprise.

Unfortunately, the party ran late, and Jeff had to frantically drive for them to arrive before the lookout closed for the night. “We get to the tower, I grab the music box, shove it in my pocket, and drag her up five flights of stairs,” he recalls. “We catch our breath. The moment is perfect; the view, stunning. I get down on one knee, say the words, and she says yes. I open the music box, the song plays, the boy pops up with the rose...and there is no ring.” They ran back down to the car as Paulina suggested: “Did you buy it with American Express? Because they have purchase protection.” Thankfully, the ring was back in the car at the bottom of his bag, and it made its way to Paulina’s finger.

The couple’s post-engagement trip around Europe led them to their future wedding venue: Villa Crespi in Orta San Giulio, Italy. Paulina first visited the 19th-century Moorish Revival hotel for a photoshoot 30 years prior and came back to visit with Jeff in 2024. “As we made our way through Germany and Switzerland to Italy, we had the same thought at the same time: ‘why don’t we swing by Villa Crespi and see if we can get married there,” shares Paulina. “It’s an incredibly romantic location no one seems to know about. Uh, until now.” The couple chose July 3, 2026, as their wedding date – exactly three-and-a-half years after their first meeting in New York.

The pair took on planning the celebration entirely themselves, complete with a ceremony at a lakeside town hall followed by a reception at Villa Crespi. “We do, however, have to thank Chiara Ferrari at Villa Crespi, who was immensely helpful in connecting us to local vendors: a florist, a DJ, and so forth,” notes Paulina. The couple kept things relatively simple for their intimate celebration. “Second weddings are different,” says Jeff. “Neither of us wanted to fuss over save-the-dates or set up a wedding website. But, I did want proper paper invitations.” So, the groom asked his graphic designer brother to craft their stationery based on the colors of their venue and the Art Deco aesthetic of Paulina’s engagement ring. They also asked guests to dress formally, but with a hot Italian summer in mind. “Thanks to the colorful paper parasols our friend Jacquie thoughtfully provided, we would say the overall effect was quite Fitzgerald-y,” says Paulina.

One of the hardest parts of planning was actually making sure they could get legally married in Italy – a task many non-residents skip due to all the paperwork. “People kept asking us, ‘Why not do a symbolic ceremony in Italy, then the legal part back in the U.S.,’” says Paulina. “Well, for one, there’s something romantic about having to work for your marriage. And two, we wanted to walk out of our ceremony truly and legally married. But man, did we have to jump through some hoops to get there!”

When it came to finding the perfect wedding dress, Paulina was also ready to put in the work. “I knew I wanted a dress made from scratch; not something off the rack,” the bride shares. “Early on, I hit on the idea of using House of Gilles couture.” She knew Chloe Mendel Corgan – who co-founded the brand with her father, Gilles Mendel – through her son and reached out to collaborate on a look. From the start, Paulina was adamant that she did not want to wear white. “Not, as you might think, because of the virginal connotations – more because I’d worn so many white bridal gowns as a model,” the model says. “I wanted the colour to be sort of a not colour. Something ineffable and elusive, so you couldn’t say ‘she wore a yellow dress’ or ‘she wore a pink dress.’” Paulina also wanted a gown that would “move like water around me.”

The bride gave Mendel photos of Lauren Hutton’s Halston dress from the 1975 Oscars and Grace Kelly’s blue dress in To Catch a Thief as inspiration, alongside a photo of Villa Crespi. The designer sent back a few sketches that captured her vision, with a deep plunge neckline, a cinched waist, and a gauzy pleated fabric in a soft, cool tone. “In fact, at the wedding reception, one of our guests came up to me and said, ‘I’ve recently been taking recreational ketamine, and your dress is the color of element.’ Meaning a colour that cannot be described, like water, which has a colour beyond colour,” says Paulina. “So I guess I got what I wanted!”

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The bride kept her accessories relatively simple. She had the House of Gilles team design a coordinating veil – a dramatic touch requested by Jeff – and wore a simple flower made from the same fabric in her hair. “For jewellery, I wore two tiny teardrop earrings my sons gave me for my 60th birthday last year,” she adds.

Jeff admits he needed some guidance to find his wedding day attire. “When Paulina met me, I typically wore the comedy writer’s uniform, jeans, and logo T-shirts. I’m not even sure I owned a decent suit,” he says. “So I needed a great deal of help.” Stylist Sean Spellman advised the groom to have a bespoke suit made to perfectly fit his 6’7” frame. He guided Jeff towards a classic silhouette in blue wool fabric. “Wearing wool in 90-degree heat seemed insane to me, but he was right. It looked crisp, sharp, and classy,” shares Jeff. “As for the rest of the outfit: I bought a pair of Church’s black oxfords which cost more than my first car, suspenders because they keep your pants from falling down when you’re dancing like a maniac, and I wore my cherished gold 1946 Rolex Oyster Perpetual bubbleback.” He adds, “Watch nerds will know what I’m talking about.”

The wedding weekend began with a casual dinner for guests to get to know one another at a trattoria Pan&Vino in the center of Orta San Giulio. “We fell in love with this place on our very first trip to Orta, perhaps because of the signs out front which warn ‘no pizza, no pasta, no panini,’” shares Paulina. “Also, they have an entire menu page of tinned fish, which stole this Czech girl’s heart immediately.”

The wedding day arrived, and guests gathered at the lakeside garden patio behind the town’s city hall. Unfortunately upon arrival, the bride realized she had left her bouquet back at the hotel. “Two of her friends began frantically pulling flowers out of the ground and assembling one, trying to avoid the watchful eye of Roberta Mattioli, the city official who’d be conducting the legal part of the ceremony,” remembers Jeff. “To Ms. Mattioli’s enduring credit, she made no move to stop them.”

Paulina’s sons and stepson played “The Moldau” by Smetana on violin and guitar as the wedding party made their way down the aisle. Jeff’s sister Jill and Paulina’s brother Kym served as officiants for the ceremony, but also wrote vows for the couple. “We left it entirely to Jill and Kym, who sent drafts back and forth from Maine to Texas, and they were magnificent,” shares Jeff. “We wouldn’t change a word – and coming from two writers, that’s saying something.” Adds Paulina, “For me, family is my sense of safety, so having family walk us through the vows was profound.”

At the end of the ceremony, Jeff stomped on a glass, and the newlyweds kissed at least four times before recessing to “Go All the Way” by The Raspberries. They completed their brief civil ceremony to complete their legal marriage, and had the song blasted one more time over the speakers. Instead of taking traditional portraits afterwards, the couple did one big group photo with all their guests on a cobblestone street.

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The party moved to Villa Crespi for dinner, toasts, and lots of dancing. The hotel’s chef, Antonino Cannavacciuolo, has earned nine Michelin stars, so naturally, “many people said it was the best wedding dinner they’d ever had,” says the bride. There was a creative flair to the reception as well. Each table was named after famous Italian directors – and one Czech director, Miloš Forman, the late husband of one of the guests. “Our first dance was ‘Moon River,’ another song that’s very meaningful to us,” shares Paulina. “A line from that song was on the card accompanying the flowers Jeff sent me after our first date.” While there was only one planned speech by Jeff’s son Henry, others – including the groom’s brothers, Paulina’s sons, and her mother – took the mic for meaningful toasts. “Then Jeff made a speech that if I were not already madly in love with him, I would have fallen madly in love with him,” says Paulina.

Dancing followed with an impromptu Jewish hora to “Don’t Stop Me Now” by Queen. There was also a Czech tradition that took place. “Halfway through the reception, Eron Otcasek – my new 53-year-old stepson – informed me my bride was being held hostage at a bar across the street,” says Jeff. “Henry accompanied me to the bar, packed with Argentinian football fans who were watching the World Cup. I’d forgotten my wallet, so Henry paid the 55 euro bar tab ransom while a pair of Argentinians drew their flag on my face.”

As the reception came to a close, the couple cut into a cake topped with the same figurines from Jeff’s parents’ wedding cake 63 years prior. “I smashed two pieces into Jeff’s mouth, and he was silent for perhaps the first time in our relationship,” shares Paulina. “Then we made our way up to our hotel room, where – yet another Czech tradition – all the furniture had been piled onto the bed. The thinking is that unwrecking the room teaches the new couple a lesson in cooperation right at the start.”

Reflecting on the weekend, the newlyweds say, "We’re warmed by feeling we got exactly the wedding we wanted – no notes – and exactly the partner we’ve always dreamed of.”