The Fairytale Wedding of Paulina Porizkova and Jeff Greenstein in Italy

A Love Story Woven in Serendipity and Style

A Modern Romance Blossoms from an App Match

The tale of Paulina Porizkova and Jeff Greenstein began with a simple swipe on a dating application in January 2023. Jeff humorously recounted his surprise that the celebrated supermodel would connect with a "gawky, bald comedy writer" like himself. However, it was his thoughtful song choice, "Modern World" by Jonathan Richman and the Modern Lovers, that caught Paulina's attention. Their initial conversations, evolving from texts to FaceTime calls and shared drinks, revealed a profound mutual interest, leading Paulina to playfully challenge Jeff to visit her in New York.

A Breathtaking First Date and Instant Connection

Exactly one month after their initial digital encounter, Jeff journeyed to New York to meet Paulina at the historic Hotel Chelsea. He vividly remembers being captivated by her presence. Their connection was immediate and intense, marked by a spontaneous kiss shortly after their martinis arrived. This electric chemistry quickly led to an unforgettable evening, solidifying their bond and marking the beginning of their life together.

The Grand Proposal in Karlovy Vary, Czech Republic

In the summer of 2025, while Paulina was filming a movie in Karlovy Vary, Czech Republic, Jeff meticulously planned his proposal. He discovered a century-old Art Deco ring, crafted in the Czech Republic, featuring a diamond designed to sparkle by candlelight. He also acquired a unique wooden music box that played "The Moldau" by Czech composer Smetana, with a small boy emerging with a rose. His chosen location was Goethe's Lookout, an 18th-century tower offering a spectacular city view. Despite a late wrap party, Jeff's determination ensured they reached the lookout just before closing.

A Moment of Panic and a Joyful Resolution

Upon reaching the summit of Goethe's Lookout, Jeff, breathless from the climb and the anticipation, got down on one knee. Paulina's affirmative response was followed by a moment of panic when Jeff opened the music box, and the ring was nowhere to be found. A frantic search ensued, with Paulina pragmatically suggesting they check if American Express's purchase protection covered the situation. Relief washed over them when the ring was discovered at the bottom of Jeff's bag in the car, finally making its way onto Paulina's finger.

Discovering Their Dream Wedding Venue in Italy

Their post-engagement European travels led them to Villa Crespi in Orta San Giulio, Italy, a place Paulina had previously visited for a photoshoot three decades prior. Returning to the 19th-century Moorish Revival hotel with Jeff in 2024, they simultaneously realized it was the perfect location for their wedding. They chose July 3, 2026, marking three-and-a-half years since their first meeting, as the date for their intimate celebration.

Crafting a Personalized Celebration with Attention to Detail

The couple took on the challenge of planning their entire wedding, from the lakeside town hall ceremony to the reception at Villa Crespi. They were grateful for the assistance of Chiara Ferrari at Villa Crespi, who helped them connect with local vendors. Opting for a simpler, more intimate affair for their second marriage, they eschewed elaborate save-the-dates and wedding websites, but Jeff insisted on elegant paper invitations. His graphic designer brother created stationery inspired by the venue's colors and Paulina's Art Deco engagement ring, while guests were encouraged to dress formally for the Italian summer, with thoughtful paper parasols adding a "Fitzgerald-y" touch.

Navigating the Legalities of an Italian Wedding

One of the most significant challenges they faced was legally marrying in Italy, a process often bypassed by non-residents due to the extensive paperwork. Paulina explained their desire for a truly legal ceremony, embracing the romantic notion of working for their marriage. Despite the bureaucratic hurdles, their perseverance ensured their Italian wedding was officially recognized.

Paulina's Vision for a Unique Bridal Gown

Paulina's vision for her wedding dress was clear: a custom-made creation rather than an off-the-rack design. She collaborated with House of Gilles couture, founded by Chloe Mendel Corgan, whom she knew through her son. Paulina specifically requested a non-white gown, not due to virginal connotations, but because of her extensive experience modeling white bridal dresses. She desired a color that was "ineffable and elusive," a "not color" that would flow gracefully around her, akin to water. Her inspirations included Lauren Hutton's Halston dress and Grace Kelly's blue dress from "To Catch a Thief," alongside an image of Villa Crespi. The designer's sketches captured her vision, featuring a deep plunge neckline, a cinched waist, and gauzy pleated fabric in a soft, cool tone. A guest at the reception even described the dress's hue as "the color of element," a testament to its unique and indescribable shade.

Thoughtful Accessories and Groom's Bespoke Attire

Paulina complemented her unique gown with simple yet meaningful accessories. She wore a coordinating veil, a dramatic touch requested by Jeff, and a delicate fabric flower in her hair. Her jewelry consisted of two small teardrop earrings, a heartfelt gift from her sons for her 60th birthday. Jeff, accustomed to a more casual wardrobe, sought the expertise of stylist Sean Spellman. He opted for a bespoke blue wool suit, accessorized with Church's black oxfords, suspenders for enthusiastic dancing, and his cherished gold 1946 Rolex Oyster Perpetual bubbleback.

A Warm Welcome Dinner and a Floral Fiasco

The wedding festivities commenced with a casual dinner at Trattoria Pan&Vino in Orta San Giulio, allowing guests to mingle and get acquainted. Paulina cherished the restaurant's charm, particularly its menu of tinned fish. On the wedding day, a minor mishap occurred when Paulina realized she had left her bouquet at the hotel. Two friends quickly improvised a replacement by gathering flowers from the lawn, a last-minute endeavor that city official Roberta Mattioli, presiding over the legal ceremony, graciously overlooked.

Heartfelt Vows and Cherished Traditions

The ceremony was deeply personal, with Paulina's sons and stepson playing "The Moldau" by Smetana on violin and guitar as the wedding party processed. Jeff's sister Jill and Paulina's brother Kym officiated, crafting beautiful and meaningful vows for the couple. Their words resonated deeply, emphasizing the profound sense of safety Paulina found in her family's presence. Following tradition, Jeff stomped on a glass, and the newlyweds shared multiple kisses before recessing to The Raspberries' "Go All the Way." A large group photo on a cobblestone street, rather than traditional individual portraits, captured the collective joy of their guests.

An Exquisite Reception and Unexpected Revelry

The celebration continued at Villa Crespi with a lavish dinner prepared by the hotel's nine-Michelin-starred chef, Antonino Cannavacciuolo, delighting guests with an unforgettable culinary experience. Each table was uniquely named after renowned Italian directors, with a special tribute to Czech director Miloš Forman. Paulina and Jeff shared their first dance to "Moon River," a song holding special significance for them. Amidst heartfelt speeches, an impromptu Jewish hora dance to Queen's "Don't Stop Me Now" added to the joyous atmosphere. A humorous Czech tradition unfolded when Jeff's new stepson playfully informed him that Paulina was "held hostage" at a nearby bar, leading to Jeff paying a "ransom" to a group of Argentinian football fans.

A Sweet Ending and a New Beginning

The reception concluded with the cutting of a towering wedding cake, adorned with figurines from Jeff's parents' wedding 63 years prior. Paulina playfully shared cake with Jeff, leading to a rare moment of silence from the usually talkative groom. Their wedding night brought another Czech tradition: all the furniture in their hotel room was piled onto the bed, a symbolic gesture intended to teach the newlyweds cooperation from the very beginning of their married life. Reflecting on their perfect day, Paulina and Jeff expressed immense satisfaction, cherishing the feeling of having the wedding and partner they had always dreamed of.