Singer Madison McFerrin and celebrity trainer Jacy Cunningham are among the few lucky people to experience a whirlwind romance. The two met at DJ Jazzy Jeff’s Playlist Retreat in 2024, a multi-day event for artists to work on music and collaborate. “During the first evening studio session, I overheard Madison’s music and found myself smitten to the core,” remembers Jacy. “The next day, I mustered up the courage to stop her on her way to the bathroom and share that I loved her music. From that point forward, we spent the next three days falling into a timeless love.”
“All we did was laugh and play, constantly remarking how we felt like little kids around one another,” Madison adds.
After the retreat, Madison visited Jacy in Washington, D.C., where he lived at the time, and by the end of the trip, they decided he would move to Los Angeles to be with her. “Within a few days, I knew that I had found my person, that I had found forever,” shares Jacy. They would return to the Playlist Retreat in 2025 as newlyweds.
The couple admits they didn’t have a traditional engagement. “We talked about getting married within months of knowing each other—it simply felt inevitable,” says Madison. “Once we actually decided we wanted to pick a date and start planning, we hit up my dear family friend (and would-be officiant), vice chairman of Sotheby’s Jewelry, Frank Everett, to help us source a ring designer. Given the style I was going for, he suggested Maggi Simpkins—turns out she and Jacy had known each other a decade prior!” The process of designing the ring took five weeks during the summer of 2025. On the day it arrived in the mail, Madison waited for Jacy so they could see it for the first time together. “Before I could finish opening it, we were both in tears recognizing the impending moment,” says Jacy. “I opened the box, holding back a wealth of tears, and asked her, ‘Madison, will you marry me?’” After she replied “yes,” the couple “hugged for what felt like an entire day,” Jacy recalls.
Madison and Jacy planned their entire wedding in just a three-month window, working with Gabriela Pilar Events to help the celebration come to life. “Without Gabriela’s guidance, this beautiful wedding would not have been possible! She made everything seamless and was super hands on,” says the bride. “It turns out that when you don’t have time to be indecisive, things can actually run pretty smoothly.” The couple would exchange vows on September 13, 2025, at the home of the late comedian John Witherspoon in Sherman Oaks, California. “His widow, Angela Robinson, and my mom have been dear friends since before I was born,” explains Madison. “Their home has always been as vibrant and magical as Angela’s art collection—the ivy-wrapped exterior, rooms overflowing with color and creativity provided the perfect backdrop for our garden wedding.” The venue also inspired their wedding party’s attire. “We wanted it to feel like we were all flowers in Angela’s beautiful garden,” says Madison. So, the couple gave them a color palette to follow and asked them to follow an “elevated garden chic vibe.”
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