The Tamesis
Singer Madison McFerrin and celebrity trainer Jesse Cunningham are one of the lucky few to experience a whirlwind romance. The two met in 2024 at DJ Jazzy Jeff’s Playlist Retreat, a multi-day event for artists to create music and collaborate. “I overheard Madison’s music during our first nightly studio session and found myself completely smitten,” Jesse recalls. “The next day I worked up the courage to stop her on her way to the bathroom and told her I loved her music. From then on, we spent the next three days falling in love forever.”
“All we did was laugh and play and keep talking about how we felt like little kids around each other,” Madison added.
After the retreat, Madison visited Jesse, who was living in Washington, D.C. at the time, and by the end of the trip, they decided that he should move to Los Angeles to be with her. “Within days, I knew I had found my person, that I had found it forever,” Jesse shared. They will return to Playlist Retreat as newlyweds in 2025.
The couple admitted they didn’t have a traditional engagement ceremony. “We talked about getting married within a few months of meeting — it felt like it was inevitable,” Madison said. “Once we actually decided on a date and started planning, we contacted my dear family friend (and future officiant) Frank Everett, vice chairman of Sotheby’s Jewelry, to help us find a ring designer. Given the style I wanted, he suggested Maggi Simpkins—it turns out she and Jacy had met ten years ago!” The process of designing the ring took five weeks in the summer of 2025. On the day the mail arrived, Madison waited for Jesse so they could see it together for the first time. “Before I even opened it, we were both in tears realizing the moment that was coming,” Jesse said. “I was holding back tears and opened the box and asked her, ‘Madison, will you marry me?'” After she said “yes,” the couple “hugged all day long,” Jesse recalled.
Madison and Jesse planned their entire wedding in just three months and worked with Gabriela Pilar Events to help make the celebration a reality. “This beautiful wedding would not have been possible without Gabriella’s guidance! She made everything seamless and hands-on,” said the bride. “It turns out that when you don’t have time for indecision, things can actually go pretty smoothly.” The couple will exchange vows on September 13, 2025, at the late comedian John Witherspoon’s home in Sherman Oaks, California. “His widow, Angela Robinson, and my mom have been close friends since before I was born,” Madison explains. “Their home has always been as vibrant and magical as Angela’s art collection – the ivy-wrapped exterior, rooms filled with color and creativity provided the perfect backdrop for our garden wedding.” The venue also provided inspiration for their wedding party outfits. “We wanted to feel like we were all flowers in Angela’s beautiful garden,” Madison said. So the couple gave them a color palette to follow and asked them to follow a “tasteful garden-chic vibe.”
