From friendship to happily ever after

Aug 10

3 min read

Taylor Leatherwood and Rob Pillow wed in a spirited NOLA celebration

I first met Rob at Ole Miss, where our relationship began in a completely platonic way. After graduation, life took us in different directions, and we each had time to grow and figure things out on our own. Over the next 10 years, we ventured through life, experiencing new challenges and milestones apart from each other.

A ROMANTIC RECONNECTION

Then, during Rob’s trip to Paris for the Olympics, his curiosity was piqued when my name came up in conversation. He decided to reach out, eager to see how I was doing after all those years. What started as a simple message turned into meaningful conversations that felt both nostalgic and refreshing.

As the months went by, we began flying back and forth to see each other, sharing our lives and having honest discussions. It was during this time that I realized our connection had deepened into something more. I found myself falling in love with him, recognizing that our friendship had transformed into a beautiful relationship.

THE PROPOSAL

Rob’s proposal was a moment I’ll always cherish. He flew from Washington, D.C. to Arizona without me knowing, and my local friends were in on the surprise. At the Wrigley Mansion in Phoenix, he expressed his feelings and asked me to spend my life with him. At that moment, I knew this was just the beginning of our journey together. Soon after, I moved back to Mississippi, excited to start this new chapter side by side with him.

THE BIG DAY

Our wedding weekend was truly a New Orleans celebration from start to finish. We stayed at the Roosevelt Hotel and kicked things off on Friday with a bridal lunch at Brennan’s restaurant and a rehearsal, followed by a rehearsal dinner at the Southern Yacht Club and a welcome party at the Double Dealer beneath the Orpheum.

Saturday, May 23, was the big day. Rob and I shared a first look, followed by our private vows and communion. We chose to do those moments privately so we could be fully present with each other before the whirlwind of the celebration.

Our ceremony was an Episcopalian service led by a friend, the Rev. William Boyles, held inside the Orpheum Theater. Immediately following, we had a celebratory second line through the rainy streets. When we returned, guests enjoyed a cocktail hour while Rob and I shared a quick, private meal together.

Then came our grand entrance, first dances, and from that point on, we never left the dance floor. At one point, we cut the cake and toasted with espresso martinis, one of our favorite moments, before diving right back into the celebration.

We also made intentional choices about what mattered to us, skipping certain traditions like the bouquet and garter toss and focusing instead on the parts of the night that felt authentic. Our wedding party was big — 18 bridesmaids and groomsmen, all close friends from different chapters of our lives — which made the day feel even more personal.

We really wanted the entire experience to feel fun, immersive and meaningful, so we leaned fully into the spirit of the city. Our bridesmaids wore purple, and our florals were green and white. We had gold accents throughout. The food was classic Cajun cuisine; fried alligator and gumbo were crowd favorites, and the whole atmosphere felt like a joyful nod to Mardi Gras. It was everything we hoped for: lively, meaningful and unforgettable for us and everyone who came to celebrate.