Neither of us was looking for love when we met performing at a basement comedy show. I’m a widower raising four children, and she is a devoted single mother. A charming and fun encounter between two artists; both of us focused on growing ourselves. Between chance meetings at open mics, a "not-a-date" that turned out to be one, and countless shared laughs, the stars seemed determined to bring us together. Ever since, we've been collecting "firsts"…falling more deeply in love with every adventure.

One of our favorite memories is what turned out to be our first date… though neither of us realized it at the time. We met for dinner, awkwardly shook hands like we were at a business meeting, then saw a great variety show at a beautiful old theater. Afterward, in the light rain, I walked Rachel to her car. When we finally went in for a shy goodbye hug, her comically oversized umbrella crashed into my forehead. The awkwardness disappeared, and we’ve been laughing together ever since.

$20,000 sounds like a great way to continue deepening the connections within our newly blended family. We’d explore fun and unique places, immerse ourselves in art, try foods we’ve never tasted before, and embrace new experiences together. The value wouldn’t be in purchased items, rather in our gained perspectives, the conversations we share, and the memories we create—experiences that help turn separate lives into a family.