Today, I have the gentle joy and heartfelt privilege of introducing Cassidy McGuinn, a warm, witty Irish-American blogger from Boston whose musings drift gracefully across topics like love, music, family, running, and baseball, with a healthy sprinkle of humor and heart. Cassidy is the woman behind Cassidy’s Quest, a blog and vlog that have quietly resonated with readers looking for hope, perspective, and a good laugh or two. Whether she’s reminiscing about Del’s frozen lemonade in Newport, cheering on the Red Sox (with some side love for the Blue Jays and Mariners), or sharing vulnerable moments from her transition, Cassidy brings the kind of authenticity that feels like a deep breath on a hard day. Cassidy came out as a transgender woman at 46, in what she describes as a moment of sleepless clarity, honesty, and fierce resolve. Since then, her journey has unfolded with courage, humor, and grace.
Her words have helped others feel seen, understood, and encouraged to walk their own paths, with petticoats, ponytails, or whatever suits them best. From her love of 1950s-inspired fashion to her reflections on self-acceptance, Cassidy radiates kindness and wisdom, often wrapped in the colors of a striped dress or the energy of a runner’s high. In this interview, Cassidy opens her heart to talk about the importance of humor in transition, the ache of family estrangement, the power of finding one’s own love within, and her dreams for a better world, one where a transgender First Lady or President isn’t a fantasy, but a real possibility. She speaks with humility, but her impact is quietly radiant. I invite you to meet Cassidy not only as a blogger or baseball fan, but as a woman who has turned self-discovery into a beautiful act of generosity.
