Roberto is a Captain

This week, we’re joined by Roberto Portales—a platoon leader, football player, and self-proclaimed Chatty Cathy (after two drinks). Born and raised in Tampa, Roberto grew up in a loud, loving Cuban household where family drama and affection went hand-in-hand. He started playing baseball at four (coached by his dad), switched to football at 14, and wrestled to stay in shape. His world was full of discipline, tradition, and masculinity—long before he ever questioned his sexuality. Roberto takes us through his journey from West Point to Afghanistan, from dating girls in high school to realizing—later in life—that he was gay. He opens up about being surrounded by straight friends, having no gay community until he moved to Los Angeles, and how he never changed who he was… just became more himself. Even in the most masculine spaces, his identity was never about labels—it was about loyalty, love, and being real. He also shares the story of how he met his partner, Trevor, and how their relationship grew from unexpected connection to real partnership. From making sacrifices to navigating differences, Roberto opens up about what it means to show up fully in love—especially after coming out later in life. We talk about the pressure to fit into straight environments, coming out in your twenties, and why masculinity doesn’t equal heterosexuality. We also get into fake Instagram accounts, bad drinking habits, gay rights, Cuban family chaos, and the beautiful weirdness of peeing in bed (don’t ask—just listen). Also in this episode: war zone drinking rules, the worst first day at West Point, and why growing up without a cell phone might’ve been the greatest gift of all. Follow us: @tylerandgabriel @rjportales 🎙️ New episodes every week 🌈 Subscribe and join the journey