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Roberto is a Captain

July 31, 2025 · 30 min

Show notes

This week, we’re joined by Roberto Portales—a Cuban-American platoon leader, former football player, and proud Chatty Cathy (after two drinks).

Roberto opens up about growing up in a loud, loving Tampa household, serving in Afghanistan, and coming out later in life—after years of living in hyper-masculine spaces.

We talk about West Point hazing, war zone drinking rules, and why masculinity doesn’t equal heterosexuality.

Also: fake Instagram accounts, dating in your twenties, Cuban family chaos, and yes… peeing in bed.

All episodes of Tyler and Gabriel

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