Trust Issues and Breakthroughs: How Gabby Windey and Robby Hoffman Built Their Marriage

When Gabby Windey and Robby Hoffman first started dating, things moved fast—maybe too fast for Windey’s comfort. But what could’ve become a relationship-ending friction instead became the foundation for something genuine, according to Hoffman’s candid appearance on the“Call Her Daddy”podcast on Wednesday, May 20.

The early tension wasn’t about incompatibility. It was about trust. Windey, 35, brought emotional baggage from her past into the relationship, struggling to believe in Hoffman’s commitment even as she felt drawn to it. Hoffman, 36, recognized that this wasn’t about her personally—it was about patterns Windey had learned as a child. When she spoke up about problems back then, they became weaponized against her, so she’d internalized the lesson that voicing concerns meant risking abandonment. That kind of wound doesn’t heal overnight, and Hoffman understood that.

What makes their story remarkable is how they navigated it. Rather than pushing Windey to“just trust”him, they let commitment itself become the evidence. With each step—moving in together, getting married—Windey experienced safety in a way her past hadn’t allowed. Each milestone didn’t just deepen their bond; it rewired her nervous system’s response to vulnerability. As Hoffman explained on the podcast, every time Windey appeared to pull back, she’d actually come around feeling ten times closer once the commitment solidified.

The couple, who went public with their relationship in August 2023 (a year after Windey’s season 19 co-Bachelorette run), surprised fans in early 2025 by revealing they’d gotten married. That journey from doubt to“I really trust that you love me”—Windey’s words at the altar—represents something deeper than a Hollywood love story. It’s a master class in what happens when two people decide that healing together matters more than moving fast.

Hoffman also noted that neither partner saw themselves as responsible for fixing the other. Instead, they’re healing alongside each other, which is an entirely different—and healthier—dynamic. When Windey came out as queer publicly, the Bachelor Nation fandom embraced them both, a welcome surprise that likely eased what could’ve been an anxious moment.