Questions & Quitting with Kirkland

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Siobhan and Kirkland sit down for their first real catch-up since December 2022, trading updates on life, loss, and the strange ways the world has shifted. Kirkland shares how catching COVID pushed him to finally quit drinking, the financial reality of walking away from the bar life, and the highlights of his 11-year trivia-hosting streak—complete with surprise winners, candy slogans, and a generous benefactor who changed the game.

The conversation goes deep on chronic pain—his sickle cell and hip surgeries, Siobhan’s endometriosis—and the ways it shapes travel, relationships, and everyday choices. They wander through stories of grief that shows up out of nowhere, travel magnets that hold whole memories, and what it means to quit the things that drain you while holding onto what brings joy.

It’s a mix of laughter, truth bombs, and hard-earned wisdom—served with the same unfiltered honesty you’ve come to expect from Ducking Realitea.