Matt and Shane's Secret Podcast Ep 587 - PHIL (feat. Steve Gerben & Chris O'Connor)
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Nov 26, 2025 Steve Gerben, a comedian and budding expert on all things dating, shares his real-life experiences with online dating, line dancing, and the quirks of first-date etiquette. He opens up about family stories and awkward dating moments, balancing humor with relatable insights. The discussion also touches on Steve's work in theater, a knee injury, and volunteering as a coach, all woven together with lighthearted anecdotes. Listeners can expect plenty of laughs and authentic conversation about navigating love and life.
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Rural Upbringing And Tough Parenting
- Phil recalls his dad putting kittens in a box and sending them down the creek when there were too many cats around their farm.
- He uses rural parenting stories to explain tough, pragmatic choices growing up on a farm.
Pool-Cover Mishap Turned Funny Memory
- Phil describes a pool-cover mishap where a submersible pump sat on top of the tarp and funneled water into the pool.
- He narrates crawling out of the tarp and thinking it was a weird way to die, which he laughs about now.
Expect Dating Apps To Change Over Time
- When returning to dating apps, expect different results over time and adjust expectations; persistence can pay off.
- Steve notes that being known as funny now changed his dating-app success compared with six years ago.
