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What happens when a radio host's schedule includes both a prison comedy show and officiating his daughter's wedding in the same month? Chris Bennett's wildly varied May calendar becomes the perfect launchpad for this laugh-filled episode that dives into unconventional performances, awkward dating stories, and heartwarming family news.

Producer Ryan kicks things off by catching up with Chris about his upcoming shows—from a homeowners association event in Mesa to two separate comedy performances at a Yuma prison. The prison gig has Chris contemplating whether to channel Johnny Cash by wearing all-black attire and planning to film the shows for a potential comedy special called "Chris Goes to Prison." Between jokes about inmates not getting his references, Chris reveals he'll also be officiating his daughter's wedding later this month.

The episode takes an unexpected turn when Ryan shares an exclusive dating story saved for podcast listeners only. After finally matching with someone attractive on a dating app, Ryan discovered she was in an open marriage that required husband pre-approval for dates. The resulting three-person meetup at a local brewery started promisingly but ended with Ryan being ghosted after the husband informed him there "wasn't a vibe." As one Facebook Live viewer commented, Ryan may have narrowly escaped being trafficked, though he quipped traffickers probably weren't targeting "46-year-old single men with chihuahua dogs."

Between games celebrating Noise Awareness Day and National Bugs Bunny trivia, the most heartwarming moment comes when Janine Ford shares her emotional Easter weekend discovery—both her sons and their partners are expecting babies due the same week in December. The surprise dual pregnancy announcements, including one revealed through a scratch-off card, created an unforgettable family celebration.

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