Second Date Update Classics: The Boy Who Cried Tree + Deck The Mall

from Brooke and Jeffrey: Second Date Update · host iHeartPodcasts

Part 1 After we totally botched a Second Date for a guy a few months ago, he’s back and at this point we’re not sure if he’s trolling us or just likes the punishment. We can't let him down this time! Part 2 Imagine if you went on a date with a coworker and after the hang out, MULTIPLE PEOPLE are now avoiding you. It happened to one of our listeners and you can hear why in a Second Date!See omnystudio.com/listener for privacy information.

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This episode was published on December 20, 2025.

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