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The Pen Pals Podcast

Oct 27, 2021

Dear Pennies & Pallers,

First, we have a hot-off-the-presses (night of!) letter from a Pen Pal who was witness to a deeply unpleasant view when her beloved former boss sat down in short shorts. She wants to know: have we ever caught an unintentional glimpse of someone’s body that made us cringe?

In our second letter,...


Oct 20, 2021

Dear Pennies & Pallers,

This week we are joined by the hilarious Andy Samberg!


In our first letter, the best summer camp employee ever asks us about our preferred toilet paper orientation (over or under?).
In our second letter, a Pen Pal learns that they are the great-great-grandson of a horse thief. Rory asks: is...


Oct 13, 2021

Dear Pennies & Pallers,

This week we are joined by our friend (and your new Pen Pal), the hilarious Kyle Kinane!

In the first letter, our Pen Pal explains that her home is haunted by the ghost of her husband’s father. She wants to know: how can you go #F2F (face-to-face) with a spirit? 

In this week’s second...


Oct 6, 2021

Dear Pennies & Pallers,

This week we are joined by our friend Matt Walsh (Veep star! UCB co-founder! Chicago Bears superfan!).

In our first letter, a Pen Pal describes losing a cousin that felt like a “cosmic twin”. We discuss the power in feeling truly connected with another person - be it a relative, friend,...