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The Pen Pals Podcast

Dec 28, 2022

Dear Pennies & Pallers,

In letter one, K wants advice for how to start dating in her 30s, as someone who has never had a real kiss. Letter two is from Meagan who asks about our favorite childhood smells.

We also talk treading water, Illinois geography, touching objects with your tongue, and more!

We wish you well,...


Dec 21, 2022

Dear Pennies & Pallers,

This week we are joined by our friend Todd Glass! Letter one comes Gemma, whose colleague lacks emotional boundaries at work. In our second letter, Danny wants advice on getting acceptance from their parents. We also talk roommates, Quantum Leap, Rory’s literacy, and more!

We wish you well,...


Dec 14, 2022

Dear Pennies & Pallers,

Our first letter comes from Kevin, who wants his partner to tell him he’s pretty. Letter two is from Clay, who is getting dressed up for a wedding and wants input.

We also talk “inside baseball”, Joan Allen, slang, and more!

We wish you well, sincerely,

Your Pen Pals Daniel Van Kirk and...


Dec 7, 2022

Dear Pennies & Pallers,

This week we are coming to you live from the Come & Take It Comedy Festival, and are joined by our friends Jackie Kashian and Sean Patton! In letter one, Austin writes in about his hatred of streaming services. Letter two comes from Rob, who asks for our definitive Disney Song rankings.

We also...


Nov 30, 2022

Dear Pennies & Pallers,

This week we are joined by our friend Dierdre Friel! Letter one comes from a teacher whose colleague lacks emotional boundaries at work. In our second letter, Paul wants to know how we feel about our names. We also talk holiday food, Twitter, Willie Wonka, and more!

We wish you well,...