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Derek Czaplewski

Administrative Assistant

Born and raised in Omaha, Nebraska, Derek has called Chicago home for the past two decades. Derek has previously worked as an actor, as an arts administrator and as an administrative assistant. (He prefers jobs that start with the letter 'A'.)

In his free time, Derek enjoys writing, thrifting, hiking and watching television. Derek resides in the Irving Park Neighborhood of Chicago with his husband, Josh, and their dog, Leo.

Anything you do, let it come from you. Then it will be new. Give us more to see...

Stephen Sondheim, Sunday in the Park with George

Favorite Vacation Spot

Somewhere nature-adjacent but with a pool & hot tub

Favorite Beverage


Favorite TV Show

Tie between 30 Rock & The Muppet Show

Favorite Challenge Food

Fruity Pebbles Cereal

Hidden Talent

Nostril flaring

Weird Fact


Fun Fact

Hiked roughly 427 miles of the Appalachian Trail over 7 weeks in 2018

Something You Hate

Ironing clothes

Favorite Pastime

Watching horror movies

Favorite Restaurant

Angelo's Wine Bar

Favorite Song To Dance To

Don't Stop Me Now by Queen

First Concert

Weird Al Yankovic & The Monkees

Favorite Nicholas Cage Movie

Raising Arizona

Most Famous Celebrity Met

Robin Williams

First Job

Popcorn Store Employee

What You Wanted to Be When You Grew Up