My Date with a Podcaster

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On a recent trip home, my family got together at my grandparents’ house. One particularly kooky aunt of mine (come to think of it, they’re all pretty kooky) asked me if I was single. I’ve been asked this question hundreds of times at family affairs, but her response was a first:

“That’s great!”

She said. “Do I have a proposition for you!”

My aunt proceeded to explain to me that she loves a certain podcast and has been listening to it since the ’70s. (And no, readers, I will not share with you the name of the podcast…) Recently, a new podcaster joined the list of shows on the roster and she adored him. He was funny and told about the woes of being a single guy in Chicago. After hearing these stories, my aunt decided to do some research – what was his last name? Was he cute? What was his email address?

This is where I come in…”Yes, Aunt Sherry, I’m single.” After hearing her story and having previously vowed to never turn down a crazy situation (which almost always leads to a crazy story for the blog), I agreed to let her send the podcaster my email address and short bio, then send it off to the podcaster in hopes that he’d respond and henceforth take me on a date so we’d fall in love, her then being credited with me finally getting married. Okay, she probably didn’t think that far in advance, but here’s what she wrote:


[Please don’t read this email on the podcast and please don’t think I’m nuts.]

I am a happy charter subscriber and faithful listener to both the [blank] Show and the [blank] podcast (I’ve been listening to [your co-host] since the 1970s).  You are hilarious on both.  It seems like [your co-host] is letting you talk more; it makes the show funnier. Both shows brighten my days.

What I’ve gleaned over the years is that you are a really good, kind-hearted person. I truly wish the best for you. You’ve mentioned in the last few months that you are looking to meet fun and attractive women. My niece, Ashley, is not in a relationship, is 30 years old, has not been married, and has no children. She lives in Logan Square and works in Chicago. She’s beautiful, outgoing, fun-loving, friendly, and genuine. Ashley is a former elementary school teacher who has a master’s degree, loves living in Chicago, and enjoys travel. Her photo is attached.

On the podcast recently you made fun of the woman who, at the Cubs game, tried to set you up with her daughter. This email is not in response to that. I’ve had this idea for months and finally asked Ashley if emailing you is OK. She said it is and would be happy to meet you. If you would like, you can contact her at [email]




My favorite parts include:

1. The first line! Haha!!

2. My email address is wrong.

The podcaster did respond to my aunt who then forwarded me the emails where I saw the incorrect email address. I decided to take fate into my own hands and email Mr. Podcaster myself. What have I to lose? An evening with a good story in the end??

The Podcaster emailed me back and asked me to get drinks. We’re going…tonight…report to come!

 A few hours later…

 So here you have it, my date with a podcaster. The date itself was very nice, but we didn’t have very much in common. He was nice and had a good sense of humor, but we didn’t have much else to talk about besides the pleasantries of a first date. I wish there were some grand climax to this story, but really the highlight came in that awesome email that my aunt sent. Sorry, Aunt Sherry, there won’t be a love connection on this one, but thanks for trying!!

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Contributor - Newcomer, Yogi, Road-tripper, World Traveler, Overachiever, Goodie Two-Shoes, Bookworm, Salsera, Writer

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