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Jenny Riddle

I Asked a Roomful of Teenagers One Question

April 13, 2026 Jenny Riddle Leave a Comment

A few weeks ago, I walked back into York High School to teach a storytelling workshop during Fine Arts Week.

Walking into that building always carries a lot of history for me.

As a senior, I was on stage as Dolly in Hello, Dolly!

My dad taught English there for many years and became something of a legend among his students for having them memorize poetry while standing on their chairs. (Popping into his classroom to borrow the car keys to take my friends to McDonald's during my 4th … [Read more...] about I Asked a Roomful of Teenagers One Question

Filed Under: Blog

Bearing Witness

February 11, 2026 Jenny Riddle Leave a Comment

As we paid tribute to Dr. Martin Luther King last month, I found myself, again, thinking about the impact of words on our lives.

Recently, I came across a fascinating article about Patrick Henry in The Atlantic, part of a broader focus on this year’s 250th anniversary of the American Revolution.

Patrick Henry is remembered as the most powerful speaker of that era, hands down, by his fellow founders, including Benjamin Franklin and Thomas Jefferson. John Adams declared Henry, “the … [Read more...] about Bearing Witness

Filed Under: Uncategorized

Not Just Handshakes—Something More

January 4, 2026 Jenny Riddle Leave a Comment

Sixteen people gather around our dining room table on Christmas Eve. Some know each other well. Many don’t.

So here’s the question I’m noodling for days beforehand: How do I get that many people—across ages, families, and familiarity—truly connected?

I finally land on something I call Christmas Eve Table Talk. On each plate rests a 5x7 handcrafted card inviting each person to choose one thing to share: a story, a poem, or a song.

As people notice the Table Talk cards, I sense a little … [Read more...] about Not Just Handshakes—Something More

Filed Under: Blog

Why You Should Sing With Strangers

November 18, 2025 Jenny Riddle Leave a Comment

A few weeks ago, on a Monday night, my husband, son, sister, and I were settled into our seats at the first Northwestern basketball game of the season.

Like at all sporting events, the whole stadium was invited to stand and listen to the National Anthem before tipoff.

I say invited to listen because I’ve realized, with growing frustration, that people no longer sing the National Anthem together. It has become a performance. A soloist steps up to showcase their vocal acrobatics while the … [Read more...] about Why You Should Sing With Strangers

Filed Under: Blog

6’4″, Tattooed, and Kind

September 10, 2025 Jenny Riddle Leave a Comment

It’s Tuesday night, and I’ve just walked into the indoor pickleball courts at Lifetime in Oak Brook. I’ll be honest: I wasn’t quite sure what I was getting into. Would I be able to hold my own? And what would the people be like?

Having played tennis for most of my life, I know that world and can easily adapt—or at least act as if I know what I’m doing. But pickleball? A whole new milieu. I wasn’t sure if I could pull it off here, but I knew one thing: I was going to die trying.

I’d been … [Read more...] about 6’4″, Tattooed, and Kind

Filed Under: Blog

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About Jenny

Jenny Riddle Bio Image

Jenny Riddle is a dynamic speaker, trainer, and communication expert who has a special way of helping people not just communicate, but truly connect .
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