The Day I Missed My Chance to Meet Oprah

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Updated: Aug. 3, 2016

Originally Published: July 14, 2015

Back in 2007, my husband and I found ourselves at a conference in Chicago. While he immersed himself in sessions, I was off gallivanting down the Miracle Mile, soaking up the sights and indulging in a bit of mischief until his educational endeavors wrapped up. But, more importantly, I was on a quest to find Oprah.

Once upon a time, I was Oprah’s number one fan—no question about it. I never missed an episode, made a daily effort to “Remember My Spirit,” and often kicked off conversations with, “I saw on Oprah the other day…” My afternoons were sacred: tea was brewed, laundry was folded, and wisdom was absorbed. The Oprah Winfrey Show was my sanctuary.

So, when I discovered that we would be in Chicago, I wasted no time trying to snag tickets to a taping. I contacted everyone and everything—emails, sign-up forms, waiting lists, even jokingly offering my firstborn to Stedman! Yet, nothing came of my efforts. Still, I boarded the plane with hope, convinced that fate would allow me to meet the queen of talk shows and become her best friend.

Staying at a downtown hotel, I made it a point to chat up the concierge for any insider tips on how to score a ticket. I did everything short of sliding him a crisp $100 bill and my room key (which would have been pretty awkward with my husband in tow) to persuade him to help me. All he could manage was to add my name to a list he maintained for complimentary tickets—something he claimed happened occasionally. For three days, I diligently added my name to The List.

But on the fourth day, after a long morning wandering the city, I returned to the hotel only to realize I was too late to add my name. My heart sank.

Despite the oversight, I clung to the belief that my connection with Oprah transcended a simple list. After all, I had declared my desire to meet her to the universe! I had her latest Book Club pick in my bag, which I had been reading at a local Starbucks. I deserved this encounter, right?

The next morning, as my husband and I stepped into the elevator, we were joined by two overwhelmingly cheerful women in their forties. They were practically bouncing with excitement, which led me to assume they were just fellow moms reveling in a kid-free getaway.

Chipper Woman No. 1 exclaimed, “I can’t BELIEVE our hotel was chosen to see Oprah!!!”

Chipper Woman No. 2 chimed in, “I KNOW! Putting our names on the list for four days totally paid off!!!”

Cue the tears. My husband was left bewildered as I had a small but dignified meltdown right there in the elevator.

It was one single day of distraction that cost me everything. While I was off enjoying the city, my bond with Oprah had been shattered.

As if the universe wanted to add insult to injury, I later bumped into the two ecstatic women after their taping. Naturally. And what did I learn? Patrick Swayze had made a surprise appearance! The show where I should have been front and center. The show where I could have seen my idol up close. I could hardly contain myself in the hotel lobby, all while imagining the missed opportunity of seeing Swayze himself.

Sigh. It could have been worse. At least it wasn’t Oprah’s Favorite Things, right? But still—PATRICK SWAYZE! Johnny from Dirty Dancing! Sam from Ghost! Dalton from Road House!

Someday, I’ll meet Oprah. And when that day comes, I promise to keep my cool, unlike those exuberant ladies in the elevator. But jumping on a couch? Well, that might just be unavoidable.

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In summary, a missed opportunity to meet Oprah led to an unexpected encounter with exuberant fans and the revelation that luck just wasn’t on my side that day. But I remain hopeful for the future!

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