Writing Contest- If I Was Entering- My Night With Oprah

Oprah Winfrey

So folks as you know, I am having a writing contest on what you would say to Oprah in 400 words or less. If I was entering, here is my imaginary conversation with Oprah. Enjoy!!

The scene: A Courtyard by Marriott, Dayton, Ohio.

Reason: Soccer tournament. Oprah has agreed to meet with me. I’m suddenly wondering, ‘why not Lisa Ling?’

That night, we head down to the lobby where I produce my friends’ and my favorite card game: Cards Against Humanity. I look over to see Oprah putting her bottle of wine down next to my box.

“I’m sorry, Le Cigare, isn’t that like a $70 bottle of wine?” I ask.

“Who knows?” She shrugs. “I just told my sommelier to pick out a bottle for this soccer tournament and he chose this one.”

“Ok, but I’m telling you now, that shits gonna get knocked over by a stray soccer ball at some point tonight. That’s why you bring a box. Also, are you gonna drink or are you gonna drank Oprah?” I say, dramatically dropping my back with the word drank.

“I’m gooonnnnaaaaaa’ DRANK!” She says with the enthusiasm usually reserved for her tv show.

We begin Cards Against Humanity…

“You ever play?” A asks her.

“Yeah, Steadman and I played once with Barbara Walters. She walked out when we couldn’t stop laughing at the Rosie O’Donnell card paired with LickingThings To Claim Them As Your Own card.”

Three sheets to the wind, my friend N asks, “now do you call him Stedman or Studman?” She asks, clearly pleased with her joke.

Surprisingly, Oprah loved it. “Well baby, Stedman during the day…..and Studman at night,” she says, thrusting her pelvis.

We all break out in laughter.

45 minutes into the game…….

“Look under your seats LADIES! It’s a FLESHLIGHT!! You get a fleshlight!” She points to me, “and you get a fleshlight! Everyone gets a fleshlight.”

“Hey, there’s nothing under my seat,” E says disappointed.

“Did you really think Oprah would not only buy fleshlights for strangers but place them under our chairs? It’s her card. She’s re-enacting her famous car scene.

2 hours into the game……

“Then he said I went to bed with Beyonce, and woke up with Precious!” I screamed. Giggles everywhere.

“O, did you have a good time? We have to get up in 7 hours so lets hit the hay.”

“Hot Mess, anytime you want an interview, call me. If anything, gives me a chance to unwind. And you were wrong.” She says.

“‘Bout what?” I ask.

“That shit didn’t get knocked over. It’s all in my belly, including some of your boxed wine.”


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