The Story Of Oprahs Boob On My Shoulder

You can't tell by this picture but she's floating.

Yes, it’s true.

Oprah Winfrey once rested her left boob on my right shoulder.  Her arm gently lay across my back with her left hand securely squeezing my shoulder.

This miraculous occurance happened for several reasons:

1. I had not yet had children and flying to Chicago for an extended weekend was a no-brainer.

2. My sister-in-law knew someone who knew someone who knew someone who knew someone who could get us coveted tickets to ‘The Oprah Show.’

3. And lastly, I wore the right outfit.


Let me be very clear.  I am a huge Oprah fan.  Do not even try and tell me she’s not awesome.  I’ve seen the woman in person and she looked like she was carried through the television studio by a team of four thousand fairies.  Sure, she has faults.  Well only one.  But he was AMAZING in Saturday Night Fever.  We can never forget that.

Prior to the show, I purchased an exorbitantly overpriced button down coral shirt because, really, what is the point of going to the show if you can’t spot yourself in the audience afterwards?  (This of course was suggested to me by our own Samantha Bee of The Daily Show.).  The shirt, known from this point forward as “The Shirt That Got Me On Oprah” was a fortuitous purchase.  Because essentially this is how our trip to the studio unfolded:

  • My gang and I are herded into a holding room with hundreds of other women.  Oprah topic is still a “secret.” Hoping it’s not a cooking show.
  • Find out it’s “Cooking With Rosie.” Immediately disappointed as it’s a cooking segment.  Slowly get over it when given free cookbook.
  • My group is approached by producers to see if we would like to sit in the front row.  Yes, indeed we would!  I whisper a quiet thank you to “The Shirt That Got Me On Oprah.”
  • We sit in front row next to area where Oprah will make high-five entrance.  Group feeling excited for potential opportunity to touch Oprah.
  • Another producer approaches our Group inquiring whether or not any of us enjoy “Chicken or Shrimp”.  She’s staring right at my shirt.  I let it work it’s power.
  • Suddenly getting “touch up” makeup and hair spritz to sit ON STAGE with another panicked woman.  Wait.  What the hell is happening?!
  • Start fantasizing that Oprah asks me about myself and suggests she “hook me up” with her friend Steven Spielberg.
  • Immediately imagine having a home with a pool in L.A.
  • Oprah makes Grand Entrance.  There is a globe of light around her.  Women go nuts.  I see my best friend make contact on a high-five.  My right armpit begins sweating profusely.
  • Oprah starts cooking segment with Rosie.  I am honestly 4 feet from her.  Right armpit saturated.  Honestly, why the hell don’t I sweat out of my left armpit?
  • Oprah turns in our direction. I start shoving chicken in my mouth.  It tastes like a children’s toy.  I don’t care.  I want to impress her with my test tasting skills.
  • Oh Good Lord!  She’s a foot away from me and she’s stretching her left arm.  Is she..?  Could she be…?
  • She smashes her left mammory into my face as I continue to cram chicken and shrimp-like rubber food items into my mouth.  And then I yell:


Director announces we are back from commercial.  Hold on.  That was a commercial break?  She was just coming to chit chat?  Are you saying that I could have used that moment to embrace her tightly and spew my resume credentials in her general direction?!

Oprah walks back to centre stage but if I close my eyes I can still ghost feel her boob on my shoulder.  The producer walks me to the front of the audience for a VIP seat.   The show is ending.  I sat next to my personal hero and the only thing I said to her was “I love the chicken.”  Which was a lie.  Just in case you didn’t know, anything eaten on television is made of car parts.

Oprah begins to wrap up the show but just before she does, she looks in my direction and says, and I kid you not…

“I really like your shirt.”

Well, Oprah, I really like you.  And one day, we will be friends.

I just have to figure out what to wear.


Check out previous posts by Allana:

How To Be Mom Enough

A Mother/Daughter Moment


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Article Posted 4 years Ago
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