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My Most Embarrassing Moment

My most embarrassing moment

I began babysitting for my high school cheerleading coach, Toni, when I was about 14 years old. At that time, she had one boy, Carter, and was pregnant with Lauren. By the time I graduated high school she had three, beautiful children whom I loved and cared for as if they were my own little brothers and sister.

Right before I went away for college, Toni asked me to go on vacation with her family and her brother’s family of four to help with the kids. I said yes, and we had a great time. However, on the very last night of our trip, something went terribly wrong…

I woke up that last morning to someone nudging my shoulder and saying my name. It was the mother of the second family, the family I had just met that week.

“Hey Ashley, good morning,” she said kindly. “I just want to thank you for everything you did this week and let you know that we really enjoyed getting to know you. We are leaving now, before you, so I wanted to say goodbye.”

I rubbed my eyes, feeling incredibly disoriented, I looked around the room and noticed something peculiar… “Why am I in here?” I asked.

“Oh… yes… well… last night you came into our room in the middle of the night and you used the bathroom … and then you got in bed with all of us … we tried to wake you, but you were sound asleep … so we just ended up leaving you,” she said cautiously.

I died. Well actually, I slept-walked, apparently … but in that very moment all that I wanted to do was curl up in a ball and go back to sleep—I wanted to pretend it was all a dream. But it wasn’t.

Later that day, Toni called me to see how I was doing. She couldn’t stop laughing about the whole situation. She told me that when she woke up early that morning, she went into “my room” to tell me that they had packed the car and were going to get an early start on the road back to Indiana… But she was shocked when she found my bed ruffled, but empty.

She panicked a little bit as she called my phone and searched around the condo, but couldn’t find me. After about 10 minutes of searching, she went into her brother’s family’s room to tell them I was missing … but I wasn’t. I was found. Right there in bed with her brother, sister-in-law, niece and nephew … tucked comfortably under the comforter, snoozing away.

Toni told me that she would burst out laughing every so often on their drive home whenever she recalled the sight. (She also took a couple pictures.) It took a long time for me to be able to laugh about it, because I was so mortified. Now it’s one of my all-time favorite stories to tell. Needless to say, I always win the “most embarrassing moment” game with this ace of a memory.


Still laughing? Don’t miss 9 Awkward Moments in a Woman’s Life, 10 Funny Things All Women Do, and Grocery Shopping with Small Children.
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Don’t be fooled by Ashley’s quiet presence. She’s an internal processor who just might overthink from time to time. When she’s not caught up in her thoughts, she’s usually writing them or enjoying the thoughts of others. She’s a wife, new mom, and lover of all things pretty.

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