31 Regular People Share Memorable Celebrity Encounters

7.

“Many years ago, while working as a waiter at a high-end restaurant in Wellesley, MA, I was made responsible for managing a 3:00 p.m. lunch reservation for a party of two under the name Willingham. Sure enough, at 3:00 p.m., Willingham, a very large, muscular male, entered the restaurant. I politely told him I needed a few minutes to get him seated while I tended to some other dining matters. I turned and headed towards the back of the restaurant and the kitchen. As I did, I watched Willingham exit the restaurant. Moments later, Willingham re-entered the restaurant through the same front door and escorted Oprah Winfrey and a young female guest into the bistro. My jaw dropped and almost hit the floor.”

“I stood in awe, mouth agape, and watched Willingham as he walked beside Oprah and her young guest. He found them a nice, quiet, isolated table in a small area of the restaurant and sat them. He then turned, locked eyes with me, and beckoned me to his side. He said to me, ‘I’m gonna be sitting right here,’ and pointed to a separate table maybe 10 feet away. ‘You bring me the check when you’re done.’ When he sat, his baggy, oversized shirt pulled up a bit, revealing a concealed, holstered pistol on his hip. Willingham, I realized, was the bodyguard. 

I approached Oprah’s table, all the while remembering Willingham was watching everything. And he had a gun. ‘Hello and welcome,’ I muttered with hesitation. ‘My name’s Tommy I’ll be taking care of you today.’ Oprah smiled up at me, almost saintly, removed her glasses, and said, ‘Well Tommy, this is my first time here. Can you please walk me through your menu and perhaps make some recommendations?’ Again, my jaw dropped. This time it hit the floor. So, with as much grace as I could manage, I walked Oprah through the menu, after which she decided on a cup of chicken tortilla soup and a hot tea. She was the nicest, most polite, and most respectful guest I have ever served, regardless of her celebrity status.

Oprah spent about an hour at the restaurant having lunch with her friend. Upon her exit, she stopped to say hello to everyone she passed. I brought Willingham the check as requested. He paid, then escorted Oprah out to a waiting chauffeur.
Once they departed, I scanned the credit card receipt that Willingham had paid with. Willingham left a 100% tip.”

—Anonymous