New York, NY
I was working out on a speed bag at the Reebok Sports Club when a pretty woman approached me and asked me where she could get a pair of boxing gloves. I told her she had to bring her own, but she was cute so I told her she could use mine. She took me up on the offer. She told me her name was Deb.
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I noticed she didn’t know how to hit the bag, so I showed her. After a few minutes she gave me back my gloves and thanked me. As she walked away I put them on and said, “Hey, they’re moist!” She turned around and flashed a smile. That’s when I realized it was Debbie Gibson. I confirmed later with the girl who gave out locker room keys that she was indeed in the gym that day.
Fast foward a couple of months and Gibson was appearing on “The Regis and Kathie Lee Show.” I worked in the building in the news department and one of our reporters was going to interview her for a story, so I went down with him to greet her. I introduced myself and reminded her who I was. She turned to someone in her entourage and said, “Hey, I used this guy’s boxing gloves!”
We all took the elevator up to the spot where the reporter was going to interview her. I got off at a lower floor, and trying to be smooth I backed out of the elevator and said, “Good to see you again Deb.” But as I said it I backed into a potted plant and nearly tripped. Real smooth!
Afterwards I saw the reporter and jokingly said, “I think she liked me.” And he said, “Oh yeah, you were all she talked about!”
— Sighting by MB