What’s It Really Like To Win A Date With A Celebrity Contest? 

24. I had a Meet and greet with Kenny Chesney when no shirt no shoes no problem album came out. He was shorter than I expected. He was very nice to everyone but I never got a chance to introduce myself or get a picture or anything. I won a contest along with fifteen or twenty others, they were mostly women, and the lady with Kenny organizing the introductions and I’m guessing she ran the meet and greet in general pulled me out of line with no context and left me hanging there. I was 14 and didn’t know what to do so I waited and after everyone else got through the line we were shown out of the room. It broke my heart because i just wanted an opportunity to tell him he recorded my favorite song ever. It’s still my favorite to this day. I really regret not standing up for myself.

25. I once won an opportunity to meet Jamie Oliver and have a catered lunch with the other winners (there were other winners too) and some additional special guests who had also been invited. There was a lot of food and the whole thing went for about 3 to 4 hours. I had almost zero expectations, so it was pretty good. They were generous with the food and time, and Jamie made sure he went around and talked to all of us. I got a personally signed book as well, which I wasn’t expecting and was done towards the end as it was wrapping up.

He’s a very nice person, exactly like he is on TV. Very open to having people walk up to him and chat. Not at all pretentious or dismissive, like some other celebrities who I’ve heard put on a fake-friendly public persona.

Reading some of the comments I’ve seen posted about him make me a bit sad, I’m sure some people just don’t like his personality or style for whatever reason, but from my experience meeting him in-person he really is a pretty cool and friendly guy.