The Rat Pack

Many years ago, I was at Tavern on Rush in Chicago with some friends for a holiday dinner. As we were leaving, my friend spots a guy who is a celebrity. She said, you should get your picture with him, he is famous! I said, I am not sure who he is? She said, you know him, he is a comedian.

This guy can tell we are talking about him, so he comes over and introduces himself. My friend says, she wants a picture with you. He said, I will take a picture on one condition, I said, what is that? He said, only if you send it to me.

I said, well, that is easy. No problem. We take the picture, he gives me his phone number and we start chatting. Once I learn more about him, it was easy to see that he is indeed super successful. He exudes charm, charisma and humor.

So, I send him the picture and he said he will let me know next time he is in Chicago. It occurred to me shortly thereafter that this was such an unassuming way to get someone’s contact information! He now has my digits and he replied back that he wants to go to dinner.

Now, this guy is about 30 years older than me (I googled), so I assumed he was just looking for a new friend. Yes, I just fell off the turnip truck.

A couple of weeks later, he reaches out and sets up plans for dinner. This guy is very old school chivalrous (which I love). We are talking “walk on the outside of the sidewalk, pull out the chair, stand when you stand”, type of old school chivalry.

He has the nicest table reserved for us at the restaurant and the conversation was so easy. He was fascinating to talk to, I was enthralled with his Hollywood stories.

He would tell me a story about his friendship with Frank Sinatra (I was on the edge of my seat) and then he would say, enough about that, I want to learn about you.

I said, none of my stories will come close to yours. He said, doesn’t matter, it is you I am interested in. Wait a minute, it occured to me, this is a date!

During dinner, we started talking about writing books. He had just recently written one and he was telling me all about it. I was telling him I fancy myself a writer, but I write about my dating life. Ironically I say, also a comedy. He asked why I haven’t published it yet and I said, I don’t have my final chapter, you know, my happy ending.

He said, that is it. I said, what? He said the title of your book should be “My Happy Ending”. I said, that sounds naughty. He said, exactly why you should use it. It is an incredible double entendre. Hollywood has spoken. LOL

We have a great time, and he insists on walking me home. While we were walking, someone recognizes him. They yell out of their car, we are big fans! He waves. I said, I can’t believe those random people were my fans. He said, I think they are talking about me. I laughed and said, of course they are! I guess my comedy could use some work.

He gave me a hug and he was on his way. I thought we had a great time, but I definitely wasn’t interested romantically.

A couple of days after our date, I receive a copy of his book in the mail. He wrote the nicest note to me on the inside cover and ‘til this day, I cherish the book as it is proudly displayed on my coffee table.

He would continue to invite me to his shows in the Chicago area and I would see him when I could. I also visited LA and New York for work, and he gave me tickets to see Jay Leno and David Letterman’s shows. He was good friends with both, so I had the VIP green room treatment. He really knows how to make someone feel like a big deal.

A girl could definitely get used to this, but it wasn’t really fair to him. So, once he knew I wasn’t feeling the same way he did, he definitely started to pull back on the invites. I understood but enjoyed it while it lasted!

Lesson Learned? Ironically, if he was 20 years younger, he could have been my 'Happy Ending" (in my eyes anyway)! But I had many awesome adventures because of our friendship that I will always smile about. Perhaps his title will still come in handy some day when these stories become a book!