Jimmy had always been a loser. In every aspect of life, he did not succeed. He always bought 50 50 raffle tickets, scratch offs and lottery tickets. None of them were ever winners, not even a dollars’ worth. He never won the girl or got lucky. He worked a dead in job and still lived in his parents’ basement.

At 25 he had long ago come to terms with his lack of luck. He cleaned the floors of the local convenience store and was as happy as he ever could be with the small wage he received. The meager earnings kept him in extra chips, cola and comic books. He still had the original video game console that his father had gave him years ago, bought from the local thrift store. Yes, he was content.

Imagine his surprise when the call was for him. The lady on the other end congratulated him and explained that he had won their yearly sweepstakes. He didn’t remember which contest it was since he sent them all back and never heard of them again.

The perky voice on the phone informed him that he had won an evening, including a fully paid dinner with the person of his choice. Any person. Dead or alive. The company scheduler would be contacting him in a week to get the name of the lucky individual and with the evening’s details.

Aghast, he hung up, thinking it was just a joke. The goth girl clerk on the evening shift liked to smirk at him and he bet it was her pulling a fast one on him.
 
Even though he didn’t believe in his luck, his mind kept wandering to who, if it was true, would he spend the evening with.

His first thoughts included some of the hotter actresses he had ever fantasied about. The latest leading ladies, the female teen heartthrobs and even the current porn super stars. But after some thought, all were vetoed. After all, how could he, the ultimate loser, look one of these beauties in the face, especially knowing what his fantasy had included. Besides, no way he had won!

He later thought that if had won, why not dine with some great business man. Steve Jobs, Lee Iacocca, or maybe even Bill Gates. After much thought though he decided that they would only mock him and his losing streak. But then, no way he had won!

Mid-week he began to think that maybe if had won, a famous politician would be perfect. FDR or Lincoln, or Washington or maybe even Obama. But no, how could he face them and their accomplishments. After all he hadn’t even left his city, let alone his state or even the USA. Of course, it’s no problem because he hadn’t won. It was all a joke on him.

A week later his mother called him to the phone and when he picked it up, it was the same perky voice, asking for his decision. He muttered a name and was told that a limo would pick him up the next night at 6.

Not believing that this was real. He still prepared for diner. At 6 a limo arrived and after entering it, he was driven to the most expensive restaurant in the city. The Madre welcomed him and led him to his table. There sat the man he had requested.

He walked to the table and holding his hand out said, “Pete Best! How does it feel to be a bigger looser than me? The fifth Beatle? Yeah right.”