What if you woke up on the eve of your 39th birthday… suddenly single… and you’ve only been with one woman – literally – your entire life? How do you enter the dating world? Where do you begin? And quite frankly… what are you even looking for?

This is my dilemma… realizing I know everything about one woman… and nothing about the rest.

So I've given myself a goal… to date 50 different women… before my 40th birthday. Is it ambitious or unrealistic? I have no idea. I just know I have a lot to learn… and mostly… about myself.

This is my story.

50 before 40.