Confessions of a New Age Player

I'm just an average guy who re-entered the dating world back in 2007 after being married for over 10 years with no clue about how much things had changed thanks to the Internet and online dating. To put it in perspective, from my high school years through my late 20s, I probably went on less than a dozen first dates. This was back when I was considered above average looking, had a full head of hair and a tight body. Fast forward, in my first three years as a divorced man in his late 30s / early 40s with a receding hairline and a few more inches around the waist, I went on over 100 first dates. The difference? Online dating! Once you get over the "Am I really so desperate that I have to resort to meeting strangers on a website?", it actually works.

Along the way, I would share my dating experiences with my closest friends, who found my adventures and perspectives in dating to be hilarious. Keep in mind that for the most part, I agreed to meet just about anyone that weighed less than me (yes, I'm shallow) and I'm not always the most politically correct person in the world. They found my stories to be so entertaining that they talked me into writing about them. The names have been changed to protect the innocent as well as save me from potential law suits and death threats. But they are listed in the order they occurred, and for the most part, I believe they illustrate a change in my personality over time.

And as a guy who has went on so many dates (no exaggeration...well over 100 in three years and still going), I've kind of got this thing down to a science. I provide tips for newly single people, and yes, I get the irony of someone who has went on over 100 dates in three years saying he has it all down. But while I'm very good at getting first, second and even third dates, I've never claimed to have the whole sustainment thing down.