Brains, Beauty & Balls...As Rare As Finding Moby Dick?

I was going through an old file cabinet yesterday and found an external hard drive that I used back in the day.  I hadn’t seen or used that thing in many years.  It’s a 1TB drive and my son asked if he could have it so I told him he could once I cleared all the old files off.  So, I plugged it in to see what data was on there and found a folder titled “Dating”.  I had forgotten all about that. 

When I reentered the dating world I was a big fan of using online dating sites like and others to help me find the new Mrs. Jake.  I knew that trying to find the perfect woman for me would be like looking for the rare white whale.  They exist but they are very rare and tough to find.  Simply stated, I wanted the Holy Trinity, Brains, Beauty & Balls. 

I was looking for a woman that was feminine but not prissy, able to fit in no matter if we found ourselves at a corporate dinner, around a campfire with friends or at the bar doing shots.  Someone that had a great sense of humor, was successful, professional, confident, honest, respectful of traditions, and socially conscious.  I wanted a woman that was devoted to family, sensible with money, responsible with possessions, compassionate, and capable of having detailed and informed conversations about trivial as well as meaningful topics…oh and she needed to obviously be single, live close by AND she needed to find me irresistible.  That’s not asking too much is it?  When you consider all of these “asks”, the notion that I would meet her in a bar or at the grocery store or stumble across her randomly in my day to day life seemed ridiculous to me.

Looking back it’s funny because I was pretty methodical about my search and efforts.  I knew what I wanted, I knew I was too busy to spend a bunch of time with all of this and I was also unwilling to allow myself to become overwhelmed, succumb to online dating fatigue and check out of the process all together.  Having said that, I realized pretty quickly that I was sending and responding to emails and flirts, answering questions, asking questions, etc. and up to a point, all of them we either identical or very similar.  Being someone that is “ambitiously lazy”, I decided to do some initial heavy lifting so that I could simplify the process.  I created a Dating Playbook to help with this.  It was a collection of emails (initial inquiries and initial responses), FAQs with answers as well as my FAQs to be asked.  It took a bit of time to compile all of this but in the end it saved me a ton of time and made the process very efficient. I literally did a copy and paste with this content and quickly moved on with my day.  After the initial stages of back and forth, I was able to determine quickly if we had a possible compatibility match and at that point I would move to unique communications.

In the end, this process worked out very well for me.  I found my four leaf clover and we are happily married and going strong.  If you are using online dating, hopefully this info can help you.  If not, that’s cool too.  Best of luck!

An Email Example:
Hi my name is Jake. I saw that you stopped by my profile but didn’t say hello so I figured I would break the silence. You’re very attractive so your photos caught my eye but your profile prompted me to write. I’m interested in having a conversation and hope you are too. Looking forward to hearing from you soon.