I was married for my entire adult life, from the tender age of 20. We started seeing each other when we were 18.

My story is a very familiar tale of a young couple that struggles to build a successful life and family, but later self destructs in middle age in a very stereotypical way. I was married for 24 years and my divorce was finalized in 2017. I won’t go into the details of my marriage failure in this blog because it’s more about my journey to start my new life and to discover who I am apart from the person with whom I spent the majority of my adult life.

The marriage ended badly and it was a brutal battle to try to save any hope of keeping it together. When it ended, I felt like I was ready to start fresh and build my new life. I was really excited to reconnect with my friends and to start venturing out to meet new people…to start…dating.

I was 44 and had never dated. This last year of dipping my toe in the dating water has been eye opening. I don’t have any horror stories to share. I also haven’t been much of a dater up to this point. I’ve met a few really great people, not all love interests, who have helped me to learn a lot about myself.

I’ve learned that I am still full of shrapnel from the battle that I fought. Pieces of it come out when I least expect it and it’s hard. I used to feel so sure of certain things and secure in that and in myself. Now, I just feel not secure about much of anything. I used to be a master of tuck and roll. I loved a little uncertainty because I liked to go with the flow to see where I’d end up. My Tuck and Roll has rolled away (temporarily) and now I just feel like a triangle…a wedge of Swiss cheese. I feel a little stuck and full of weird and uncomfortable holes.

I love to read Shel Silverstein to my boys before bed. We were reading “The Missing Piece Meets the Big O”, which is about a triangle sitting around waiting for an incomplete circle to roll by and pick it up so they can roll off into the sunset together. It rolls with some different circles, but things don’t work out. The Piece meets the Big O (O) and sets out to try to roll by itself because of what it learns from O. The Piece eventually changed its shape and rolled away happily with O. The two whole and fulfilled O’s shared the joy of their own rolls together.

This is what inspired me to do these dates with myself. I need to get my sense of fun and adventure back. I need to become whole on my own and learn to just relax and let things be whatever they will be. I need to enjoy the good and learn from the not so good and move on. I need to shake the dust from the battle out of my hair and know I have a lot to offer and just embrace this new chapter in my life. Hopefully, this experience will slowly help me to fill the holes and allow me to start rolling again. I’m not going to abstain from seeing the male species. This isn’t about being mad at men or mad at dating.

The rules for this adventure are pretty simple. The only reason for them is to keep me excited and motivated to continue to #50 and to keep it fun and interesting to write and read about. I’m going to do my best to not repeat the same type of date more than once. The dates must put me pretty well outside my comfort zone in some way and they must be fun. That’s it.

Stay tuned for The Kick Off…