Solitaire

Dating Myself One Week at a Time

How did I get here?

In 2016, I published an award-winning book called Joker to King in which lessons on becoming a healthy adult were arranged according to the 52 cards in a playing card deck. Fifty-two cards in a deck and fifty-two weeks in a year to practice all fifty-two lessons.

Then, in 2019, I got divorced.

I began work on rewriting the book and building a better relationship with someone new. I remarried in 2021, and the second edition of Joker to King was also published in 2021.

Then, in 2024, I began the divorce process again.

Two marriages. Two divorces. What was I doing wrong?

After a LOT of therapy and a LOT of writing and soul-searching, two epiphanies struck me like twin bolts of lightening.

The first epiphany had to do with my role as a husband. After graduating college in 1994, I have always had roommates. I never dated around before…I’ve only been in long-term committed relationships of a year or more. My entire adulthood, from the 1990s until now, has been defined by my relationships with other people. For about three solid decades, I have developed this habit of diving headfirst into relationships quickly. And I go all in, wrapping my identity and life around my partner. I never lived alone. I never learned who I am outside of a relationship.

The second epiphany had to do with my role as a teacher. After graduating college, I immediately began work as a teacher. I have worked with all types of students in all types of learning environments. I have done almost everything I could possibly do in the education field: I taught continuation high school for kids on probation working toward their GED; I taught middle school and high school math; I coached high school basketball; I taught English and public speaking and education courses for four different colleges; I worked as a program coordinator, an academic dean, and even a teacher for an outdoor environmental education program. I never worked outside of education before. I never learned who I am outside of my relationship with school.

The Idea Behind Solitaire

At the end of September, my wife moved out, and for the first time in my adult dating life, I was by myself.

I have always lived my life defined by three distinct roles: being the perfect father, being the perfect husband, and being the perfect teacher.

My role as a husband fell apart now that I’m no longer married. And with the loss of my wife’s income, I began to really struggle with bills. I have full-time physical custody of my kids, and now my role as a perfect father began falling apart because I couldn’t find a way to pay bills and adequately provide for my children. I couldn’t face my students at work, I couldn’t teach, I began cancelling classes, and my role as a teacher began falling apart.

I was desperate. I was feeling the familiar pull to dive headfirst into a new relationship. My birthday rolled around (October 30th), and because I was about to turn 52-years-old, an idea hit me. What if I revisited the Joker to King structure built on the deck of 52 playing cards? There are 52 cards in a deck of playing cards, and there are 52 weeks in a year. What if I went on a new date with a new woman each week? Fifty-two dates with fifty-two different women, one week at a time, for an entire year? I start at my birthday in 2024, and I end at my birthday in 2025. Perfect…right?

Wrong.

I went to one of my favorite restaurants nearby, sat at the bar, and ran this idea by my favorite bartender. She explained that this was a terrible idea, and that I was falling into old habits. I was doing it again. I was trying hard to find a new partner to wrap my identity around. My bartender friend then suggested to take myself out on a date. Just go to a restaurant that I’ve always wanted to try and go by myself.

I didn’t need to go on 52 dates with 52 different women for a year. What I needed was to spend the entire year getting to know myself. I already know who I am in the context of a relationship. I don’t know who I am without one.

That’s when the idea for Solitaire was born. So on October 30th, my 52nd birthday, I wrote out the plan to go on 52 dates with myself for the next 52 weeks.

A Year of Solo Dating

First and foremost, I’m a writer. This is a fundamentally a large long-term writing project. I am using this blog to document my self-discovery journey, while seeing if I can make it out here in this world as a single man in his 50s.

Each week, I am going to go someplace new, taste new things, experience new pleasures, revisit old passions, and live my life in wild, fun ways.

I started on my birthday week 2024 and will end this project during my birthday week 2025. I haven’t planned each one of my solo dates yet, but I do have a list of places to visit, restaurants to try, activities to do, and passions to pursue.

There’s a book at the end of this tunnel, and if I do this thing fully, I will hopefully find myself at the end of that tunnel as well.

Please read and enjoy. Feel free to use the contact button below to reach out to me with any thoughts or suggestions or encouragement or comments of any kind.