How I Found a Date Worth Keeping

Have you ever found yourself stuck in an unsatisfying pattern of life with no clue how to change it?

 

My dating life wasn’t working and I didn’t know how to fix it.  I was still single in my 30s, approaching 40, and wondering why I couldn’t find someone who wanted to be in a relationship with me.  The women I was attracted to and interested in dating weren’t interested in me and vice versa.  I was successful in other areas of my life.  Why was I so unsuccessful in relationships?  What did I need to do to change?

Significant changes came to my dating life when I read best selling author and psychologist Dr. Henry Cloud’s book, “How to Get a Date Worth Keeping.”  The book is based on his work as a dating coach to his assistant Lillie Cashion.  Dr. Cloud offered to serve as Lillie's dating coach and then equipped her to tackle her dating life in fresh and challenging ways.

The book offers three strategies to revamp your approaching to dating and guarantees you’ll be dating in six months.

Here are the strategies and how I applied them:

1.  Get a team – I needed to surround myself with people who would support me in my efforts to change my approach to dating.  People who would cheer me on in my efforts and hold my feet to the fire if I got in any unhealthy relationships.

 

My primary team member was my counselor Michael.  At the time I began implementing Cloud’s strategy, I was in seminary. My particular degree program required me to receive six months of counseling.  I found it so helpful that I spent 18 months meeting weekly with my psychologist Michael, who also served as my dating coach.  He provided a safe place for me to go with any anxiety, questions, or issues that surfaced as I revamped my approach to relationships.

2.  Get out there – I stepped up my dating game significantly and became much more assertive in my efforts to meet women.  I joined e-harmony.com and looked for opportunities to meet women in my church.  At one point, I went out on coffee dates with eight different women in a two week period.  A well-meaning friend questioned my efforts and suggested that word was getting out that I was “playing the field.”  Honestly, I didn’t care.  I knew what I was doing.  I had no interest in being physically or emotionally promiscuous.  I was simply trying to meet more women to figure out what I was looking for in dating relationship and eventual marriage partner.  I knew I was heading in the right direction.  If people had nothing better to do in their free time than discuss my dating life, so be it.

3.  Get Healthy – Meeting with my counselor Michael was enormously important.  Stepping up my dating game caused some buried internal issues to rise to the surface, which is exactly what Cloud’s approach to dating is designed to do…it forces you to confront your issues so you can resolve them and move on.


You don’t need a paid professional to address the personal issues in your life that might be hindering your dating life (although in my case, it was worth the investment).  A good friend who shoots straight with you can also be of great help.  Michael helped me wrestle with the things in my internal world that were getting in the way of meeting potential marriage partners.  In particular, he opened my eyes to the ways my addiction to approval and my tendency to people please had the potential to derail me from meeting and pursuing a great woman.


Within eight months of reading the book and applying what I was learning, I met my wife Tracy.  Needless to say, I highly recommend Cloud’s book! 


This past weekend, I invited Dr. Cloud's former assistant Lillie, the subject of the book, to speak to single adults at my church about what she learned through her experience of having a dating coach and how she met her husband Audie.  She now serves as a relationship coach and executive coach.  You can listen to her talk by clicking here.

Me, my wife Tracy, Lillie and Audie Cashion

Were you ever stuck in an important area of your life?  What changes did you make to overcome it?