Dating Diaries…The Power of Our TRUE Stories

Last Saturday night I literally ripped myself from the Big Red Chair, having grown to it from a few days of taking time away from my work to “veg” and catch up on all the Oscar nominated films I’d been too busy to see. You have to know something about me…I am a film addict. There’s no 12-Step Program for it, so I find like-minded people to just binge on film with me. We go to matinees where almost empty theaters give us the feeling that we are SO BAD!  I don’t need to be a pole dancer to feel BAD…I’m easy.


There was an event sponsored by a new friend and Dating Coach colleague, Jessica that sounded like a great place to get some book material and spend an evening with a friend. A theater troupe called Playback Theater would be interviewing singles brave enough to come and even more courageous to raise their hands, volunteering to share their best and worst dating stories. The actors would then skillfully perform them with movement, an amazing World guitarist supporting them moving about the stage, talking, sometimes singing, but always trying to reveal the joy and pain of love stories. It was truly an amazing thing to see the power not only of love, but of telling our stories.


The volunteers were straight, gay, lesbian, people of color, men, women and the stories were ageless. One man met a woman online who seemed for all the world he said to finally “get me”. After emailing and talking on the phone, he made a trip to the East Coast to meet her. “It was probably the most expensive dinner ever,” he laughed. But, love was important and the risk worth it, so off he went. They sat down and began to talk and time passed, and so did the hope. She was a great woman and she got him. What wasn’t there was that “magic”, “spark”, “chemistry” that says “YES!”. Some would argue it might come later, or that it was too soon to tell. Could be. But most likely, they had all the right stuff of friendship and how beautiful is that! What it wasn’t, however was the same as finding a “beloved”.


He knew it and sadly, so did she.  He spent a night in the City and with a heavier step, left the following morning to come back to San Francisco. He could have “written a story” when they met and didn’t feel the Za Za Zoom. It might have read something like this…


Chapter 1: “Well, there we were. She was lovely and funny and I loved that she listened so well. Even funnier after a few martinis.  Her hair was beautiful and my, what an interesting job! We even liked the same kind of music. Even though I didn’t feel really romantically attracted to her, it might come and this seems good enough for me. I’ll bet she doesn’t drink like that most of the time…”


He flew home instead of writing the story. Sad, disappointed and not looking forward to swiping right and looking at yet more faces online,  he was willing to take some time to get through this and get right back out there and begin again! It takes courage to see what we see, trust ourselves about how we feel, be willing to feel all the feelings, the good, the bad and the ugly that seeking love will certainly bring, and yet to climb right back up on the horse.


I hope you will get the support you need to be out there in that dating world. No matter how old or young you are, many things are the same. We all want love and need to be ready and clear about just who we are looking for to share our lives in this chapter. Here’s to the brave singles ready for love and willing to do whatever it takes to find it. 

If you’re ready and want to “up” the chances that you’ll find that special someone, get the support you need and enjoy the experience of dating, I can be your guide.

Call me at 510-817-4242 or email me at

for a Complimentary Strategy Session to see if we’re a good match!

Donna Bailey, MS

Coach, Speaker, Writer and Expert in Dating and Relationships for “Grown-ups”

Donna’s Big RED Chair


  1. Jessica Engle on February 21, 2017 at 10:25 am

    Donna, what a lovely retelling of our night on Saturday! And you’re so right — how courageous one must be to put their heart out there not knowing what the result will be. Thanks greatly for the compassionate work you do and for supporting myself and San Francisco Playback Theater. Til the next Dating Diaries!

    • admin on February 21, 2017 at 11:09 am

      This kind of work is so important and events that bring people together who are single and can feel alone in the search for someone are crucial. Thanks for organizing this amazing event, Jessica.

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