Honesty Has Scared My Dates Away


Honesty has scared men away. When creating my profile on Match.com, I was being honest when I said, “I don’t brush my hair everyday”. Honestly, it’s in a ponytail and it’s fine. And honestly, I really don’t care about taking long walks on the beach, holding hands and listening to the midnight rain. For a first date, I honestly, don’t want to suffer through a candlelit dinner, honestly, I’m happy meeting at the gas station.

When I tell men I went to prison, they usually are intrigued and want to know more.  Yesterday, I told a guy the quick version of my story and then he proceeded to tell me about the time he went to jail for 20 minutes and his high school buddy was one of the largest drug dealers, went to prison and is mafia.

Another date shared his entire life with me. Well traveled, countless accomplishments and accolades. He was remarkable, there was no disputing.  He had lived an extraordinary life, if he was being honest. I was engaged as an active listener, yet found myself examining my own thoughts as I listened to him. I was listening to two people, my own thoughts about him and myself.  His monologue was hinging on exhausting and falling into a coma, my vodka martini helped, maybe two martini’s helped, I can’t remember.

He eventually took a moment for oxygen and to guzzle his beer, so I quickly said,”I went to federal  prison once”. He responded, “Wow, I thought I had the best stories” “You just one-upped me”. Then he proceeded to tell me about the time he was arrested for beating up some guy when he was younger.

The minute I saw him, waiting in the bar for me, I knew. It was that feeling you get, the tummy twirling, heart racing, an unexpected excitement. I liked him, what a relief to know, there was still hope!  I barely tasted my dinner, he had nice hands, a great smile, he was athletic and toned, there was something sexy about him.

He told me about his life, growing up, flossing his teeth, mowing the yard, and the strong work ethic instilled in him as a young boy.  His father was hard on him, but it paid off in the long run.  Today, he credits his dad, dedication and hard work to his success.  Work was his “other woman”, his lover, his identity.

“Holly, tell me about yourself”. “Do you want me to go back to childhood, or most recent”?  His said, “How about now”. Wondering if this was a trick, I asked if he had researched me.  It turns out, he hadn’t.  In fact, he would never have asked me out, if he had known I lived in the “big house”.

It was difficult for him to process and based on the questions he asked, I suspected things had changed.  It was confirmed the next day, through a text message.  “I’ve worked hard all my life and I don’t want to be affiliated with you, because people will judge”.

While honesty isn’t always easy, it does give others permission and a sense of comfortability to share their story, maybe the one they have been hiding. On the other hand, honesty may put others at a distance.

Prince Charming hasn’t found me yet, and I will continue to be honest and take ownership of my own story. Fear of rejection and judgement are painfully part of humanity, it’s not pleasant, but it’s not fatal.









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