Four years of failing

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Four years of failing, and I’m not just talking about the Trump administration. From April 2018 to December 2021, I had dated 54 women with basically nothing to show for it.

I didn’t date nor have a girlfriend until I was 21. That was due to lack of trying. I was a fat kid with no self-esteem. There was no way that anybody was going to be attracted to me, so I didn’t even try for fear of rejection. Then I went away to university, lost a bunch of weight and finally found love (or what passed for love at 21) for the first time. It lasted for about six months, but I had finally gotten my feet wet, so to speak. After a few more awkward attempts at love, I met my first wife about six years later. We were together for twelve years and married the last six of them. My divorce was finalized on my 40th birthday, and I truly embodied “40 is the new 20”. I knew who I was, and I knew what I wanted – and love wasn’t on the list. And then along came Jean. We met on a crazy blind date (dot com) and we were together for nine years. Love found it’s way back to me. I never felt like being with her was work or difficult. Life with her was fantastic until her Breast Cancer came back in late 2016. She died July 2017.

I know that love isn’t a commodity. You don’t walk into a store and pick one off the shelf. If love is to be real and meaningful, you can’t wish it into existence. But it was so easy with Jean, that I didn’t expect it to be be so incredibly difficult now. I did not have an expectation of finding another Jean. In fact, I felt like I was open to finding something new and different but satisfying in whatever way possible. What I didn’t take into consideration was the fact that things were different now. I was in my fifties. I was living in a new country.  And while we share the same language, Irish culture and society is different from California culture and society.

Was I not Irish enough? Was I too American? Was I trying to be somebody I wasn’t? Was I meeting the right women? Did I choose the right place to live? Was I ready to date as a widower? Will I ever be ready? I had a lot of questions for myself, and few answers. Through all of this self-exploration I determined that my best path forward was to be myself and do whatever felt right. This wasn’t much different from what I had done the past four years, but I wasn’t going to beat myself up for past mistakes and missteps.One thing is for sure, I’m not capable of making somebody happy by being something I’m not. I love myself, and I’ll find somebody who I love that loves me for who I am or die trying.

As 2021 was ending, and I realized that dating in my fifties was a Sisyphean struggle, I decided to document my efforts. Perhaps I would learn something from looking back at the previous dates. Perhaps I would help some other poor sap from making such a colossal mess of himself. Either way, 50 First Dates at 50 was created as a cautionary tale and a hope for the future. From here on out, the dates will be from 2022 (and beyond?)!