Dating at Fifty

In May of 2002, I made the decision to end my marriage.  Single for the first time in twenty-eight years, an odd thing happened.  The Universe placed a flashing neon light over my head brightly blinking, “Available!”

I began being invited on dates, meeting men at the most random places. They are as follows.

Jimmy.  I had known him since 2000.  We became acquainted at the Starbucks near my art studio.  In those days I could still hear and chatted up any and everybody.  It was early spring, one of those clear bright blue days heralding the end of a long gray Chicago winter.

Soaking up the sun, swilling my java, I noticed the guy at the next table reading the paper.  He glanced up and I asked, “What’s in the headlines?”  Shortly thereafter he asked to join me.  He then told me his wife had died in January.  After that, whenever I saw him, I thought, “Poor lonely sad widower” and spoke with him for a few moments.

Jimmy once brought his step-daughter, Amy, to see my studio.  Later he informed me Amy said to him, “You should marry that lady.”  It made me uncomfortable.  I avoided him from then on.

Fast forward to May of 2002.  I was walking out of Starbucks, crying.  Jimmy was walking in.  He asked about the tears.  I refused to discuss it.

The next time we bumped into each other I explained that I had just pulled the plug on my marriage.  He asked me to dinner.  I said, “There is no way I am ready to date.”  To which he replied, “It wouldn’t be a date.  It would be two friends having a meal.”  Smooth, huh?  I took that at face value.  I had next to no money at that point and eagerly grabbed every opportunity for free food.  Agreeing we were merely friends, I accepted his offer.  We had a wonderful time.  I wasn’t a bit nervous because it didn’t feel like a date.

The others:

Jewel Guy.  At Jewel Grocery Store, Barrington’s answer to Piggley Wiggley, I noticed a fellow choosing apples.  Several aisles over he approached me and asked, “If a man met a woman in the grocery store and asked her out, what would she say?”  I replied, “She would say yes, but only if she could drive her own car.”  Yay! Another free food possibility!

I drove to Chessies, a local watering hole.  The name is short for the Chesapeake and Ohio Railway.  One dining room is a vintage 1915 train car.  The free food was good, but when he called for a second date I didn’t accept.

Creepy Skin Guy.  I met him while in line at the Post Office. He asked for my number and later called, but I chose not to go out with him.  He had a weird skin condition, dry flaky unattractive flesh on his face and arms.  Not even free food was enticing enough to endure an evening gazing at his countenance.  Karma being what it is, several years later I developed a rash that lasted for years and made his disease pale by comparison.

Spiderman.  I shared one miserable evening with angry Spidey.   He had a spiderweb tattooed on his wrist.  When I commented he rolled back his sleeve, showing me that the web crept all the way up his arm.  He said everytime his ex-wife pissed him off he added more cobweb until at last his entire left arm was entangled.  He made me pay for my own dinner.

John.  I met him in the summer while sitting outside Barrington’s Starbucks.  He had ridden his bike from neighboring town of Palatine.  We had a lot of dates. I drank my first Dirty Martini with John.  He paid for everything and made me laugh. I introduced him to co-workers.  One maintained he was “light in his loafers.”  In retrospect, I suspect she was right.

Wally.   I encountered him at church. He was about one-hundred and thirty-five years old.  Wally shuffled along behind his walker, ogled me in the pew, hobbled up to me after each service and made small talk.  He asked me out several times. I finally relented and met him for coffee.  He was a nice enough guy, but I wasn’t looking to change anyone’s Depends.

Meanwhile, I was falling in love with Jimmy.  He was wonderful to me.  Jimmy took me on fancy vacations including a Caribbean cruise, a long weekend at an upscale Charleston Bed and Breakfast,  New Orleans French Quarter, San Francisco, San Antonio.  He paid for all of it and wined and dined me everywhere.  He held me when I cried during my long painful divorce. He included me in family gatherings.  He showered me with gifts.  And he made me laugh my sides out.

However, I was terrified of making a wrong decision.  Jim finally got fed up with my reluctance to commit and dumped me on my wishy-washy white backside.  He loaded his golf clubs into his silver Jaguar, pointed his car East and took off for parts unknown.

I missed him terribly.  I emailed repeatedly, called often.  He didn’t reply.  He didn’t pick-up.  He’d simply gone underground.  A prairie dog.  Wouldn’t even pop his head over the rim of his hole. Thankfully, at long last Jimmy relented.  He was walking along Myrtle Beach when he finally took my call.  As soon as I committed to him, the Universe turned off my blinking neon Available sign.  No one ever asked me out again.  That period lasted only a few months.  Curious, huh?

We were married in July of 2005.  He still makes me laugh, treats me gently, and buys me food. I’m very glad I lured him out of his burrow.