Dating Over 40: His Old Girlfriend -It’s a Small World

I just got back from a few days on Cape Cod – a much needed vacation.  We went to Provincetown and it didn’t fail to entertain and surprise us.  Turns out it was "Leather Weekend"  -how fun!  My favorite sight was two very tanned fellows in a Mercedes convertible with the top down, of course,  Each man was holding a brown dachshund on his lap and each dog had on a tiny black leather visor.  Honestly, I can’t remember how the men were dressed after seeing those dogs!

While walking around town, Paul told me that he had dated a woman who lived and worked in Provincetown during the season and came to the Connecticut shoreline during the winter months.  He met Diane in a bar about 15 years ago.  His memories weren’t so good – seems she wasn’t so nice to him.  Oh well, water under the bridge.

In the morning we stopped at the nearby sweet shop to get coffee on our way to Race Point, my favorite beach ever.  The  woman behind the counter was VERY friendly offering us linguisa (Portuguese sausage) and egg sandwiches which we declined thinking we’d come back after our walk.

The beach was deserted and fabulous. Then we had to hustle because we wanted to get breakfast and I had to shower and pack – all in one hour before check out time!

Paul said he’d go get the food while I showered which would be a big time saver. He came back with two egg sandwiches and a little bit on his face too.  Turns out Diane behind the counter WAS THE WOMAN HE HAD DATED so many years ago.  She had recognized him the first time in.  He thought there was something about her that seemed familiar, but wasn’t sure until he saw her the second time.

Diane and her husband own the sweet shop which is really a great place.  After Paul had ordered, Diane said to him, "We know each other don’t we?"  He smiled shyly and admitted, "Yes."  They talked about how long it must be and Paul told her what a great place she had. Not much more was said. What a small world huh?

Paul, who never forgets a face by the way, was stunned by cosmic collision.  He said she looked different – she used to have long curly hair and wore lots of makeup.  Now she’s more casual with straight and silver highlights.  Who knows if anything would have been said had we returned together.  Better than running into any of my old flames is all I have to say!

My favorite bumper sticker noted on the trip – "I ran into my ex, so I backed up and ran into him again"  OK, violent, but pretty funny.

Single for too long, Ronnie wanted to find love. So, she made a few tweaks and then dated 30 men in 15 months to meet her adorable husband Paul. Discovering the keys to midlife dating, she founded It’s Never Too Late for Love to help other smart, successful women find love too! Her mission is to share her proven dating advice  and keen insights about men with women everywhere who are serious about finding love with the right man. Ronnie Ann Ryan, MBA, CCC is a Certified Coach who has helped 1,000’s of midlife women with her Love & Dating Coach services. She’s been featured on BBC’s 5 Live Radio, NBC, ABC, and Fox News, NPR, eHarmony,,, Connecticut Magazine among others around the world. An established author, you can find her 6 books on Amazon.

Leave a Comment