Married at 30 and then divorced at 42, I arrived at mid-life no more prepared to date than a 14-year-old schoolgirl. First, when I was in my early twenties and supposedly at the height of my powers of attraction, I was weighed down by about 20 extra pounds and a rock-bottom self image.But there I was, a schoolgirl with crow’s feet, a mortgage and two kids — heading out into the dating world. Since then, I’ve had some disappointments, a lot more fun than I ever expected, a few very late nights, some long talks, a couple of promising relationships and finally a relationship that held more than promise, but through it all, I’ve learned a lot—about myself and about dating in the Middle Ages, or at least, in my middle age. Then I lost the weight (but not the low self-esteem) and spent about half a decade embroiled in a tragic, long-distance relationship that always seemed really tempting when we were hundreds of miles apart and then a monstrous mess when we were in the same city for more than 24 hours.Once you get over it, I have to say it's pretty fun.
But while I’d grown older and my wardrobe had grown shabbier, I’d also sprouted a semblance of self-esteem and confidence and — I’m not saying this to brag, just sharing information with readers who may need it — apparently this shiny self-esteem stuff seemed to count for more than youth ever did because, oddly, men were more interested in me than they had been when I was in my twenties.
At 65, my date (I’ll call him Jerry) was a few years older than me.
We’d been introduced by a mutual friend who thought we would be a good match.
Jerry was a wealthy, highly successful, intelligent, divorced chap who worked in the film industry.
He owned four homes around the world and, on paper at least, ticked every box going. He was scruffy with a scratchy-looking grey beard that made him look horribly unkempt.