Frumpy Middle-aged Mom: I might start dating again, if I only remembered how

I’ve recently decided to start dating again, after a very short dry spell of only 20 years.
My last date – and this is the truth – showed up at the door of my tiny apartment in Laguna Beach as a blind date, wearing ratty shorts, flip-flops and a T-shirt with a hole in it. A noticeable hole.
It was a blind date. He was a fellow journalist and we’d been fixed up by friends.
I asked him, “This is how you impress a potential date? Wearing a shirt with a hole in it?&rdqu