On My Way Home, I called 'Crazy Old Man Pappas', a Local Dating Expert...

Shutterstock Images.

Inevitably, everyone gets old, if they're lucky. Some people give in gracefully, while others battle to the bitter end. I fall somewhere in between. I’m a realistic resister, but I know my limits.

The mirror may lie, but the camera doesn’t. You wanna know how the world sees you? Take a selfie. It makes your nose look bigger, which in my case isn't very flattering, but selfies don’t lie.

Reality checks can occur anywhere, anytime. I was out for lunch in a nice restaurant with a female friend who was in her mid-fifties when the waitress, a woman my age, asked her, loud enough so I could hear, if I was her father, hoping to embarrass us both.

When Michelle answered, “No. He’s my boyfriend,” the waitress asked how much older than her I was and how long we’d been dating. Michelle looked the nosy server in the eyes and stuck it to her, “He’s ten years older than me, and we’ve been dating for over a year…”

After taking our drink order, the disappointed waitress was walking away when I got her attention and asked, "Can you also bring me a Geritol on the rocks, please?" adding, "And while you’re at it, pour yourself a double-"

She later came clean about having been married twice and that both her husbands died. After her second husband died, she re-entered the dating scene, and she said that by then, men her age were only interested in younger women. I was hoping she wasn't gonna slip poison into my drink and add me to her trophy case…

Recently, I was having a nice conversation with an attractive young woman seated next to me at an event in a popular Boston bar. She was young, in her late thirties-early forties, a single mother, and the perfect combination of sexy and adorable. Great hair, nails, smile, and dressed to the hilt! Then, mid-conversation, out of nowhere, she switched gears and asked, “Are you retired?” 

Well, throw cold water on me and forget about my feelings! I was only looking to massage my ego, no other body parts. In retrospect, she may've been in the market for a daytime babysitter, and she was smitten by my trusting face and calm demeanor. I had had a few…

On the drive home, I called my friend and confidant, Crazy Old Man Pappas, a local dating expert, to tell him what happened.

When he heard that this young woman seemed sincere (eye contact) and even a little flirty (several hair flips), he said her body language didn't accurately reflect her intentions. He said she was a dating conundrum and too young for me anyway, and that I shouldn't take it personally. That she at least trusted me enough to watch her kids. I put Crazy Old Man Pappas on speed dial…

The long-standing formula for the youngest woman a man can date has always been the man’s age divided by two, plus seven. Maybe it needs updating. Once a man reaches 40, it should be half his age plus 10.

I met a woman my age online, and like me, she's a widow. We were having a great conversation when she suddenly announced, "Something doesn't feel right," and accused me of "Impersonating Vindog". Even after I cleared it up and got a sincere apology, I wasn't interested in her anymore. Maybe she had good reason to be paranoid, but I didn't want any part of that. I thought I was flying in a drama-free zone. Apparently, that no longer exists in the modern dating world.

Another woman, well within my age wheelhouse according to the formula, listed herself as from Norwood, and when her address suddenly changed to Foxboro, I asked if she moved. That's when she accused me of stalking her. And then I got paranoid about being questioned by police for simply asking a woman if she moved. It seemed like she wanted to play the victim in some weird, deranged drama she created and wanted to star in. I immediately blocked her! I wanted no part of that.

I’m looking for a female companion for conversation, lunch, dinner, movies, putt-putt, concerts, comedy shows, sporting events, and some hiking. That's it. If she can awaken some of my sleeping body parts, well, that's on her. 

Although my intentions are pure, I'm definitely being misunderstood. Now, after some initial experiences with the opposite sex in the dating environment, I’m not sure I really need or want a second bite of the apple. (Although I do love apples, metaphorically speaking)

Maybe I'll just get a dog…

Alone again, naturally…