When does trolling for chicks become creepy?

I ran into an old friend from my single days. Nice guy. A pretty boy in his prime who had gals flocking to him in droves. He still looks good at 40.

My family was at the Farmer’s Market doing the weekly shop when I spotted him with two other single guys. I turned to my husband and said, “Do you think he’s trolling for women at the Farmer’s Market?”

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In the banding together men do when it comes to all-things-trolling my husband stuck up for him, “There’s a lot of nice, wholesome—and good looking—women who work here. It’s a great place to meet someone.”

Yes, if he’s interested in meeting someone twenty years younger than him. Which apparently he was. He and his friends went from stall to stall doing a friendly and harmless chatting up of those wholesome gals.

Watching this unfold I was filled with a mixture of both pity and envy. He had been up to the exact same shtick when I hung out with him ten years ago—he and two ‘wing men’ went out every week looking for fresh faces. In fact, he’s probably been up to the same tricks for twenty years.

Catching myself in this judgment, I felt completely old and prudish. Can I already be at the stage of, “If I can’t have fun then no one else can either?” I’m only 42.

This is precisely something my mother would make a disapproving comment on. In my youth I would take pleasure scorning her for being uptight, not letting people live and let live, and all that.

Still when does trolling for chicks become creepy? And why am I dwelling on how he chooses to live his Peter Pan lifestyle (…oops, there’s another judgment popping out my now old and prudish brain).

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Me and my carefree single friend are living two very different lifestyles—by choice. And if I was being completely honest with myself, seeing how much fun he’s having makes me long for those days of nonresponsibility and easy, carefree sex.

Perhaps if I was single rather than bogged down in family life, I too would be at the Farmer’s Market trolling for fresh faces. Because really where does a 40’something meet ‘wholesome’ people?