Why the names of cities? It makes the ad look like one for a hotel or boutique chain.
In this world, everyone wears the same colour of swimwear. Except for The Man Who Reads Playboy!
Ooh a trade ad! I wonder where this ran.

Also, 8 or more air trips. Even in 2012 that still sounds like a lot to me :/
I'm pretty sure this actually appeared in the magazine itself. They had a whole series of these ads encouraging their readers that reading Playboy set them apart from the rest. It probably helped boost subscriptions, I'm guessing.
How many 18-year-olds were taking eight or more trips per year? I guess if his parents work for the airlines.
Is it wrong that when I read "A man who goes out of his way to find that special place" I thought
"What, the G-spot?"