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This has been my strategy. I like to compliment people because I can remember the few times it's happened to me, but I'm not trying to creep anyone out. Mostly stuff like "awesome shirt!" or "hey, sweet hat". Never "nice cock, bro". And never with the intention of starting a conversation. Mostly like passing by someone and pointing "excuse me, love the boots.", then keep on truckin' by.
Heh i have a couple stories.
At costco picking up hotdogs for the crew, get back to car and notice older (60+) lady with Doc Martins on (i figure shes an old hippie but doesnt really matter) so i tell her i love your big stompy boots! And because of her style i add, "you may not but i think you would love Jon Fluevog shoes" she thanks me and says she has a couple pairs and loves them but doesnt wear them every day so they last longer.
Pleasant 45 second interaction.
At a music festival in victoria bc watching a metal band called Malahat, see a younger woman wearing the same colour converse shoes im wearing standing next to me, bamd pauses and i tell her she has terrible taste is shoes as im looking down and pointing to my own shoes. She was confused for a moment then laughed loudly enough security looked my way.
Have used the shoe bit a couple times stuck in close quarters (elevators hallways transit etc) a few times not always successfully but usually it goes over well when they notice im wearing the same shoes.
Sometimes i have to explain it was just an intentionally bad joke(i do love a bad pun and a good dad joke) but rarely usually is well received. But thats literally all i intend and it usually happens in passing.
(Middleaged white guy beardo)
I wish someone would drive-by compliment me with "nice cock bro"
Sorry to look twice, but wow, nice cock, bro.