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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)