I don't think either of these men were working with olive trees. The first guy was eating at a taverna in Gonies with 2 other men. My thought was that they were 3 businessmen that met for lunch, which seemed to turn into a longer lunch. (They were brought several litres of wine and got a little loud.) I figured, at the time, the one guy was just being silly.

A day or so later, we were in Stalida for lunch. The whole town was pretty much closed up for the season, but there was 1 bakery/cafe that was open. There were several men customers, some with friends, but there was one man sitting alone. He was also dressed business casual (polo shirt, khakis), he may have been mid 60s. He had a small handful of olive branches over an ear as well. (It was not the same guy!)

The few times I ate at restaurants not at my hotel, I noticed that customers were always all men. The only women were the waitress or cook. Women were out but shopping at a grocery store, while the men were sitting around drinking coffee and chatting.