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^^ He gets together with Kuro around chapter 170, so there's your landmark.
^ Glasses guy only appears for like 2-3 chapters out of the entire thing so far. The first chapter then somewhere in the 200's when Kaito coincidentally runs into him when visiting another country.
As for other male characters... There are very few of them in general and none of them have regular appearances. Other male characters off the top of my head are a Lich that's the owner of the world's leading magic tool production company, a blue ogre (married) that's another of the people Kuro raised, the king and prince of the country Kaito stays in, and Jieglinde's dad.
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