"This guy is named Josephine, which is a problematic name for a man"
I had a good buddy who's name was Gail. I saw nothing wrong with it, but he hated his parents for giving him that name.
I would never give a child a name that was unusual, or even less than common for someone of that gender.
I used to work with I guy called Les, everyone thought it was short for Lester. It wasn't. It was short for Leslie.
For some reason, I was the only person he knew who could call him Leslie, and not have it bother him.
Go figure.