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My dad did the same. He’d always ask me why I don’t have a girlfriend. When I’d choose inside chores over helping him pull weeds or whatever, because it’s hot outside, he’d ask me if I wore a maids dress while doing it to try to pressure me into doing more “manly” work.

The funny thing is that when I hit ~20 years old I think he had a realization on his mind that I was actually gay and changed how he acted. I’m not, I’m like 90% straight, but he’d try to do little things to show his support for my presumed closeted gayness. For example, I had a close male best friend. Before we hung out he’d awkwardly hand me $50 and say, “I am glad you are happy, take him out for dinner and a movie on me 😉”.