My roommate is pretty chill and not a bigot, but he is not familiar with the idea of genderqueer. I want him to know but don't want to tell him because it may seem so random. He has seen me in nail polish and knows I have experimented with bisexuality and not batted an eye, so I think he is open minded. Is it really important I have this conversation with him? We are not super close, but we are friends.
Hello! While it might not be that important to have this conversation with him, given that anyway it might not come as a shock or even new information to him in some ways, it might come up one day in another conversation and well, that's fine. In short I don't think that you have to tell him in a special "we need to talk" time. If it comes up, be honest with him, and if it doesn't, don't stress about it! He seems like a cool and open-minded person anyway. If he asks - just tell him. Alternatively, if one day you two have breakfast and run out of conversation topics, ask him "are you familiar with the idea of genderqueer?", and explain it to him. It'll be done, and out of your mind. Yay! o/
I think this is good advice because he must know I'm different in some way already, so I can express myself around him.
Honestly, once people find out you're gay or bi, all bets are usually off the table and people generally stop carrying about what gender-bending things you do. My straight friends have stopped noticing or caring if I like wear a pink shirt or something.