How do I tell my boyfriend I'm genderqueer?

This is probably something important to disclose early, especially if your friends know about it, and it seems like you think that as well.

I'm a straight man, but I do have a fair number of queer friends, and if I was dating a woman who revealed to me she was ambiguous about his or her gender, my biggest insecurities would be if she was still attracted to me (because so many young men confuse gender identity with sexual orientation) and if she wanted to start a medical process of masculinizing, because while I can appreciate a beautiful man, my interests are usually towards feminine or androgynous form... and for most men sexual compatibility is a pretty big deal.

Now from your post I gather physically masculinization isn't what you're after, but your guy might hit the eject button if he doesn't understand what you mean. But if he's cool, he'll understand that sometimes you just want to identify as a guy and realize that you aren't necessarily going to change what drew him to you.

It is a big part of your identity, so it's probably better to bring it up sooner rather than later so trust is secured, but to avoid scaring him, the best way to bring it up is nonchalantly in a private conversation to indicate a lack of urgency that tends to make some people worried they're being thrust into the middle of a crisis. A simple "so how do you feel about gender?" followed by something like "Yeah, I guess I can identify either way..." to indicate it's not a crisis, but is a facet of you that's important to you. But because he's a young man, it's probably pretty important for him to know that you aren't planning on changing the parts of your body that interest him on a more than friendly level.

He could still run, in which case he's probably not right for you. But if he is, he'll appreciate that some days you'll be his guy. That would work for me.

/r/TwoXChromosomes Thread