How should I come out to my friend when I'm afraid he'll take it badly?

Q: I want to come out as a trans guy to my best friend. He's a cis guy and most definitely what people would call a Chad. I know how this sounds but he's been my best friend for years and I'm so scared he'll take it for the worse.

S: I'm so sorry; that's an incredibly difficult situation. These are super valid concerns. We wrote about a different type of coming out to a friend here, and some of that might be helpful.

Do you know anything about your friend's (I'm just going to call him Chad) knowledge and thoughts about trans people in general? If this isn't something you've ever talked about, starting there would get you some information about how he might react before mentioning your own identity. If there are any other trans people he knows, how has he responded? Are there any trans or gender diverse performers/athletes/writers/etc. who you've heard him talk about? If not, you could bring something like that up. There are plenty of conversation starters that have nothing to do with your own identity: the rise in anti-trans legislation, trans celebrities coming out, etc. Or you could suggest a watching a show or recommend a book with trans and gender diverse characters/themes so you can talk about it. "What do you think about..." or "I thought this was..." are some ways to raise the subject. If Chad reacts badly, you'll learn a lot; if not, you've at least introduced gender identity as something you two have talked about a little, which will make it easier to come back to. And the next conversation doesn't have to be about you either; it can be a continuation or variation of the first.

Something else you can think about is what you would ideally like from Chad. A lot of people just don't know how to respond if they're not used to being around openly trans people, so if/when you do talk to him, consider letting him know specifically what (if anything) you're asking him to change. Name? Pronouns? Do you just want him to know? Are you out to anyone else, or does he need to keep it private for now? Do you want to be the one to educate him about gender if needed, or do you want to suggest some resources for him to learn from on his own?

The last thing I'll say is that you should protect yourself first and foremost. Violence against trans and gender diverse people is a very real issue. If you do get any indication that he would respond badly, think very carefully about what you want to do with that information. It is not worth keeping a friendship at cost of your own emotional or physical safety.

K: Seconding everything said above by S. Coming out can be really scary, and it sucks a lot to worry you'll lose a friend because of their beliefs. If you haven't already, I do strongly suggest getting a feel for his opinions and beliefs on trans topics and other trans people before coming out. In the past, I've done this by mentioning an article I read recently or a trans character in some show I had seen. For me personally, I made sure to keep my statements and opinions consistent with what I already knew (so, not pretending something was new to me if it wasn't, and not pretending I didn't have an opinion already) because if and when I came out, I didn't want them to feel like I was lying while trying to gauge their feelings. That being said, everyone's approach is different, and your safety is more important than anything else. I do want to add that it's not really possible to predict someone's beliefs on trans and gender diverse people based off how they come across (so your friend being somewhat of a Chad doesn't necessarily mean he'll react poorly). I know plenty of punks and leftists who were surprisingly intolerant of gender diversity, as well as people who were pretty cool that I would have guessed otherwise about.