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How can you gauge whether someone is safe to come out to or not? 

Just want to add to what @Bre-RO said -- not everyone in the community can be a safe person. Unfortunetly, I've seen a lot of gatekeeping and discrimination within the community itself, so even that can be a little tricky. But yes, generally if you trust them and they're a vocal ally/ member of the community, then yes! You can also 'tease' it to test their reactions, i.e. saying things like 'it's cool [celebrity] came out!' or even things like 'look at this rainbow bag I bought!'.