A couple of close friends know, one has his CHL, another is wanting to get hers, roommate is one of those people I don't WANT carrying!
when I got mine, my mom was bragging to a couple of her friends, they kinda had a shocked look on their face, I politely asked her to not do that EVER AGAIN! explained why and she's fine now. FWIW I think her friends have forgotten, but they are really cool folks.
i've been "spotted" once. clip on my IWB reflected some light and a family friend noticed it and came up and asked me about it. knowing him, and the fact that he straight out asked if it was a gun, I told him. He was 100% cool with it and has never brought it up again. even when i've been to his house to help his daughter with her algebra.
I don't broadcast that I carry and i'm not going to volunteer that I do, but if someone that I trust asks me point blank, I will answer them straight.