That's a really interesting question...
I concealed carry almost every day. I have a license, etc., so it is legal.
However, I also know that the presence of a gun is a problem for some people. So, for example, I talked to my massage therapist about it. Told her I carry. Asked about her opinion. And we came to an agreement. She is creating a safe space for me to be naked and vulnerable in, and I want to respect that, and not harm it in any way.
Now... if I was going on a first date with someone, I need to consider some things:
Option 1: Do I tell them about it so we are completely up front and honest about this? Starting off on the right foot?
Option 2: Do I not tell the person, since this is just a first date, and we don't really know where this is going yet.
If I take Option 1, then I risk alienating the other person immediately. Or, possibly start off a new relationship on a really strong foundation of trust and honesty.
If I take Option 2, and the date goes well, and there is another date... do I tell her then? After the 5th date? What if it gets down to heavy petting and she stumbles across it? What if I wait until I "feel something for her", and tell her then... and she's completely turned off? Then we both get hurt.
Obviously, this depends a lot on how the conversation comes up.
"Don't worry about a thing, little lady. I can protect us." (Pulls back coat to reveal concealed weapon.)
"I think it is important to be up front and honest with you, so I'd like you to know that I regularly carry a concealed weapon. How do you feel about that?"
... are very different conversations.