This is a topic I've had to deal with rather recently.. The woman I'm with right now is great.
I don't carry all the time. I don't carry at bars, which were the setting for, well, most of our 'dates'. So in those instances, it really hasn;t been an issue. She knew pretty early on that I was into guns since I post pictures of my targets on myspace occasionally and it came up a couple of times. But I do carry when I go on the road.
So this past week when we went camping, I was carrying my 4" 1911 iwb the whole drive up. I was carrying it when I picked her up. I was carrying it when we went to the store to pick up a few necessaries. I was carrying it when we went to the house where she was taking care of her friends' dogs and where I had to pick a dozen or so ticks off of the dogs with a pair of nail clippers (worked well, btw, I might add). I wore it all the way up to where we camped. It wasn't untill we had made camp and had gotten settled in and I decided it was ok to take the gun off my belt that she knew I was carrying. She asked to see it. Asked what it was, how it worked, was a little taken aback when she realized that I carried it in the cocked and locked condition but when I showed her how the safties worked, she seemed to take to it. I obliged all her questions and curioisities. Showed her how to clear the chamber and render it 'safe'. Said she hadn't handled an auto pistol before. She grew up in a ranching and farming community and had thus been exposed to firearms early on.
All in all, she wasn't freaked out all that much when she learned I carried a pistol. I told her that her and I hanging out and being together would mean that in many or most places where it is legal for me to carry a gun with my handgun license, I would be and that she would have to be ok with that.
Try this.. when you're out somewhere and you get carded, say at the door or at the bar, hand the bar keep or doorman your CHL instead of your DL as if by accident. Most bartenders and doormen aren'y used to seeing CHL's as ID so he or she will hesitate at it, at which point you step in and say "Oh, did I not give you my driver's license? Here it is. Sorry 'bout that"
If she's paying attention, and if she's interested, she'll ask questions about it "what's that? what kind of license did you give him? Oh, it's a concealed handgun license... Are you carrying now?"
"Oh, well, that's not really a question that's good to give the answer to other than to say that it's not legal to carry in here and I'd like to keep my license.
You'll know right then and there whether she's "down with the cause"
good luck and happy hunting!!
Oh and as a final note, she asked if we could go shooting sometime. I think she likes my 'pistol'