Reminds me of an incident that happened on Thursday. I had to take my GD to get fingerprints redone for her nursing license. There was a guy in there, who was re-applying for his CHL. We started talking, and I asked him where he went to shoot and found out that he frequents the same place DH and I shoot. Well, another guy came in and heard the last part of our discussion and said that he wanted to get his CHL. After the CHL holder left, the new guy asks me what I'm carrying. BIG red flag!
I just smiled at him and said, "There are two things that a gentleman would never ask a lady: her age and her carry status." 
Well, he was not to be deterred, and he kept on trying to find out, but I just turned the topic to what guns he had ... and there were many, if he was to be believed. I don't tell strangers, but I'm on a mission to get as many women armed and in control of their destiny as I possibly can.
Given the fact that women are twice as likely as men to be attacked and comprise such a tiny number of CHL holders, it's a big job, but the pond is FULL of fish! So, far there are two converts from my church and several more from my political women's organization. In just a couple of months, that's something! We all have found out that punching holes in paper targets with bullets is a hoot!!! 
So, tell or don't tell? My answer is an unequivocal ... sometimes.