I don't have a CCW yet so I don't carry (gotta wait a few more months till I'm 21, and I'm also in the process of joining the Navy, so I probably won't be able to carry until I live off base), but I plan on always carrying whenever I legally can. And personally I wouldn't date anyone who would have a big problem with my ownership and carrying of firearms.
But I'll tell you this though, I usually take the girl on a date to the shooting range pretty early on. Like second or third date. You'd be surprised how often that breaks the ice on the whole subject, and usually leads to them better understanding the whole gun subject.
For example, I have a friend who is one of these "VERY artsy liberal starbucks coffe drinking tofu eating" types (that's about as well as I can describe it, LOL). I tried dating her a couple of years ago, but it didn't really work out, however, we're still friends to this day, and I actually took her to the range not all that long ago, and she absolutely loved it. She loved it enough that she's even considering getting a gun of her own one day... even though she's a card carrying, NYU loving liberal
... I may not really change her political views too much, but at least I helped change her views on gun ownership. People tend to fear what they know nothing about, so if you teach them, some of that fear goes away, and I've found that alot of people are natrually curious, so it doesn't take that much to get them to come with you for a day at the range.
So yeah, my advice is to bring the subject up as something fun (like taking her out to the range one day), and go from there. I find that this works pretty well for women, especially if you take the time to talk to them about safety, responsibility, and stuff like that... they usually like that alot.
Well... that's my view on that.