Well, I'm no longer single, but when I was....
I would ankle carry until I chose to bring up the subject, so I wouldn't be put on the spot if I was "made." It's easy for a guy to feel up my gun if he puts his arm around me.
And I wanted do my best to control how and when I discussed the CCW thing - I had a better chance of things going "my way."
Usually subjects like favorite hobbies come up on first dates, so I'd mention guns. I would say I have firearms for sport, hunting and defense, but I'd leave out the part about me actually carrying a gun on me, mainly not to spook the other person, and for personal safety reasons. I'd get a bearing on how the other person feels about guns before I went any further. If he was receptive, or better yet, a gunnie, and I felt like we were "clicking," then I'd tell him more as the dating continued.
If the person was against me carrying, well.... that was a sign to move on. At least I'd find out before I fell head over heels with a schmuck.