I tend not to get "romantic" with women that I haven't gotten to know well enough to tell how they might react to such things. Politics is a passion of mine and if a girl doesn't have an opinion along with the ability to discuss it rationally, well, she'd better be REAL darn good looking!
I've gone on first dates with a Glock 20 concealed discreetly under my clothing. At 6'7", there's enough room to hide such things. It never flashed, and by the time it may have become an issue that evening, she was too distracted to notice.
The most I've ever gotten was:
Q. "Why do you need to carry a gun?"
A. "Because I love people."
That answer tends to short circuit the soccer mom reflex.
Either they trust you or they don't. Any girl who would cut contact with you over gun ownership isn't someone you want to spend the rest of your life with, anyway.
The current SO says that until she met me, she thought only insane lunatics or cops carried guns around. My response:
"How did meeting me change your opinion?"