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Tough question. The thing is, your new potential g/f could be one of four major groups: pro-gun and pro-OC, pro-gun but anti-OC, anti-gun but convinceable otherwise, and totally, unconvinceably anti-gun. If she's pro-OC, home run. If she's totally and rabidly anti, the date's over as soon as she finds out you're a gun person and there's little you're going to do to change that.
But, most people are somewhere in between; they either like guns butregard OC as "the cowboy macho look", or they don't like guns but only because they have no firsthand experience with them and get their opinions from political pundits. You stand a good chance of changing the mind of a girlfriend who falls in either of these two groups. However, you will probably set yourself back quite a bit by being openly and forcefully pro-gun (in their mind) by OCing.
It all boils down to whether you want to bother trying to change your g/f's mind, or just say goodbye after the first date if she's not as pro-gun as you,and try your luck with the next girl. If you want to give talking a try, I'd conceal the gun if you can legally do so or leave it in the car if you cannot,bring up guns as an interest duringan opportune moment, gauge her reaction, and work from there.Personally, I'd go this route; Ihave not yet met someone who didn't at least understand the need for an average Joe to have a handgun, and even though the majority of people I've discussed the matter with have been somewhat skittish, they're generally open to the idea ofhaving atarget shooting pistol if not a carry/home defense weapon.
If you don't want tohave to change a potential g/f's mind about guns, just OC. You'll quickly weed out the antis, that's for sure. Trouble is, you never get a second chance to make a first impression, and even if your g/f has a concealed carry permit, a gun on the hip of someone you've never met can be unsettling. A girl may not need any convincing; just time to adjust to the sight of guns being around. Meeting you with a gun on your hip gives her approximately zero time to adjust, so you will probably weed out all but the most pro-gun girls before the first hello.