Can't really help -- we met online, and had a long-distance relationship with approximately monthly visits for 1 1/2 -- 2 years before moving in together, but never really dated.

Personally I don't think I could manage to talk about D/s stuff with someone I was "dating" in the way I think of that word -- i.e. just getting to know each other. I associate dating with little flutters in the stomach and still trying to present the best side of myself and getting all blushy every time someone gives me a compliment, and also with horrible nerves when he's late to pick me up and trying on 10 different outfits that all make me look fat and being really, really self-conscious about my table manners. I don't think I'd have the nerve to deal with all of that plus telling someone "oh by the way, I really like to be tied up and humiliated. Hope that isn't a problem!"

OTOH, the idea of dating someone who set himself up as in charge from the get-go is actually pretty hot... I'm imagining this person (who is going to be Kyle MacLachlan because this is my post dammit) calling on the phone and saying "I'm going to pick you up at exactly 7:35 PM on Friday. You will be waiting for me in the lobby wearing a red dress, black pumps and no panties." ... sort of takes away some of the anxiety of the situation...