I think an early evening drink is always good. If it's going really well, you can always extend it to a less formal dinner.
Right on the money dude. As for paying for dinner, I like to pay - it always seemed like the right thing to do. But if she doesn't even offer to split... well, that was sort of a warning signal to me. Actually, maybe it's old fashioned, but unless it is a group, I always found going dutch sort of cheap. With male friends, if it's coffee, we'll take turns reciprocating. With female friends, the same also applies to dinners. "This time it's me, right? Aha. That's why you ordered the lobster." And if it's a group, unless it is very obvious that one person is in dire straits and/or ordered very little because they had eaten already or weren't drinking much, but just enjoying the company, my friends and I will generally just split the bill equally between all parties. After all, what how do you divide up shared appetizers, bottles of wine, etc...? In my parents generation, one person will pay the whole dinner (of course, not every night). Actually, there is a sort of formulistic play at the end of dinner when all the senior men stand up and reach into their wallets and jostle to see the check (always put discreetly near the middle of the table at Chinese restaurants), and their wives chide each other saying that their husbands never get to pay, and that this time it is our treat because we are visiting/we are the hosts/we invited you, etc... Very humorous. And very Chinese.