Basically it's been a while since I went on a "first date" with a girl.

Usually all my past relationships we would meet through friends then just get to know each other across different parties we would attend, then finally we would hangout together at her place or mine and it would start that way.

NOW however, i've been talking with this girl for a while and she's completely out of my circle of friends, doesn't live or go out in the same town so we never bump into each other.

Wednesday we're going to get drinks together, and though it'll feel awkward/stressful at first, i'm sure it'll go well.

The question I have is: Do I try to kiss her on the "first date"?

I don't just want to get with this girl once, I find her pretty cool so i'd be down for something more serious. So I don't want to give out the wrong vibe.

Would making her work for it (the kiss) be good?

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My father once told me:"Son, we are good men in the family and don't have much weakness', but you'll quickly learn that women are our Achilles' heel."

You're not giving a lot of detail. Just from your tone...and the amount you seem to be worried about this kiss that may or may not happen you need to examine your frame and approach.