Brent, thanks for kinds words and I'm glad to hear you're enjoying the blog. Your question's a good one, and yeah, tough stuff to figure out exactly sometimes.
"This has happened a few times so I'm just confused. To pay or not to pay? I think it really just depends on the situation?"
This is one of those things where I'd probably say you succeeded in spite of it. Attribution is a killer for that reason... for instance, say you launched into a really long-winded story, and the girl seemed bored, but then you ended up taking her to bed later. Did the story actually help -- or did you bed her in spite of it? It can sometimes be hard in retrospect to figure out what helped and what hurt and what really didn't play much of a factor either way.
There are a few instances in which paying can be okay, and you seem to have found one of them in your example. If you pay for something, and then she pays after, she'll often end up feeling like both of you are investing in the two of you getting together -- which can actually work out quite well. If only you pay and she doesn't though, any women you take to bed following an evening like that I'd be inclined to say you bedded in spite of paying. I've had dates that ended with the girl in bed where I'd tell her I'll pay for the drinks if she'll pay for the food, and such arrangements.
Migz, that's for sure a potentially dangerous trap to avoid. Always good to try and start things off on the right foot, and the earlier something begins in a relationship, the faster it gets cemented as a long-term expectation.
Even if you want to be paying 75% of the time later on in a relationship, it's just good practice to get in the habit of not doing so early on so that she doesn't start taking it for granted that you'll pay.
Great comments here gents, and great discussion. Cheers for that!