Your first date went well and she appeared to have a good time. For starters you went to see the "Buena Vista Social Club," which she really enjoyed because it featured Latin American music and you could see she was ready to get up and dance during some scenes.
From there you walked a few blocks to the "Brooklyn Chop House," and this is were things were going to get interesting.
Now, most women if they are smart will let you hear them think out loud. What do I mean by this? Women will see an expense item on the menu and will mention how that probably looks good, but it's too expense (she may have really had her heart set on getting 48oz Dry Aged Porterhouse Steak@ $189.00, but will say that it cost too much and tell you that she's order the Sweet and Sour Chicken@ $32.00 and some French Fries@ $12).
You're trying to impress her and keep her happy so you end up telling her:
"Don't worry about it get what you want"
Her: "You sure?"
You: "Yes"
Her: "I can help you with the bill"
You: "I'll be okay, get it"
17 - 22 year old you would probably be taking her to "Ray's Pizza Shop" to get 2 slices and some sodas.
She'll order what she wants, but she was smart enough to mention the cost of the items and that she was willing to help you when the check comes, in addition, she'll even offer to pay the tip.
Do yourself a favor and don't bother doing the math on what you've paid so far and just enjoy the moment. Furthermore, irrespective of how much you spent already don't tell yourself that she is obligated to let you "hit it."
Nevertheless, you make sure she gets home safely and she invites you in and...