It's understandable that in this day and age, men would be confused about third date etiquette. After all, what is expected since that whole pesky "women's lib" thing came down the pike is much more debatable. Not every woman agrees on this stuff anymore.
- This is the last date you are required to pay for in its entirety. Now, the operative word here is "required." If you really, really like this girl, you should continue to pay her way beyond the third date if you can afford to, especially if you know you're worth more than she is. Having said that, it would not breach third date etiquette for you to ask her about possibly going dutch or paying for the cab fare on the fourth date; just know the risk that you take. You absolutely must pay for everything on the first three dates to avoid breaching etiquette. Dinner, cab fare, movie tickets; all of it. It's up to you to choose meals and activities you can afford.
- You can deepen the conversation, but don't go nuts. Having passed the first two dates with flying colors, you can now feel free to drop the "I'm on my best behavior" facade without breaching etiquette. That is not carte blanche to spill absolutely everything, i.e. you can tell her you're in therapy, but don't necessarily go into vast details as to why just yet. If she presses you, you have every right to say you're not comfortable discussing seriously intimate details so soon. You can drop a swear word or two into the conversation and see how she reacts, but don't pull a total George Carlin on her yet. If she bolts because you're not perfect, she wasn't worth your time anyway.
- The Third Date Rule. Okay, here's the part you really wanted to know. Yes, it is appropriate to discuss sex at this point but you should only do so before this point if the discussion is initiated by her. No, it is not appropriate to expect sex at this point. Simple enough for you gentlemen to understand? The Third Date Rule is not the silly catch-all it was once thought to be, and we should be past this by now. Just because she declines sex on the third date doesn't mean she always will or that she's waiting for marriage; women are individuals and some just want to wait longer.
- It's still too soon to be jealous. Third date etiquette allows for talks of exclusivity, but you have not yet earned the right to pressure her into it (if she's still hemming and hawing by the fifth date, it's probably time to move on) and you certainly have no right to be jealous of her attachments to other men unless it's really clear she's not over someone in particular, in which case you'd be right to see a warning sign. However, if you're already uncomfortable with her platonic male friends and you even suggest that she cut down her time with them this early in the relationship, she's going to peg you as possessive and run like hell, and rightfully so. Be careful.
- Religion and politics. Don't proselytize, but if these things–or the lack of these things–are important to you, then third date etiquette indicates that you probably want to drop them into conversation now if you haven't done so already. If they're not, they may be important to her so you'll want to at least broach these topics–lightly at first–at this point anyway. Let's face it, these are dealbreakers for a lot of people, and while you don't want to launch into intense discussion of them on the first date, you do want to get it out of the way before you get too invested. Man up and get this done before you touch her; you'll thank us later.