Newbie - FAQ
I prefer that I receive my donation as soon as possible, so I don't have to concern myself with it the rest of the evening. For the love of all that is good and holy, please don't make me ask for it. 
On my dinner dates, I try to meet the gentleman in his room (or at his home) first so we can conduct the "business" aspect there. That's not always possible though, and some ladies prefer to meet in public first.
When giving her the donation in public, it will need to be discreet. Bury it in a gift bag or place it in a gift box (personally, I prefer not receiving a greeting card bulging with cash). What, is the maitre d' going to storm up to the table and accuse you of patronizing a prostitute? Hell no! He'll assume she's your wife or fiancee or new girlfriend you're trying to impress, or just a hot young thing you were lucky enough to take to dinner.
I prefer that I receive my donation as soon as possible, so I don't have to concern myself with it the rest of the evening. For the love of all that is good and holy, please don't make me ask for it. On my dinner dates, I try to meet the gentleman in his room (or at his home) first so we can conduct the "business" aspect there. That's not always possible though, and some ladies prefer to meet in public first.
When giving her the donation in public, it will need to be discreet. Bury it in a gift bag or place it in a gift box (personally, I prefer not receiving a greeting card bulging with cash). What, is the maitre d' going to storm up to the table and accuse you of patronizing a prostitute? Hell no! He'll assume she's your wife or fiancee or new girlfriend you're trying to impress, or just a hot young thing you were lucky enough to take to dinner.
I've only been on one dinner date (BTW - with one of the ladies who have posted in this thread ).
Have the correct amount on you at all times, IN AN DISCRETE ENVELOPE. When I say on you, I mean in an inside jacket pocket, a trouser back pocket, etc. Keeping it in your shirt pocket may be a bit obvious, and you definitely don't want to open your briefcase. Just let her know that you have it accessible, and let her suggest the time to transfer.