How else were you thinking of paying her?
I've been seeing a provider for a couple of years and I'm thinking about asking her to accompany me on a vacation later this year. Just wanted some suggestions on the best way to handle the method of payment?
How else were you thinking of paying her?
How about you ask the provider in question? If she's done it before, then she'll have a clear answer for you. If not, then talk out what's comfortable for both of you. Some may want the payment in full before she gets on the plane, some will accept it at the end of the trip before you part, some may do half now/half later (or some variation of deposit now, in-full later).
Do expect to pick up the full tab of expenses while you are on the trip.
The provider!
There really is no "right" way to handle this, so it would be wise to just ask her directly. Every provider has her own way of arranging travel (if they're even interested), so all the advice in the world isn't really going to help you out. If you can't find the information you need on her website, it's a much better idea to simply ask HER what she wants than to come to her with a plan of how YOU think payment should be handled.
Since it sounds like you two have a great relationship, you could probably ask her just like you asked us: "Hey, I'd really love for you to accompany me on a trip. Is that something you're interested in? How can we make that happen?" I'm sure she'll appreciate it 
And it's pretty easy to figure out too!
Steph
The OP is considerably more interesting than you might think at first glance - unless of course, your name is Guido and you commonly handle your money in paper sacks.... but many of us are legit people who handle our financial affairs using the banking system...
So - you negotiate with a hooker for a nice trip to where ever for how ever long for 20k - just to pick a number. And she suggests cash (as hookers do...)
It's one thing to go down to your local BofA and cash a check for a couple of grand - put the benjis in envelopes and go distribute it to deserving young women with financial needs. Sort of like Santa Claus...
But 20K seems like a lot to handle in one transaction - and very tedious to handle in multiple transactions. If you don't watch out, you are going to attract some attention from some very unpleasant folk working for our even more unpleasant government who might think you are, for example, avoiding the payment of payroll taxes. They REALLY don't like stuff like that...
And - I don't think an envelope is really going to handle it.... And a briefcase is too big - Maybe a sack? Guido would be proud...
So - all that said - what ideas do you have? I have no idea what the solution would be - just some ideas about what the problem looks like...
-- Modified on 7/30/2015 6:28:19 PM
Twenty grand in hundreds fits quite comfortably in two of those little bank envelopes. Back in my casino days I used to refer to ten grand as "one envelope"
I would strongly advise AGAINST pulling the cash out in small increments. "Structuring" is a lot more serious problem than simply pulling twenty grand or so out of your account in one transaction. If ever asked by the IRS, you can always say it was for gambling or some other legitimate personal use. Trust me, you don't want to give the impression that you are trying to hide the transaction/s, I trust whatever the amount is, it is not anything more than a small percentage of the OP ready cash reserves, and shouldn't raise any eyebrows. If it is a HUGE transaction by "his" standards, than maybe he is spending more than he should be on this little trip, but nothing the OP has said would give anyone cause to think this is more money than he can afford.
Once again, I really don't see an issue here. Go to the bank, get the cash, pay your hooker and have a GREAT time. Why the angst?
Thanks for the tip! I really had no idea that my local branch kept enough cash on hand to just give me 20k at the teller window. Sheltered life I guess...
...on the corner mailbox. When I hide the package in the nearby bushes, I will cross her line, making an "X." She will see that the drop was completed and retrieve the package.