Also....
I don't know what your funds are like, but since we *are* in Diamonds and Tuxedos, I'll assume you belong and say this:
If you aren't trying to spend thousands, find a provider that you absolutely want to see, either fly her to you, or fly to her. If you live in a metropolitan area, ask your HDH if she would like to tour your city, and if so - offer her a round trip ticket here (say for a week) and negotiate the rest. A dinner package with a HDH (play time M&G, dinner, entertainment, XXX dessert) runs $650 - $2000 depending on who you are seeing and where. Offer traveling concessions in exchange for a dinner date or something. Round trip airfare and the hotel paid for for the week - you get a session, and she gets a week of free touring to generate business in a new city.
Originally Posted by TravelingGentleman
Barter is always a tricky situation. Not that it shouldn't be done and there are, like always, varying valid opinions and levels of comfort with barter. I'm not a fan for a number for reasons I certainly would not recommend it for a first date. Too many moving parts.
If air travel is involved it requires her revealing her real world id to you to book her travel. On your end, you open yourself up to exposure having a hotel room rented to you that she uses for the balance of the week to conduct business. In the event something happens it's your room. We all take risks in this game but I don't like taking risks when I'm not there to control the situation. As an aside, if I see a lady for a date and get a room & she asks if she can stay after I leave to "sleep" or "rest up" I always decline. I recommend having a grown up conversation with her & if she wants to "work" after our date she can reserve the hotel room and we build that expense into the price of the date.
Remember in the HDH world these are not BP gals that need you to front them cash so they can get a room at a motel 6. They are adept at making their own travel arrangements.
Really the only reason barter makes economic sense is when your have a (access to) good or service that cost you less than fair market value or a price the other party you reasonably pay. In the case of air travel or lodging, points or miles, particularly when you got millions of them, can be tempting but I wouldn't do it on the room under any circumstances for my protection and I think she'd be leery of a new client/friend offering to fly her in....it just makes for an awkward initial approach.