All of these questions should be discussed with her. Honestly, if you don't feel comfortable enough to approach her with this stuff I have serious doubts about how much fun you will have when confronted with the prospect of filling a couple of days worth of time together.

You will need to know her real name to buy her a ticket, not for a hotel reservation unless you are staying in separate rooms. Again, you should not be afraid to raise all of these issues with the lady...best of luck.

So you think you know her? You don't and making assumptions is not a way to get started. She's bi? So let her enjoy the room with the hot person she sees on the beach and make yourself invisible for awhile... Have you ever done a double with her? How can you assume the lady she might meet is in the biz or wants to double with you? ATFs are fine but they like any of us need their space and alone time. You sound stifling and at the end of this, she may be your ex-ATF

You should lead up to things like this to see how things go.

For example, start with a four hour dinner date, then if that is fine, proceed to an overnight, then a 24 hour.

Traveling and spending a lot of time intimately with someone reveals cracks that may or may not cause either of you alarm.

Ask her if she wants to get her ticket and reimbursed after.  
With the new 911 laws, when someone purchases a ticket for another who has a different last name, she can expect to go through extra security at the airport.   Been there, not fun.

You should pay her up front for all fees and expenses.  Then, she can place in in a safe place and no more money talk, just fun.

When you're at dinner, tell her your fantasies and ask if she's open minded on what transpires over the holiday.  Ask her if she's ever been on holiday with another gentleman and how that went.  It might give you an idea of her expectations.  Also ask her to go over no-no's to avoid ackward situations.  

Have a great time!

-- Modified on 12/17/2007 11:20:37 AM