The woman shall determine, prior to departure for a trip with a kind gentleman, what her relationship is with him, and her financial commitment to the trip shall reflect that level of interaction.
This one you must look at on a case by case basis, friends.
If you know you and a guy you're traveling with are absolutely friends, be sure to split everything - cabs, bar tabs, hotel (if you're sharing a room), etc. - down the middle. That way, you can feel confident that you're not setting up any false expectations. Not that your guy friend (if he is indeed a genuine friend) would expect anything by covering more than you, but splitting all bills will give you the assurance that at the very least, he shouldn't.
If you and the guy are more than friends, work out with said more-than-friend what the fee structure will be before you make reservations for that Tier 2 hotel. A guy once suggested a trip to me. He said "I wanna take you to {insert desirable resort town}" and he asked me to make reservations...using my credit card.
When I got the guts to ask him how we'd be handling the hotel bill (perhaps two weeks before the trip), he was more wishy-washy than Tide Ultraclean. Needless to say, I canceled the reservations- and my further investment in a relationship with him.
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