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I might be in a minority, but I would honestly say just talk to him. I know that some people are old fashioned with the "who does the asking should do the paying" but in today's day an age, money is always a factor. Maybe just ask if he can "pitch in" some, but not really go "straight dutch". I mean if he wants to pay for half of the hotel, by all means if you feel comfortable, accept it, but if you don't don't.
I'm sorry. I'm not much help am I ?
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"Courage is not the absence of fear, but the capacity to act despite our fears" John McCain
No one can make you feel inferior without your consent." Eleanor Roosevelt
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