I am sure most would. However, the question is probably the other way around. Do you want to do an overnight with someone that you have not done a couple of hours with first? Most of the wisdom around generally tends to be try the person out and then if you have felt that an overnight would be appropriate, go for it. An escort will expect payment if you have made an overnight appointment if you decide to leave because you just don't "click." He could have (or might have) booked other people. So my advice is to try him out for an evening and then if you really like him book him for the next night if you really have to have him or another trip if you are leaving right away. But that is just my advice.