Why or why not?

For the sake of question, assume that the place in question is within the budget range where you'd go by yourself, or with friends.

Questions to consider:

If you offer to pay for yourself, how genuine is the offer? Is he expected to refuse? Will accepting your offer make him less desirable in your eyes?

If you don't offer, then how do you deal with the bill? Do you just count on them offering to pay for you?

If they offer to pay for you, will you accept immediately or would you insist on paying for yourself?

Would you ever offer to pay for them?

Does your response depend on whether you'd like to see him again?