Befriend for Benefits?
Question: I have an ethical/moral question. I recently met someone while out who was laying it on pretty thick, flirtation-wise. I am not attracted to him but he’s funny and well-connected–connections which could, perhaps, benefit me one day if we became friends.
Can I hang out with him (even though he will probably assume it might lead to something) or is that entirely too enterprising and shitty?
Answers: How much potential manhandling are you willing to circumvent? But that's not your question...
Since you present this as a moral conundrum, my vote is that it's fine to befriend this person under one condition: You like his character. You find him funny, but do you actually like hanging out with him?
If you think he'll be an enjoyable acquaintance to have, then don't let assumptions hold you back. We're friends with people because they add to our lives, making our worlds feel larger. This is no different, so long as you recognize that it'll be on you to dispel any false hopes he might have.
However, if he's someone you wouldn't give the time of day were he less well connected, then yes—hanging out with him would be enterprising and shitty. Plus, any time you'd spend with him would be a literal chore, unlikely to yield any lasting benefits. Kind of like dusting.