And when money is involved, what’s your approach to not make it turns into an endless awkward back and forth because both sides want to pay?
Offer once if they don’t accept that’s it.
That’s how I do it too. Then again, Germans are allegedly very blunt and direct when it comes to such things. My social group certainly is, no shame in offering or accepting. I suppose it’s different in other cultures or social groups.
My rule is ask twice, but the second time being a very simple “are you sure? It’s OK, I’m happy to contribute / half / cover” (delete as appropriate).
In the UK at least there is still a level of “pride”, for want of a better term, with either not accepting charity, or being seen to treat people you care about. There is also an expectation that you should be humble and gracious when receiving a gift so you also should reject it at the first instance. If the offer is only made once then all that is really happening is both sides are playing their parts and nothing else.
The second time is to acknowledge that it was a genuine offer, and not just part of the dance.
If the other person still insists, regardless of what it was, then you accept it. And maybe keep a mental note because next time it would be nice for you to return the favour if they treated you.
Offer to pay, if they decline accept it, but declare “next time it will be definitely my turn” and remember that for next time.
I recommend this too. Some of my friends and I take turns paying for things such that we’ve long forgotten who was first. It makes it so that you always have an excuse to see a friend (“Hey, I owe you a beer!” or “You owe me a beer!”). It’s so easy to get sucked into work and life and such, that it’s sometimes the little push I need to see them, or the excuse I need to get them to come over.
Offer once, if they refuse give a single counter and then if they still decline, accept it.
A: “I got it.”
B: “No, I’ll get it.”
A: “Are you sure? I don’t mind.”
B: “No, I insist.”
A: “Ok”
