Too often I've been out with friends and one determines they should pay for the group. However, I've never actually done so. This usually happens when I'm out for a drink with one friend.
When should I offer to pick up the tab or check? How can I tell if someone else plans on picking up the check? If they offer, should I counter offer?
Great question! A lot of this depends on the particular situation. If, for instance, you're a junior on a job and a senior worker (and friend) suggests that you go out for a Pepsi together, if he offers to pay, an "Oh, thanks!" is all that's necessary.
On the other hand, if this among friends whom you frequently spend time with, I personally just try to take on my fair share of it. In other words, if we go out, say, once a week with four of us, I'd just take the tab once every 3-4 weeks.
Furthermore, it depends on the value you put on the given relationship(s). If these are good friends, for myself, I'd offer to take it just a bit more often than what would be my "fair share."
As to telling if someone else is planning on picking it up - it really depends on the situation again. If you know the friends well, it's not too bad, but if they're people you don't really know all that well, it could be a bit more tricky.
To a large extent, it will depend on your particular area and circle of friends. I'd recommend taking the trouble to observe who usually suggests going out and who usually picks up the tab. Is there some observable pattern? Is it usually the person who proposes it that ends up paying? To a large extent, you can avoid doing something embarrassing simply by observing and doing like other people do.*
*This is a general rule that does not apply in all situations. Use your good sense. :)
Ultimately the "considerate" thing to do is what the other person wants you to do. So you should "offer" to pay, and if "overridden, let the other person pay.
One thing you can do with someone who is paying is say, "I'll get that the next time." That way, you fulfill the social contract while letting the other person pay this time.
As with anything, it depends on a lot of things. One things that wasn't mentioned yet in the answers at the moment of my posting, is that sometimes you order considerably more/less expensive food and drinks than others, and it would be unfair to severely overpay or underpay your share of the combined tab. In cases like that you might want to just explain the situation to your friends:
Hey, I've noticed that I'm not ordering nearly as much as you guys, so I think it's only fair if I only pay for my share (this time).
Or, if you're feeling generous, just split the combined tab evenly between the N of you.
It's not too uncommon to have one friend in the group who often wants to try expensive items from the menu, and to have them pay for those from their own pocket, without burdening the rest of the group with their whimsical expenses. There's usually an understanding that it's the reasonable thing to do. And if there's not, you might bring that up with them at the next gathering and explain the situation from your point of view.
