You must be sticking to some rules when you happened to be stuck in the middle of sticky money situations, such as reacting or handling the "do I" or "don't I" moments about who pays what and when.
Rule no. 1; - you should only pay what you owe when eating with a group. Be sure there is an agreement about what to pay, and who will pay.
Scenario 1: Your friend ordered a steak and a glass of wine, and a dessert. You ordered salad. When the bill comes, she says "let's just split it." How would you react?
Firmly but nicely, you should say "I think it would be best if each of us would pay for what we ordered." Splitting would be okay if the difference is just few dollars, but not for a large discrepancy.
If your friend pushes the issue, stick to your guns and pay for your meal only.
Rule no. 2; Whoever asks, pays. Let's face it. Most of us want the guy to pay on a first date. Then, after that, be happy to pick up the tab once in a while. If both of you are capable adults earning salaries, why should the guy be always the one to pay? The only exception to the rule is that;- if you decide to go out after meeting online, consider it a mutual invitation and expect to go dutch.
Rule no. 3; If you break it, you buy it! This old mantra is commonly practiced in stores, and same thing applies to it if you damage something in a friend's home. The only exception is, if the owner was negligent. Like for example you spilled a wine on her rug because you tripped over a power cord strung across the room. Immediately offer to pay the cost of fixing the item or get a replacement. If you can't afford it, contribute what you can or suggest a payment plan.
If you are the host in your own home and somebody spilled wine on your expensive rug and your friend doesn't offer to make ammends, see first if your homeowner's insurance covers the damage. If not, and you expect her to pay for the item and you feel uncomfortable enough to ask her in person, send her a note saying how much it will cost to replace the damaged item, and ask her if she could contribute toward it. It may hurt your friendship, so think about how much the replacement really means to you.
Rule no. 4; Pay your share. Like for example you bought a birthday gift for your mom, and your sister confesses that she is giftless, and you agreed to go halfsies. Weeks later, she still hasn't given you any dime. If you are more financially stable than your sister, accept whatever she can give and hope she'll return the favor in the future. Otherwise, tell her to make other plans when she first asks to go in on the gift with you.
Rule no. 5; In your work place, there seems to be somebody collecting cash for someone's wedding shower, baby shower, birthday party or retirement bash. Are you required to contribute? In a workplace without politics, no. But on the other hand, you might think your boss would think of you that doesn't belong to the team when you don't give. Look at the situation pragmatically. If the requests are happening too often and for too much money, consider telling your supervisor "Can we rethink this policy?" Then be sure you can suggest some alternatives like putting a price cap on office parties or celebrating only certain events. Who knows? Your boss maybe just as tired of getting hit up for contributions as well.