1. Your friend wants to borrow money, but she never paid you back for the last time you lent her money. What should you do?
The Answer: Whenever you offer money to someone, it's best to consider it a gift rather than a loan, and accept the fact that you may never see it again. However, if you're simply not comfortable lending out money, be honest -– explain that you need to prioritize your own finances -- whether it's paying your bills or saving for a personal fund. Remember that it’s okay to say "no."
2. How do you deal with a nosy relative who likes to ask how much you spent on your house, car, or recent vacation?
The Answer: Recognize that you're not in any way obligated to answer even at the risk of seeming impolite -- it's impolite to ask in the first place! A way to deflect their line of questioning is to respond with something along the lines of, "More than I should have, honestly." Then, immediately change the subject. It lets the person know that the topic is not open for discussion without embarrassing them.
3. Who do you tip and how much?
The Answer: It depends! Of course, we know it's customary to tip waiters and hotel staff. But what about everyone else? Here is a good rule of thumb: only tip the people who provide a regular high level of service. Depending on how often you employ their services, this could be a doorman, building handyman, mail carrier, or a dog walker.
4. You had soup and salad. Everyone else had a steak. How do you split the bill?
The Answer: First, consider the difference in the numbers. If there is only a few dollars’ worth of difference, it's best to split the bill evenly. If there is a significant difference –- and frankly, one you can't afford -– it's best to pipe up and say something like, "I think $40 ought to cover my meal and tip, right?" Then let the rest of your party split the bill as they see fit.
5. A family member or friend always assumes you will be the one to pay. Is there anything you can do?
The Answer: When planning your next outing, you can mention the implied finances in a friendly way. Say something along the lines of, "A trip to the museum would cost about $25 each. Want to go together?" This makes it clear that the cost is divided evenly between you -- leaving your half of the tab covered, and leaving her to cover her half.
6. Your friend is going through a financial rough patch. Is it appropriate to offer money?
The Answer: As a sincere offer, yes! It also doesn't have to be a lump sum. When you're out on a lunch date and the bill comes, say something like, "Please let me take care of this today. I'm just happy to share the time with you." But do not make this a regular situation -- a dynamic like that will make your friend feel uncomfortable. Even better, if you know that your friend is going through financial troubles, be considerate of her situation by offering activities that do not require spending money. Instead of inviting her to an expensive steak dinner, invite her to a make-your-own pizza party.
7. You'd like to solicit the advice of an acquaintance who happens to be an interior designer, accountant, or gardener. Should you pay him?
The Answer: It's simple: yes. Just because you have a personal relationship, doesn't mean that you should assume his professional expertise will come for free. In fact, it's better for your relationship if you quickly offer compensation for his time and advice.
8. You always host the family for holidays, but no one offers to help and it's getting expensive. What can you do?
The Answer: If you're the go-to entertainer for the family, it's easy to feel burned out. This year, tweak the tradition and suggest a potluck. This helps trim down on your costs and helps everyone feel more involved. Want more etiquette tips to holiday entertaining? Watch Martha's suggestions in this video: