From gift-giving to check-splitting, here's how to take the stress and confusion out of money etiquette.
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Money etiquette is a confusing blur of gray areas and a lot of "it depends" moments. The economic climate is also constantly changing and many people are experiencing heightened financial stressors that could put even more strain on money-related social situations. Any time you find yourself up against one of these potentially confusing or awkward scenarios, follow the tips below from money and etiquette experts to ease the discomfort of talking it out—whether you're asking a coworker to pay you back, or trying not to get stuck splitting a giant group dinner bill.

1 How to Handle Venmo Transactions

Scenario: You're at a group dinner and someone put their card down for the bill, or one friend bought multiple tickets for a show, or someone called an Uber ride for your whole crew. What's the protocol for getting squared away?

Response: No matter the scenario, if someone else Venmo requests you for your portion of an expense, you should complete the requests right away. "If someone was helpful enough to put that big tab on their credit card, they should be reimbursed ASAP," says Colleen McCreary, Credit Karma's financial advocate and chief people officer. "Imagine if you were the one fronting the bill—you would want the peace of mind that the money is back in your account as quickly as possible."

And in the scenario in which you are the one to pay for a group cost, McCreary recommends taking the initiative to send out Venmo requests right away, instead of waiting for people to send them to you. "Tell your friends that you're sending out charges, and that you'd appreciate it if they could complete the charge by the end of the night so you can transfer that money to your bank account right away," she says. "Absorbing multiple bills can lead to you losing track of money you are spending for others and by sending out charges right away, you ensure you're paid back in full." This also sets a precedent in your friend group that when someone pays for everyone else, they can be expected to be reimbursed quickly.

2 How to Handle Splitting the Bill at Group Dinners

Scenario: The check arrives, and while you had a salad and one glass of wine, everyone else had steak and three cocktails.

Response: If there's only a few dollars difference, consider splitting the bill evenly. If you're really in a money crunch―or the house wine you had doesn't exactly compare with the three $100 bottles the rest of the group shared―say up front, "We're all paying for our own meals and drinks, right?" Make it plain and simple. If it's a large group, you can also ask your server for a separate check when you order. Most restaurants have software systems that can easily print multiple checks. If you don't get a separate check and one of the pricey wine drinkers moves to split the bill evenly, it's OK to be pleasantly honest, says etiquette expert Anna Post, author of Emily Post's Wedding Parties ($10.32, amazon.com): "Try, 'Hey, guys, I figure $30 will cover my meal, glass of wine, tax, and tip. Do you mind if I throw that in and let you split the rest?'" Your message is clear ("I owe less"), but it's not confrontational.

Another tip for avoiding the awkward splitting-of-the-bill discussion is to make sure you're comfortable with the price range of the restaurant before you get there. If you're the friend suggesting a restaurant, check in and make sure everyone is comfortable with the prices. If another friend is making the plans and you don't think you can afford a certain spot, don't be afraid to make a more affordable suggestion or let your friends know ahead of time that you'll have to order something small to make the outing fit your budget. 

3 Tactful Ways to Solicit Donations

Scenario: You're passionate about raising money for several charities. How many times can you hit up the same people?

Response: You can approach immediate family for pretty much every fundraiser you support, from cookie sales to charity races. However, if you solicit distant relatives more than twice a year, email them annually and ask which causes interest them most, suggests Allison Blanton, the senior development adviser of Susan G. Komen for the Cure. "That way, you don't inundate them with requests unless they've said it's OK," she says. With friends and acquaintances, limit yourself to two or three requests a year. Group emails (with recipients' addresses hidden, to protect privacy) asking for contributions are fine. It's always a good idea to send a thank-you note or email when a fundraising project is over, to communicate your gratitude and to let donors know their generosity made an impact. But remember: You'll get better results―and keep more friends―by targeting your solicitations, rather than blasting your entire address book. "If it's the symphony, contact friends you know are passionate about the arts," suggests Caroline Tiger, author of How to Behave: A Guide to Modern Manners for the Socially Challenged ($12.95, amazon.com). "And save the call to pet-loving friends until you're raising money for the animal shelter."

Another important aspect of soliciting donations, wealth manager and behavioral finance expert Shari Greco Reiches says, is making your own donation to that organization and strongly believing in the cause that you're asking others to support. Don't just hop on a trend of asking people to donate money somewhere—be ready to share bullet points on the impact of the organization and why you personally believe in it.

4 How to Handle Friends With Stressful Spending Habits

Scenario: You have a friend who is constantly worrying about money, but appears to be doing a lot more spending than saving. 

Response: Just let it be. "You spend your money the way you want, so let other people do the same," McCreary says. "How we spend our money is personal. If someone seems to be spending their money in a way you don't approve of, that shouldn't be your concern. Judging people on how they spend their money isn't productive, so shift your focus to your own spending and saving habits."

If you're truly concerned that a loved one may be struggling financially, you can assess whether or not you'd like to offer a helping hand or check in to see if they're doing OK. But if you're judgment is just that—judgment without empathy—it's better to stay focused on your own finances.

5 How to Lend Money to Friend or Family Member (Without Awkwardness)

Scenario: Your friend or family member needs some help with an expensive bill or a family member needs a cosigner for a loan. What should you do?

Response: It is natural to want to loan money to loved ones in need, but it's important to evaluate your own financial ability first. "If loaning money is going to put you in a bad financial situation, make sure to explain that you would like to help but cannot contribute financially at this time, and see if you can assist in another way," Rod Griffin, senior director of consumer education at Experian, says. "If you do choose to loan out money, make sure it is an amount that you are comfortable giving, and clarify expectations for repayment."

Or, instead of establishing a repayment plan for the loan, "you're better off making it a gift and not expecting it back," says Dave Ramsey, author of The Total Money Makeover: A Proven Plan for Financial Fitness ($27.20, amazon.com). "That's much less awkward." 

If you're asked to cosign on a loan or be a joint account holder for a credit card, Griffin says to proceed with lots of caution. "When you cosign a loan or add someone as a joint account holder on a credit card, you are agreeing to pay the loan amount or charges if they don't," he says. "That means you are legally responsible for the entire loan amount or charges they make. The loan or credit card will appear on your credit report as well as theirs, and any late payments will hurt both of your credit scores. Declining to cosign might hurt feelings for a bit, but having them wreck your credit history and financial standing can permanently damage a relationship."

RELATED: 9 Tips for Lending Money to Family Members Without Any Awkwardness or Stress

6 How to Know if You Should Pay Friends for Their Professional Advice

Scenario: An acquaintance is an interior designer―or an accountant, an attorney, or another type of professional―and you want their expert opinion. Should you pay them?

Response: You should. "Many people seem to think their friends and acquaintances go into particular professions because, all money aside, they just love their work," says Nancy Barsotti, an interior designer in New York City and Pittsburgh. "They assume that justifies asking for free help." It doesn't. Definitely plan to pay for your friend's professional time and advice, even if they're enthusiastic about their job. "If they don't bring it up first, say, 'How are we going to take care of the business side of this? Will you draw up a contract that outlines what you'll do and how much you'll charge?'" Barsotti suggests. That way, you won't be surprised when the bill comes. If your pal offers a little decorating advice, helps with your taxes, or draws up a will for you for free, a gracious way to show your thanks is with a gift certificate to their favorite restaurant or an invitation to your house for dinner.

7 How to Contribute What You Can to Group Gifts

Scenario: Some of your other friends want to get an expensive group gift for someone's birthday, and it's way more than you want to spend. Should you speak up or just go in on it with them?

Response: If someone's already purchased the lavish gift and is announcing what each person owes, you can "thank the person for making such a nice choice but tell them, 'We already had another gift in mind, so we won't be able to contribute,'" suggests Robyn Spizman, author of The Giftionary: An A-Z Reference Guide for Solving Your Gift-Giving Dilemmas...Forever! ($5, amazon.com). "Then go buy something in your own price range." The other option: If the present is still being decided upon and you'd like to make the case for something more modest, send a friendly group message. Make a specific suggestion, such as a gift certificate to the their favorite restaurant with a suggested per-person contribution. If they all agree, offer to pick up the gift yourself.

8 Tips for Backing Out of a Financial Commitment

Scenario: You committed to a weekend with friends, but the cost is over your budget.

Response: Any time you're going to split the cost of something with friends, be clear about expectations from the outset: "I can afford economy airline seats but not first class." Or, "Can we agree to keep the room under $100 per person per night?" suggests Charles Purdy, author of Urban Etiquette: Marvelous Manners for the Modern Metropolis ($5, amazon.com). If a friend makes expensive reservations before you've discussed it, be upfront. Say, "I misunderstood how much you were planning to spend. I can't afford a trip like that right now." If you agreed initially and are backing out, you could offer to pay a portion of the cost, such as the room-cancellation fee. "That's cheaper than paying for an entire trip you can't afford," says Purdy. But what if your friend says they'll lend you the money and you can pay her later? "Don't do it," says Dickinson. "That's how ex-friends end up confronting each other."

9 How to Collect for Group Gifts Without Coming Off as Aggressive

Scenario: Friends or coworkers who need to reimburse you for a group gift keep saying, "Yeah, I'll get that to you," and never do. What should you do?

Response: Send an email reminding everyone you're collecting and would appreciate it if they'd get their share to you by a specific date, suggests Susan Hackley, the managing director of the Program on Negotiation at Harvard Law School. "If people still haven't paid within a week, another pleasant email―appreciatively noting the names of those who have paid―is perfectly appropriate," Hackley says. If only one or two people haven't chipped in yet, talk to them privately, says Spizman. "Ask if they sent it and by chance you didn't receive it―don't be accusatory. They really might have forgotten." It's also possible they're short on money. In that case, you could compromise and say you'd be willing to accept whatever they can manage. If this puts you in a bind, you might ask some other group members (without revealing intimate details) if they'd consider chipping in a few extra bucks, since the group ran short.

10 How to Talk With Family About the Future

Scenario: You need to start thinking about estate planning and financial plans for the future, but it feels scary and uncomfortable to discuss. Where should you start?

Response: As Meg Palazzolo, head of member success at Trust & Will, says that many of us are conditioned to keep financial matters private and think of money talk as taboo. "But data suggests this is a losing strategy," she says. "More than 70 percent of families lose their wealth by the second generation, and 90 percent of it by the third. The primary contributing factor is that families generally don't discuss money topics with each other."

The solution, then, is to actually talk these things out. "Take advantage of quality, in-person time to talk to your family about your plans for the future," Jonathan Abelmann, cofounder and president of digital life insurance company Bestow. "It's important to communicate your wishes with loved ones so that if anything were to happen to you, they know how to proceed in your absence more confidently. Maybe you'd like a sibling to take care of your children, or you'd like to pay off your mortgage with a life insurance payout. Talking about financial plans—especially if the unexpected were to occur—can only better equip you and your family for the future."

RELATED: Everything You Need to Know About Estate Planning—and Why You Should Start Now