Your brother wants to borrow money, but he never paid you back the last time you lent him cash
“If you’re going to give money to a family member, you have to think of it as a gift, and accept that you may never see it again,” says Rowley. “Loans that are never paid back can destroy relationships.” Not ready to part with your cash forever? In that case, Rowley recommends handling the loan in a more professional manner by using a service like LoanBack.com, which helps you create a legally binding loan agreement, or LendingKarma.com, which lets you document and track your loan. However, if you’re simply not comfortable lending money to a relative, your best bet is to just be honest. “Rather than just saying 'no' and risking resentment, give him a concrete reason that you can't help him out. Say that you’re saving for your kids’ college fund or are earmarking the cash for groceries.”
And if the deal has already transpired? Rowley recommends picking a time when money will change hands — like while you’re getting coffee together or are out to dinner — to remind him about the loan. When the check arrives, consider saying something like, “Since I lent you $20 last month, why don’t you pick up dinner? Then we’ll be even.” When larger amounts of money are at stake, consider writing an email so he can save face in case he forgot about the loan or isn’t able to pay you back right away.
Your friend always chooses restaurants that are out of your price range.
We all have that friend with extravagant taste — and a paycheck to support it. But what if you can’t keep up with the fancy dinners and expensive outings? “Be a connoisseur of free events, so you can offer a few creative countersuggestions,” Rowley advises. If your buddy wants to get drinks at a swanky bar, suggest meeting there at happy hour when drinks are less expensive. Or recommend a free event that's on par with her interests, like a gallery opening or free concert in the park. If it's a really good friend, just be honest: Tell her you can't afford to pay top price for cocktails this week and suggest a less pricey bar. And let her know that she can choose a fancier pick at a later date when you're not having cash-flow issues.
Your work friends all want to go in on a gift together, but no one can agree on a fair amount to contribute.
In this situation you want to take control and be the money collector, says Rowley. Decide what you’d like to contribute, spread the word and welcome everyone else to chip in as much as they’d like. “But you have to decide that you won’t be resentful of people who give more or less than you did.” If you’d rather settle on a more uniform contribution, send out an email asking everyone privately what range of amounts they’re comfortable giving, suggests Lizzie Post, spokesperson for the Emily Post Institute. “Once you’ve collected the high and low end of everyone’s budget, you should be able to figure out something that will work for everyone.”
Your sister, who makes more than you, always insists on picking up the check when you two go out.
If you’re temporarily cash-poor — say, you’re in school or going through a divorce — then take your sibling up on her kind offer to treat you and know that you’ll return the favor when you’re back on your feet. But if it’s a chronic situation where she makes more than you and refuses to let you pay, “find a way to reciprocate that makes sense financially,” says Rowley. When she hands over her credit card, “invite her over to dinner at your house or offer to babysit her kids so that she can have a night out. You’re still paying her back — but in a way that you can afford.” If you continue to feel uncomfortable with the dynamic, sit down with her and express your feelings. Then brainstorm things you two can do together that don't require one of you to always pull out your wallet. This is also a good way to settle the money issue once and for all, especially if you sense that she may feel resentful about shouldering all of the costs.
You want to ask your friends and colleagues for a charitable donation.
Whether you’re running a marathon to raise money for an important cause or seeking contributions for your church’s canned food drive, the last thing you want to do is make people feel put upon. “Don’t solicit individuals in a group setting, which can put pressure on them,” advises Post. Approach them individually so they’ll be more comfortable, regardless of whether they're pulling out their checkbook or declining to contribute. Even better: Send out an email so people can decide for themselves whether they’d like to donate as well as have time to answer honestly without being caught off guard or feeling pressured. For those who do contribute, always send a thank-you card or homemade treat to show your appreciation, so they don't feel their donation went unnoticed.
Your friend is a seamstress and offers to hem your pants — all five pairs.
“Always offer to pay her,” says Post. “Chances are, she’ll say ‘Don’t worry about it,’ but don’t be shocked if she doesn’t.” If she does hem your pants — or style your hair, or give you decorating advice — gratis, a gift or gift card is a great way to thank her for the service she provided. But be careful when it comes to soliciting professional advice from friends. If you’re asking for legal counsel from your lawyer buddy, be upfront and admit that you aren’t sure what crosses over into billable-hours territory. This gives her a chance to say what she’s comfortable advising you on for free.
Your friend is in a tough spot financially and you want to help without offending her.
Many people are too proud to accept help — even when they truly need it. If your friend turns down an offer of money, but you still want to lend a hand without making her feel uncomfortable, Rowley recommends GivingAnonymously.com, a website that allows you to make a financial donation without revealing who you are. “It’s a good way to do something nice for your friend without changing the power dynamics of the relationship.” You can also help out in a non-monetary way, whether it’s babysitting, giving her kids hand-me-downs or bringing over a casserole.
The parents of your son’s best friend offer to take him to an amusement park, without bringing up who’s paying.
“I would always offer to pay your child’s way,” says Rowley. “If they refuse, send money with him to the outing — sometimes it will come back unspent, and other times it will be spent.” If you can’t afford to pay, offer to reciprocate in another way. For example, you can have their kid over for a sleepover so his parents can go out to dinner (often the gift of time is even more appreciated than money). And if your first thought is to feel offended, look at the bigger picture: Maybe the friend’s parents work long hours and want to reciprocate for all the time their child spends at your house, or perhaps they have an only child who doesn’t have any siblings to share the amusement park experience with.
You always host family holiday gatherings and no one ever offers to chip in.
Change the tradition and host a potluck, says Post, whose own family hosts a 20-person Thanksgiving where everyone is assigned an item to bring. Make sure everyone knows well ahead of time that things will be different this year, and let people volunteer to bring something before you start assigning recipes to make and chores to do — otherwise you may come across as being bossy. Another option is to email a list of needed items that people can sign up for. “You want to have lists and tasks ready so everyone knows what they’re responsible for,” Post says. And, to avoid hurt feelings, keep Rowley's advice in mind: Always add non-monetary tasks to the list — like organizing the sack race or coming up with a seating plan — so relatives who can’t afford to contribute financially can still be involved.
You have one friend who never tips or contributes enough when you go out and you always end up pitching in more money to make up for it.
In this instance, you really have to decide how much you want to include your friend. Even if she’s only shaving off a few dollars each meal, it adds up over time. If you truly enjoy her company, get out the calculator and be forceful about how much each person is required to contribute when it comes time to pay. “Or, maybe this is her way of saying that she can’t afford the meals,” suggests Rowley. “Try meeting for breakfast or lunch instead of dinner and see if anything changes.” If not, it may be best to hang out with her at one of your homes, where no one needs to pull out a wallet.