How to Deal With Awkward Money Questions Over the Holidays

The struggle is real.

Talking about your finances with folks requires tact and the right timing. But throw in some eggnog and a dinner table packed with extended family, and any hope for a reasonably civilized conversation about money goes right out the window. Depending on your family dynamics and your financial situation, heading home for the holidays means preparing to field some majorly awkward money questions. Consider it a cross-examination where the courtroom is the dinner table, and the jury includes a great aunt, a distant cousin, and some in-laws. Any good lawyer would advise you to prep before you take the stand, so consider us your counsel on all holiday money talk. We've compiled an assortment of awkward questions you might have to field this holiday, along with some tactful ways to answer—or deflect—them.

Is that a real job?

Whether you're one of the 37 million freelancers, starting your own business, working in the creative arts, navigating the startup world, or doing anything that your relatives might not consider conventional employment, the answer is always YES. Because that is the truth and because you shouldn't have to defend your chosen career and the goals you're striving everyday to meet. It's important when faced with this question that you answer confidently, if not for their sake, for your own.

When Jacqueline Whitmore, founder of The Protocol School of Palm Beach and author of the book Poised for Success, was starting her own business, she had to deal with this line of questioning over the holidays. "My answer back then was the first thing that came out of my mouth which was, 'I have a real job.' That's all I said. Sometimes that's the best answer," Whitmore tells Time. If you're worried you'll come off as defensive, Whitmore offers another tactic. Try saying: "I am doing what I love, and you know what they say, 'when you do what you love, the money will follow.'"

How much are you making?

File this question under one you never have to answer directly, unless you really want to. Your income is your business, and unless you're asking for financial help, you are entitled to keep your business to yourself—especially at the dinner table surrounded by distant relatives.

Wisebread's Emily Guy Birken suggests responding to the question playfully —"for instance, by saying "Half of what I'm worth, I'd say," or by placing your pinky against your mouth and intoning 'One million dollars!'" Then, feel free to change the subject. ("So, what's the secret ingredient that makes this stuffing so delicious?")

You're still living in that place?

Here's one you might get from a parent or sibling. Whether they're prompting a discussion about your investment strategy or pressuring you into home ownership, the question may be well-meaning, but it's also dripping with judgment and condescension—and that's no way to begin a productive financial conversation.

One tactic is to shut it down with a simple, "Yes, and I'm still very happy there, thanks." But if you really want to address the elephant in the room, state your case. There are plenty of solid reasons millions of millennials are choosing to rent their homes rather than buy—from a volatile housing market to lowered insurance costs.

"Be honest with your parents, laying out the ways in which renting is a better fit for you right now and how much better off your finances are as a result," suggests Learnvest's Marianne Hayes. "A big mortgage payment may have meant not being able to afford your plane ticket home, for example." If they won't listen to your reasoning, maybe they'll listen to Warren Buffett who believes the best investment you can make is in yourself.

Why don't you hire your cousin/invest in her company?

Yeah, this one is really awkward. One of your relatives is playing job recruiter, or worse, you're confronted directly by a relative who wants you to invest your hard-earned cash into a business that doesn't seem financially sound.

There's nothing wrong with helping out a family-member in need, but the holiday table isn't the best place for financial matchmaking. If your cousin needs a job, you can respond by saying you'll be happy to help in any way you can, but that you're not in a position to make hiring decisions at this time. Feel free to ask him to send you his resume in the new year, and add that you'll be happy to pass it along or keep your ear out for opportunities that might be the right fit.

If you're being hit up for a financial investment you're not comfortable making, you can be a bit more direct. "Instead of saying you have anything against the product or her method of doing business, just blame your budget," suggests Refinery29's money expert Priya Malani. "If it's not entirely true, think of it as a white lie for the greater good: 'I'd love to but it's not really in my budget right now. Thanks anyway!'"

Can I borrow some money?

The answer to this question all depends on who's asking. Is it a parent or sibling? Is it someone you trust with financial decisions? Is their need dire? And most importantly, are you flush enough to meet their requests?

"If you're able to take on the responsibility, pinpoint how much you're comfortable offering," writes Learnvest's Hayes. "In other words, lend only what you can afford to part with. From there, establish a clear payoff timeline and put the agreement in writing."

Still, Hayes suggests listening to your instincts before you jump into any agreement. "If the idea of loaning cash to little bro makes you uncomfortable, trust your gut," she writes. "Politely saying that you can't afford it right now is better than a ruined relationship down the line."

When are you going to find a stable partner?

This one is a doozy. You may be dating someone who isn't as financially stable as your family would like. Even if it's an issue you've grappled with in your relationship, it's not healthy or fair for your family to interfere with your romantic choices—financially or otherwise—unless you're soliciting their advice. Being too defensive can open a can of worms, and take the conversation further down a road you'd rather not go. Try citing a positive career shift your partner has recently made or touting an achievement you're proud of them for. Then, change the subject as fast as you possibly can.

Any other awkward question we haven't covered yet...

You may not be able to predict what you'll be hit with before the holidays, but you'll know an awkward question when it lands.

"If it's uncomfortable for you, it's probably uncomfortable for everyone in the room," Bethany Palmer of TheMoneyCouple tells US News and World Report. Do yourself and everyone else a favor and follow her blanket suggestion for shifting the conversation. Try saying this: "That's an interesting question – let's talk about it later?" Then, ask about dessert. Better yet, ask if you can replenish anyone's wine glasses. A glass or two more, and they might forget all about it.

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