How to Navigate Awkward Money Conversations at Your Family's Holiday Dinner

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Multi Generation Family Celebrating Thanksgiving
If you're going to visit family on Thanksgiving and Christmas, you have a lot to look forward to: home-cooked meals, gifts under the tree, and catching up with your cousins and other extended family members.

What you're probably not looking forward to? Being quizzed by your parents about your career, your marital status, and your finances.

'I Don't Want to Talk About It'

The last thing you want on your visit home is to find yourself being interrogated at the dinner table about, say, why you're still living with roommates at 30. Or how much money you're making. Or why you're jobless or underemployed, despite that expensive college education.

If your parents or members of your extended family are the type to ask such awkward questions, you'll need to be prepared to deftly answer them without giving away too much -- and without turning Thanksgiving dinner into a Lincoln-Douglas debate about your 401(k). Here are a few tips:

Go in with a plan. You probably have some idea of which aspects of your life are going to inspire questions, so you want to be prepared.

%VIRTUAL-article-sponsoredlinks%"If I know that I just graduated from college in May and I'm not yet employed, the obvious question is, 'When are you getting a job?'" says Jodi R.R. Smith, founder of the etiquette consultancy Mannersmith. "So I might pre-empt it -- I can say, 'I'm doing great, I'm working on some temporary assignments that might turn into work.'"

By getting on top of the question before it's asked, you'll be able to present your situation on your own terms.

Don't overshare. "It's really about being tactful and knowing your audience," says Erin Lowry, 24, who blogs about personal finance at Broke Millenial. "There are certain parts of living the NYC lifestyle that I don't tell my grandma, like that I could barely afford to feed myself when I moved here. Gloss over details, or omit them."

Deflect with humor. Smith says there's one sure way to shut down an awkward line of questioning from a nosy uncle or a grandparent who no longer feels the need to be tactful: Make a joke.

"If they say, 'It's about time you got a job' or 'how much are you making?' you can tell them, 'I'm very happy based on what's going on the economy, and I can support myself -- but if you want, you can leave me money in the will,'" she suggests.

Starting the Conversation

The flip side to these tips is that sometimes, you'll be the one starting the awkward money conversation.

"We see an uptick in questions about long-term care around the holidays," says Jody Gastfriend, vice president of senior care services at That spike is largely due to people going home to see their elderly parents, and spotting worrisome changes in how they're taking care of themselves. "There may be some changes in their ability to tend to the house, or maybe the medications are expired -- there's a whole range of things people notice," she explains.

Before you launch into a conversation about assisted living facilities at the dinner table, though, Gastfriend has a few suggestions.

Talk to your siblings. You'll want to get all the offspring involved in coming up with a plan, especially since you'll all probably wind up footing at least part of the bill -- one way or another.

"There's often sibling discord about money and perception of need," she says. "Getting together so conflicts don't arise when approaching the parents is important."

Take it slow. Gastfriend says you shouldn't just go to your parents and present a plan -- you don't want to make it seem that you're coercing them. And you might start by suggesting small changes to their living situation, rather than, for example, immediately proposing they move to an assisted living facility.

"Incremental changes can lead the way to receptivity down the road," she says. "Maybe start by just bringing someone coming in once or twice a week to help with groceries." As they get used to being taken care of, the decision to relocate to an elder-care community will seem like less of a leap.

Don't bring it up at the holidays. Thanksgiving or Christmas might be a good time to have a preliminary discussion about long-term care with your siblings. But unless Thanksgiving or Christmas is the only time when the family can be in one place, you should avoid having the big talk during the holidays.

"We often tell families, don't do it at the holiday itself," she says. "Sometimes, it's too loaded a topic."

Matt Brownell is the consumer and retail reporter for DailyFinance. You can reach him at, and follow him on Twitter at @Brownellorama.

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How to Navigate Awkward Money Conversations at Your Family's Holiday Dinner

Elmo was popular when I was a kid. He was popular in the mid-90s, when America went insane over Tickle Me Elmo dolls. And with the toy appearing on all three lists, it looks like he'll be popular this year, too. 

Centuries from now, when humanity has migrated to the stars, we'll still give our kids Elmo dolls for Space Chanukah. 

Here's another ghost of Christmas shopping past. Kmart and Walmart are both bullish on the latest Furby, which according to the product description "has a mind of its own." It goes on to say that "the way you treat your Furby will shape its personality." Incidentally, you could also describe children this way. Expect to pay around $60 for this one.
Doc McStuffins follows the adventures of a veterinarian who operates on stuffed animals, and the dolls and play centers promise to be popular again this year. All three retailers have this playset on their lists, though it should be noted that Toys R Us exclusively has the "Deluxe" version of the kit pictured here. The Deluxe set has 14 bonus pieces, including a fetching pink labcoat. Note that the Deluxe costs $79.99, versus $64.50 for the standard set at Walmart. 

Toys R Us is building tablet mini-shops in its stores, so clearly it expects kid's tablets to be a big market this season. Both Toys R Us and Kmart have the LeapFrog on their lists this year. 

The tablets cost $150 and is durable enough to withstand drops, though it's not waterproof. So if your kid is prone to pitching toys into the toilet, steer clear of this one. 

The Ninja Turtles are going to be big this year. At Kmart you can find this remote-control "Shellraiser" vehicle, which shoots sewer covers and costs around $45. At Walmart there's the Secret Sewer Lair playset, which costs $80. And at its holiday preview event last week, Toys R Us had classic Ninja Turtles figures and their "party wagon" on display. 

Basically, you can't go wrong with Ninja Turtles. (Which, incidentally, is what I tell my parents every year when they ask what I want for Chanukah.)

Both Kmart and Walmart list this one, so it looks to be this season's hot Nerf gun. As the coloring and name make clear, it's a toy weapon being marketed to girls, a rare move for Nerf. We're thinking the popularity of archery-centric movies with teen girl protagonists like "The Hunger Games" and "Brave" account for Nerf's sudden interest in selling to the female market. 

We don't recall Princess Merida or Katniss Everdeen using a hot-pink-and-purple bow, but hey, that's toy marketing for you. This one will cost $15.99 at Walmart.

Unlike other fairy dolls, this one actually flies. It must be a real fairy!

No, just kidding, it's just a toy. Get it for $30 at Walmart. It takes six AA batteries, which aren't included.

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