7 Awkward Holiday Spending Moments, Solved
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7 Awkward Holiday Money Moments, Solved

The weeks between Thanksgiving and New Year's Eve aren't just an excuse to break out your ugliest sweater, or to enjoy a regrettable evening of off-key singing at your office's karaoke-themed party. The holiday season is also a powerful financial stimulus that generates trillions of dollars for the American economy, with businesses employing about 768,000 seasonal workers each year.

Nestled within these trillions are plenty of ill-considered purchases, a cornucopia of good intentions, and an embarrassment of uncomfortable money situations. The bad news is that holiday-related expenses aren't going anywhere. The good news? Saving money during the holidays and avoiding awkwardness are easier when you develop a socially savvy financial strategy to handle some of the biggest money dilemmas of the season.

1. You decide to scale back on gifts — but don't want anyone to feel like they're on the naughty list

Every year you make a list — and every year you spend too much. Instead of blowing your budget on holiday gift shopping, get real about who you want to buy for and how much you want to spend. Manisha Thakor, Director of Wealth Strategies for Women at Buckingham & the BAM Alliance and author of Get Financially Naked, never shops for the holidays without a plan. "Decide whether you want to go narrow and deep or wide and shallow," Thakor says. In other words, buy expensive presents for your closest family only, or spread the cheer and give cheaper gifts to more people. Whichever approach you choose, keep your total budget the same.

Avoid hurt feelings by discussing expectations with your family members, friends, and coworkers before you shop. No matter how awkward you might feel about cutting back, own your strategy, and others may follow your lead.

2. "But Mom! I totally NEED a new phone!"

Let's face it. Kids don't always have the easiest time defining the boundaries between needs and niceties. You want to buy presents for your kids that they'll love, but you also don't want to blow a healthy chunk of your holiday budget on an expensive gadget that lasts a few months without breaking — and that's if you're lucky.

Your best bet? Have an honest talk with your children about your family's holiday spending plan, choose smarter options together, and make sure the shopping that follows aligns with your stated goals. Want to take the sting out of the delivery? Tell your kids that by spending less now you'll be able to do more on your summer vacation later.

3. Can't somebody else host dinner?

When you're the only person in your family who knows how much a fresh turkey costs per pound, it's time to share the love. The dinner tab love, that is.

Whether you prepare your holiday meals at home or you prefer to dine at a restaurant, hosting family and friends is expensive, not to mention stressful — especially when you're in charge, year after year. If your guests have become a little too accustomed to enjoying your holiday hospitality — or you're simply tired of always footing the bill for entertaining a large crowd — then make tactful diplomacy your new best friend.

Have a chat with your guests in person or over the phone, not over text. Keep your message simple and direct: you're dialing back your stress level by cutting down on entertaining, and you'd like to discuss ideas for turning your next holiday gathering into a group effort. That could take the form of a potluck Thanksgiving or simply splitting the bill when you dine out. Who knows? Maybe someone else in your family is dying to host — and in that case, offer to bring a side dish, flowers, and a bottle of wine.

4. Grandma's gone wild

You give your kids a small number of thoughtfully chosen, carefully wrapped presents. Your mom lands at your home with gifts so vast in quantity that you could open your own toy store. How can you get grandma to tone it down without sounding ungrateful?

Asking well-meaning grandparents and relatives to cut back on gift giving can be tricky, especially since sensitive loved ones could interpret your request as rejection. Again, in-person or telephone conversations are best.

Convey your appreciation for the gifts they've given in the past, but also that you want the holidays to be about spending time together rather than opening expensive presents.

Coordinate with family members before they shop so you know what's coming. As your kids grow older, scale back gift-giving to one present per child, or opt for family reunions instead. "We don't do gifting anymore," Dean K. of McAlester, OK, says. "We only travel to visit one another. It took all the holiday stress out of our lives. I do like to open a present, but we would rather have an experience than another gift."

If your family members insist on purchasing presents, there are several alternatives. Try suggesting a contribution to an education savings fund or a gift exchange. Alternatively, "experience" presents, such as concert tickets or a restaurant gift certificate, are holiday winners family members will enjoy giving that won't gather dust on your shelf.

5. They spent high, but you spent low

What's the fastest way to ruin a special holiday moment? The shameful, about-to-be-revealed knowledge that the gift you're giving cannot possibly match the grandeur of what you just opened.

"There's nothing worse than getting a diamond bracelet and you gave homemade cookies. And the cookies were better than the bracelet," Dean says.

Nevertheless, "no one wants to be in the jungle of tit-for-tat," he continues. "The holidays are about making other people happy, but if you reciprocate for no good reason other than you feel you have to spend a lot of money, then no one is happy."

If this happens to you, don't make excuses, and definitely don't up the ante by rushing out to purchase a more expensive gift — unless you want to repeat the experience next year. After receiving an extravagant piece of jewelry from a friend one Christmas, Dean tactfully returned it to her. "I included a note saying how much I appreciated the gift, but that I just couldn't accept it. Sometimes, you just have to say, look, I love you and we are really good friends. But this is over my threshold. And I don't want our friendship to be about gifts.

"I try to know what the person really likes, or to give something that would mean a lot to me," he adds. "Sending flowers from a favorite florist, or giving a luxurious card deck to a bridge player," for example, "are sincere but affordable ways to show you care."

6. Ugh! The office grab bag!

Just when you think you have your holiday budget under control, you realize you haven't purchased anything for your coworkers. For many people, that means one thing: more shopping. And to make matters worse, you just remembered that it's your year to organize the office holiday party.

"Office gift-giving gets completely out of control," Thakor observes, especially when a smallish group of 10 grows into a large group of 35. Gather your coworkers to discuss skipping individual giving in favor of participating in an optional gift exchange, so each participant only has to purchase one present. Check your office's employee policy manual to learn if your workplace defines appropriate dollar values. If it doesn't, aim for no more than $10 or $20.

If you're new to your workplace then participating in a grab bag is a nice way to grow closer with your coworkers. But if you'd prefer to pass, simply smile and decline graciously. Bring in a plate of cookies or candy instead to share your goodwill.

7. 'Tis the season for tipping — but how much should you spend?

Daycare teachers, nursing home employees, building service staff members, trash collectors, salon workers, and housecleaners are just a few of the professionals who keep our lives running smoothly. Show them how much you appreciate their hard work with a holiday tip that is generous but appropriate.

Not sure how much to give? Review etiquette guidelines for seasonal tipping and get it right. No matter who you're gifting, include a handwritten note that shares sincere good wishes for a wonderful new year. And remember, the holiday spirit lives in our hearts, and not in our wallets.

Holiday Tipping Checklist:

Before you give, make sure you check your local regulations, school, and company policies first. Some municipalities don't allow tipping city employees, and many companies and organizations have strict gift-giving policies.

Kate Ashford
Lisa Bigelow is a writer and editor who specializes in personal finance and lifestyle topics. She lives in Connecticut with her husband and three children.

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