The only thing more stressful than shopping for holiday gifts—especially at the last minute—is shopping for bathing suits. In both situations, you’re surrounded by bad lighting and feelings of inadequacy and regret.Gift giving is often loaded with anxiety because it marries high expectations with immediate feedback: As soon as your husband or mother-in-law unwraps the present, you know right away if they truly liked it (“Wow, this is so great!”) or didn’t (“Oh, how nice”). So it’s no surprise that many of us have cracked under the present pressure, leading us to purchase criminally bad gifts, from the cheetah print Snuggie to a horrible maroon tie (maroon? Really?). Or else by throwing money at the problem by buying an over-the-top, unnecessarily expensive gift when you come up blank on ideas.So why do we put ourselves through this torture year after year? To boost our bond with family, friends and our bosses, according to Art Markman, Ph.D., YouBeauty Psychology Advisor. “We give gifts to cement family relationships and to solidify certain kinds of work relationships,” he says. “With couples, it’s a way of saying, ‘I was thinking about you and I know you.’”QUIZ: How Healthy Are Your Relationships?Adds Frank Flynn, Ph.D., Paul E. Holden professor of organizational behavior at the Stanford Graduate School of Business: “There are all kinds of reasons people give gifts. Typically, they want to be appreciated by the person they’re giving it to and hoping to not disappoint people and delight them. That can create stress—that they’re going to disappoint the person they care about. It can be an opportunity to fail or succeed.”Choosing the wrong gift can be a major fail because it can leave the gift recipient feeling like you don’t really know or understand them or that you didn’t bother to give the purchase some real thought. Remember that episode of “Sex and the City” when Mr. Big bought Carrie an expensive duck-shaped Judith Leiber purse? She was so distraught because it was the complete opposite of her sense of style and she felt he didn’t really “get” her after all. “When someone gets you a gift that misses the point, you look at it and think they don’t really know me,” says Markman.MORE: Gratitude Is Good for HealthBoth gift givers and receivers agree that the best presents convey thoughtfulness and consideration—namely, that you’ve thought of the gift recipient as significant, special and as an individual, according to Flynn. “But givers and receivers don’t always agree on what gift sends that signal,” he says. And in some cases, the gift giver is completely wrong and overly-confident about their ability to pick the right present. “The classic example is a wedding,” says Flynn. “On the wedding registry, the couple asks for towels and flatware. The guests think, ‘If I give them towels, how are they are going to appreciate that? I should give them something unique.’ But when the couple receives it, they think, ‘I told you what we wanted and you totally ignored us.’ How is that conveying thoughtfulness? It’s saying, ‘No, I know what you want.’ Everyone has a story of a well-intentioned and expensive gift that’s off-the-mark.”GALLERY: Holiday Gifts that Give BackInstead of kicking yourself over the gift you should have gotten and wasting your hard-earned money, keep these tips in mind when you head out on your next holiday shopping excursion:Focus on the person receiving the gift. Rather than picking up the Crocs your cousin wanted, you decide to get her the sexy black boots you’re secretly coveting, thinking she’ll love them. And then you can’t believe it when she doesn’t flip over them.There’s a reason we buy gifts we think our loved ones should enjoy rather than the presents they’re truly drooling over: It makes us uncomfortable to buy gifts that go against what we like. A study published in the Journal Consumer Research found that when people bought gifts that matched the identity of the recipient but conflicted with their own identity—say, a vegetarian buying her boyfriend a leather jacket—they felt uncomfortable. What’s more, it also motivated the gift giver to then go out and purchase something that’s more in line with her beliefs.Avoid the gift receiver’s inevitable disappointment and ensuing awkwardness by focusing on the person getting the present and asking yourself, “What would they really like to receive?”STUDY: Conscientious Lovers Are More CaringStart a family-wide wish list. Create a shared Google spreadsheet in which you and your partner as well as your family have their own column where they can jot down their gift wish list. This may sound like it would take all the fun and surprise out of gift giving, but it actually helps eliminate stress and disappointment. You know exactly what to get them—and they’re thrilled to receive something that they truly want. “The beauty of lists is for those whom you’re not quite as close to on a daily basis,” says Markman. “It gives you a chance to get something for someone that will be appreciated. Everybody wins.”Don’t get caught up in the price tag. It’s easy to assume that the more expensive the gift, the more it will be appreciated, but that’s not necessarily true. A study in the Journal of Experimental Social Psychology found that, despite the fact that gift givers expected a correlation between how much they spent on a gift with how much the gift-recipients appreciated the gift, the research found there was no connection between the magnitude of the present and their actual feelings of appreciation.What’s more, giving a pricey gift to family members who might not be in your same financial situation can backfire. “A lot of what you’re communicating is ‘I can buy you something expensive,’” says Markman. “Think about families where there are disparities of income with siblings. The gift is saying, ‘I can do this and you can’t.’” It doesn’t exactly make for a warm and chummy holiday.MORE: Too Pricey? Try LayawayAlso, spending a fortune on a gift and not having the receiver respond in the way you’d expected—namely, screaming with a level of excitement normally reserved for teens at a Justin Bieber concert, followed by exclaiming that you are the best gift giver to ever walk the earth—can leave you feeling angry, disappointed and sad about the money you essentially wasted.Put some heart into the present. A small sentimental gift can go a long way if you put some genuine thoughtfulness into it. “Sometimes the worry with homemade is if I spend no money, does that suggest I don’t really care about them?” says Flynn. “But it’s not true. It’s the thoughtfulness and consideration that drives the gift.” For example, what’s better than creating a picture book for your partner through Kodak Gallery or Blurb with photos from when you first started dating, your traveling adventures, your wedding and the birth of your kids, along with some sweet or funny captions? What makes the gift so special is that it’s loaded with heart and could only come from you. “Look for something that speaks to that person and makes them feel understood—which is not the most expensive thing you can get,” notes Markman.Or go for cold, hard cash. People often worry that giving cash for a present makes it look like you took the easy way out or that a physical gift is better, but that’s not so. “For example, for a lot of people who are young and married, giving cash shows consideration of what their real needs are,” says Flynn. “It can be awkward for them to say give us money, but when someone does that, it’s really appreciated.”COLUMN: The Truth About Money and HappinessBut the thoughtfulness goes both ways: If someone gives you cash as a gift, mention in the thank you note what you’re planning on using the money towards, such as a new set of dishware or a couch you’ve had your eye on. After all, the real pleasure of giving presents is knowing you made someone’s day—and got it right.