Worst Gift Flops Ever

When it comes to holiday buys, even the most fabulous of gifters have fruitcakes in their pasts.

Ricardo Rodriguez, real estate broker, Coldwell Banker
“Shopping for my friends’ kids—Chrissy and Max, the cutest you’d ever seen—I decided to get creative and bought little snow suits for them. They were sporty little children and already had so many toys, so I knew this would be perfect. All excited on Christmas Day, Chrissy opens it and immediately starts bawling, “I hate it!” And I look over and Max opens his and tears are streaming down his face. They’d laugh about it now that they’re teenagers, but I learned a lesson: Don’t give kids clothing—or tickets to things or little trips, I’ve tried those too—just give them toys. It’s all about the immediate satisfaction.”

Nirva, fashion designer
“Once, I decided to give my cousin was a book—the bestseller White Teeth. But I’d forgotten that she had just started working at a bookstore. She totally called me out on it, ‘Of all the years to get me a book… Of course, I’ve already read this!’ I didn’t have a gift receipt, so she kept it anyway.”

Jill Goldberg, owner, Hudson
“I’d flaked. It was three days before Christmas I hadn’t bought anything for my brother. Needing something quick, I ordered one of those six-tier chocolate towers for him from Harry & David. It obviously required no thought, but he appreciated it and ended up eating all six stories of calories and fat!”

Jennifer Hill, graphic artist, JHill Design
“The French parents of my close friend would bring me gifts on their holiday visits, and there’s nothing more stressful than reciprocating for a French person you don’t know very well. And there are only so many times you can give maple syrup. They were tea drinkers, so I bought a beautiful café au lait mug by one of my favorite potters. When they opened it they started speaking in French—the word “intéressant” was used—with confused looks on their faces and shunned the mug-bowl to back into its box. I felt so American and un-chic, but resolved to exclusively give maple syrup to the French in the future.”

Suzanne Cats, owner, LuxLash
“I overheard my boyfriend say that he’d always wanted to drive in an authentic track race, so I secretly got everything together to make his dream come true—the car, the suit, the helmet, the gloves, the fees and registration for the race, etc—and presented it to him at a party with a big red bow. But when we soon found out that the race I’d registered him for was a demolition derby, I was accused that of trying to send him to an early grave! He ended up participating anyway and had the time of his life.”

Jim Hannon, director, School of Fashion Design
“When I worked at Filene’s basement, I found the most amazing designer pieces. One year, I bought my brother this beautiful brown leather Ferragamo coat that I was so excited to give to him. But when he opened it up, he said, “I’m not a leather person.” Hello! I mean, this was a classic! So you know what I did? I kept it for myself. And I’m sure he regretted it a few years later.”

Storey Hieronymus, owner, Turtle boutique
“I had gotten my stepmother a gift for her first Christmas as part of our family but decided I needed to give her something more at the last minute. I picked out a little cookbook on Christmas cookies from my gift closet. I didn’t realize, however, that I was re-gifting it until she opened it up, and the card—to me, from someone else—was still inside. She was very gracious about it—didn’t mention it, just sort of tucked it away—but I’m sure she wasn’t very impressed. However, we’ve gotten along great since then.”