In November, ahead of the holiday shopping onslaught, the fitness lifestyle brand Peloton released a 30-second commercial called “The Gift That Gives Back.” If, somehow, it hasn’t wound its way onto one of your screens, the ad centers on a youngish mom who receives a Peloton bike ($2,245 and up) from her husband and proceeds to chronicle her year of biking along with strangers every morning.

Regardless of whether one reads the ad as sexist (a man giving a woman a not-so-subtle hint to work out) or empowering (you can join an exercise community with a cult following without even leaving the house!), it is true that gifts like the Peloton bike, ones that promise life-changing experiences, are popular.

They’re also expensive. Consider Net-a-Porter’s six fantasy gifts ($8,110 to $294,900), which include a ski weekend at Saalbach Hinterglemm Leogang and a personal shopper to help the recipient build a new wardrobe.

Or Town and Country’s roundup of gifts for “the impossible-to-shop-for person on your list,” featuring a hot-air balloon over Mount Everest ($5,950,000 per person) and V.I.P. tours of Disney World (from $425 per hour). Though the price tags are, in a word, insane, and the gifts themselves do little to mitigate the environmental impact of giving season, the point is to bring people together.

“Community is the new luxury, right?” said Elise Loehnen, the chief content officer at Goop, in a recent interview. The website’s annual gift guide features several wellness retreats and treatments, which she recommends clearing with the recipient before buying. (“It’s like, ‘Hey Honey, I booked you for eight colonics,’ or ‘Hey, best friend, I thought you should go work on your unresolved trauma.’”)

Ms. Loehnen’s boss, the Goop founder Gwyneth Paltrow, tends to spring for “massages and anything that’s stress relieving,” she said. “Usually gift certificates.”

Celebrities, with their generous budgets and friends in high places, often excel at the experiential gift game.

In her memoir, “Stori Telling,” Tori Spelling recalls how her father, the producer Aaron Spelling, had a snow machine bring $2 million of fake weather to his home in Southern California so his children could have an unseasonable White Christmas. (Her mother is also fond of the holidays; her former home had three rooms dedicated to wrapping presents.)

The actress Kristen Bell once gleefully recounted the time her husband, Dax Shepard, rented a sloth for her 31st birthday.

This year, as a Mother’s Day surprise for her mom and grandma, Ariana Grande gave the gift of her presence.

The real cost of these kinds of gifts isn’t monetary (at least not for the rich and famous); it’s the stress of planning it. Trying to surprise someone with a road trip to a national park or a midnight tour of a museum or tea at the Plaza might involve snooping on the recipient’s schedule or telling a few white lies. For instance, what did that husband in the Peloton commercial have to do in order to get a stationary bike delivered to his home without his wife seeing it?

At Small Girls PR in Brooklyn, there’s a tradition of giving employees elaborate gifts for work anniversaries. “These range from round trips to the destination of their choice to Broadway tickets and Michelin-star meals,” said Mallory Blair, the company’s C.E.O.

“Historically, we coordinated these experiences with spouses, roommates, family members and snooping their Google calendar to arrange, until it trended toward a full-time job,” she said.

Now, with 64 employees, the company has established a so-called Glitter Committee of staffers who divide the labor of producing those commemorative moments.

They are sometimes victims of their own successful planning. “Two weeks ago I booked a couples massage for an employee on vacation in Belize. It took us four follow-ups with the remote hotel to get it done. I found out afterward she’d already booked and paid for a massage for the trip months earlier,” Ms. Blair said. “We switched it to a facial and dinner for two.”

Drew Zandonella-Stannard, a copywriter in Seattle, knows her husband’s taste well. This year, for Christmas, she bought him a bottle from the comedian Eric Wareheim’s line of natural wines and tickets to his stand-up tour. It was supposed to be a surprise, but the Postal Service ruined it. (Sorry, U.S.P.S., we love you.)

“Jacob signed for the wine, received the tickets via mail and opened both packages on the same day in November,” Ms. Zandonella-Stannard said. “Part of me wishes that we could all just agree to get each other exactly what we want, without maintaining this thin veil of surprise and delight every gift-giving holiday.”

Although gift cards have the same spirit — find your bliss! — they don’t pack the punch of a planned-out surprise.

“I wrote this huge essay on whether people should give gift cards or cash for the holidays when I was in college around 15 years ago,” said Jenny Fleiss, a founder of Rent the Runway and Jetblack.

“A transaction like a gift card doesn’t fulfill the need and intent of what gift giving is meant to do, so I said everyone should just give money. Now, with e-commerce, you can get everything from your fingertips, and it’s hard to find the special, unique twist,” she said.

Ms. Fleiss is buying her husband tickets to see “The Mentalist”; she told him ahead of time to ensure his schedule would be clear. “It busted up a surprise,” she said, “but it let me feel like I checked it off my list.”

The stealth and subterfuge of a surprise can become sort of performative, if not downright masochistic.

When Linden Ellis, a founder of the party goods company Coterie, found out some friends were going on a honeymoon in Maine, where she grew up, she thought she had the best, most New England welcome present idea in the land: lobster rolls waiting in their hotel room when they arrived.

Except then she started thinking about what it would take to make it happen. How could she figure out the hotel they were staying at without tipping them off? Their arrival time? Who could deliver lobster? What if they didn’t like lobster? It was all too much.

“I ended up Venmo-ing them with a note that said, ‘Your first lobster roll in Maine is on me.’”

In the end, it’s the thought that counts.