Even still, the most frequent request is simple on the surface: People want “a fun young guy,” or as Lawson interprets it, a handsome Australian or New Zealander in his 20s or 30s. (Women want to date them; men want to bro out with them.)

“We also get tons of requests for instructors with French accents,” says Lawson, adding that many clients want to practice their foreign language skills before heading to Courchevel or Megève. She jokes, “It’s like two lessons for the price of one!”

The Unspoken Rules of Attraction
Asking for photos before picking an instructor is a no-no at the Aspen skiing school (though it’s frequently attempted). And yet, there’s still an OkCupid-like quality to pairing students and teachers. Lawson and her team spend an average of 45 minutes on the phone getting to know each skier to find the perfect lid for every pot.

But just like in matchmaking, some clients are undateable. Have a habit of hitting on female pros? Chances are it’s highlighted and circled in your unwritten file, and you won’t be paired up with one again.

The worst transgressors even get little nicknames, like DHD. Dick Head Dad hasn’t just been barred from two Aspen hotels for being famously difficult, he’s also paid $685 for a half-day of guiding only to ditch the instructor after the first lift ride. (Being with an instructor enables you to cut the line.) Now when his requests come through, all the instructors tend to be busy washing their hair.

The Best-Regarded Celebrities Are Ones Who Like to Ski
In the staff locker room, celebrity names are dropped with the same excitement or indifference as a real estate titan or Wall Street trader—the only thing the pros care about is whether their clients like to ski.

A certain former first lady is beloved among instructors for her genuine affinity for slaloms. As for the current presidential couple? Not so much. Everyone still snickers about the massive blowup 30 years ago between Donald Trump and his first wife, Ivana, when she discovered he had brought along his then-mistress Marla Maples on their ski holiday. Legend has it that Ivana, who claims to have been an alternate for the Czechoslovakia Olympic team, followed him down the mountain skiing backward, berating him for his marital transgressions.

A lack of discretion is the easiest way to get mocked. One socialite, derided by Cam Short and his fellow ski valets at The Little Nell—Aspen’s most luxurious hotel—has a knack for loudly broadcasting her drug-addled exploits in crowded rooms. (“It probably helps her brand,” he reckons.) There’s the pop diva who insists on swishing around in a red leather bustier with her six brutish bodyguards—even in below-zero temps. Rebel Wilson scored jeers when she decided midmountain that she was done skiing for the day and insisted on a ride down from the emergency toboggan. And then there’s Jeff Bezos, who furrowed brows when he recently skipped a ski day for a shopping spree … on horseback.

Instructors Don’t Want to Catch a Whale
The instances of unruly guests or matches made in hell are fairly rare. Not so rare? Having skiers book an instructor for the entire season. Some families like to nab two—or even four! According to Aspen Skiing Co., the record-setting reservation blocked out three pros for 100 days ($250,000); second place went to a group that retained a personal skiing quartet for about two months ($184,000).

This pattern is most common among high-ranking members of the finance world, who offer their instructors to family members and colleagues just like they would a summer house. For instructors, this sounds like a pretty sweet deal. But actually most Aspen pros aren’t keen on being winter sports geishas. If their deep-pocketed patron decides to take one ski season off to spend the winter in Tahiti, it can send business plummeting—a risk that’s usually not worthwhile.