One concierge dishes anonymously from behind the hotel desk. 

It never stops surprising me how often guests love to stop to chat about the “amazing coincidences” they experience while visiting Aspen, a place well traveled by the jet-set community. Often, usually over the holidays, guests will stop by and recount how they are blown away by the fact that someone they just met at Soho House in New York was at the very same restaurant they were at tonight, or how their child’s friend from boarding school was skiing at the same mountain and they ran into each other on the lift, or that the family that has the house next to theirs in the Hamptons is staying in the same hotel! How odd! I have to act surprised, but it’s like running into someone you know at City Market; there are only so many places the extremely wealthy can be at any given time.

Being a concierge in Aspen means fielding some bizarre requests and listening to visitors’ perceptions of small-town living. 

We are often asked to help plan marriage proposals, and these are usually pleasant tasks because the guests are very appreciative of our efforts to make the event a special memory. However, you would be surprised to know how much time and effort are spent talking (usually men) out of their awkward initial plans. In one season alone, I talked two different gentlemen out of proposing to their girlfriends inside their hotel room. 

My normal lecture to them points out that, 20 years from now, his wife will be telling her friends about her husband got down on one knee in front of an ottoman, next to a piece of luggage, and pulled the ring out from under a glossy luxury lifestyle magazine… and how much she’s not going to like telling that story. Instead there are a half-dozen romantic places nearby that with minimum effort will be far more charming than, sigh, a hotel room. Even worse, I’ve had to give a firm, “No!” to a few guys who wanted their server at a restaurant to bring out the ring in the bottom of a glass of champagne with their dessert. I wish I had a spray water bottle at the concierge desk for these occasions so I could spritz their face while I say, “No! Bad boy!”

Many of Aspen’s visitors live in cities and they believe that any two places are separated by vast distances. Recently a couple came by the desk one morning to complain that the night before they had been stuck at a restaurant for hours because they were celebrating until after our hotel shuttles stopped running for the evening. They had to wait until the restaurant closed and the manager could give them a ride back to the hotel—four blocks away. Another guest was having a meltdown because Aspen doesn’t have Ubers, and actually said, “What type of ridiculous town doesn’t have Ubers? This town is tiny, you can walk everywhere, it would be so easy to be an Uber driver!”

Of course, many of Aspen’s guests are used to getting whatever they want, because in most parts of the world where they travel they are considered extraordinarily wealthy and powerful. Here in Aspen, they are just another person on the street. Recently a guest wanted to smoke a cigar somewhere inside and the Cigar Bar wasn’t “cozy” enough. The guest was shocked that everyone in town was telling him no, and it seemed impossible to him that the only reason could be the  “just the law.” I called around and found a couple of places that would be able to close down for a private buy-out and let him sit and smoke to his heart’s content, all alone. In the end he didn’t think a five-figure fee was worth it.