First comes lust… 

As I unzip my boots in the foyer of a stranger’s apartment somewhere by the S-curves, the clock reads 2:30 a.m. On the heels of a raucous evening spent hopscotching downtown watering holes, my shred buddy/wingman has brought me here, to an after-party. Down to socks, I stand up beside him to see the front door open—and lock eyes with a new-to-town dude who didn’t call me after a few great dates two weeks earlier. (To be fair, I didn’t call him either, on principle.) In this moment, the flurry of ironic truths about dating in Aspen is dizzying: You will run into a former flame when you least expect it; platonic friends of the opposite sex are always presumed romantic partners, fodder for the small-town rumor mill; and successful courtship seems to require more effort than elsewhere—for recent transplants, especially. 

No doubt, Colorado mountain towns are strange places to mate. Almost every woman from ski meccas spanning Durango to Breckenridge has at one point uttered the expression, “The odds are good, but the goods are odd”; guys respond, “You don’t lose your girlfriend, you lose your turn.” 

Aspen, of course, is in a class all its own. While off the beaten path geographically, much like Telluride or Crested Butte, our fair city is very much on the radar of the beautiful people. Its inhabitants are also athletic, intelligent, and charismatic, with worldliness to match. Independence and adrenaline are the two most coveted drugs, and our rich social playground cultivates euphoria and debauchery—in particular after dark. So it should come as no surprise that scouting a soul mate, or even just a steady, in this hedonistic yet cerebral utopia is as complex as the fickle weather discussed during a bad first date. 

Then comes distraction…

Why are you single?” Where I grew up, that question would carry a twinge of suspicion. But after three years in Aspen, I’ve realized it’s rarely taken seriously here. This is good news for many of us—straight, gay, in-between—because it means that eschewing the shackles of commitment during one’s first four decades isn’t shady; it’s par for the course. Then again, I’ve only been here three years. And I’m only thirty-two. If a biological clock is ticking, I haven’t heard it yet. 

I’ve got a decent dating profile, too. I’m a tall, blonde, adventurous, educated, creative professional from an adoring East Coast family. Friends of diverse backgrounds agree: I’m affable, trustworthy, and free-spirited, with dozens of interests and few grievances. I’m also impulsive, prone to recklessness, and stubborn beyond reason. Rarely am I without rose-tinted goggles, and though a social butterfly by nature, I’m a lone wolf at heart. In other words: I’m Aspen Average.

Venturing out at night here can seem like stepping into a low-carb beer commercial. Each winter and summer welcomes an influx of youth, a largely seasonal workforce hailing from exotic corners of the globe: South Africa, Australia, Argentina, the Philippines. Many full-time residents fled the bright lights and big cities for a simpler life in the mountains—though they’ll head off to explore faraway locales a couple of times a year, adding to Aspen’s cosmopolitan aura when they return. Education is a barometer—61.7 percent possess bachelor’s degrees, appreciably above the Colorado state average of 37 percent. But perhaps the most discernable ingredient in the strange brew of the Aspen singles scene is the fact that, for lack of a better cliché, we all feel exceptionally young at heart. Might the grains of sand in the hourglass fall more slowly at altitude?

“I have Peter Pan syndrome,” declares a fortysomething chef, echoing scores of proud men spanning post-graduate ski bums to fiftyish restaurateurs. “I become younger every year. I want to maintain that.”

A forty-year-old divorced bartender listening in says he, too, has embraced a similar regression since moving here in the 1990s—the decade in which many of his fellow service-industry workers were born. “This town is like college,” he says. “It’s always somebody’s Friday.” 

The Peter Pan symptoms are easily discernable. Most of those afflicted exhibit a disinterest in achieving traditional adult milestones: building a career, getting married, raising children. Women are not immune, either. (The iconic Disney character is often played by female thespians, after all.) Whereas grown boys may not feel the tug of time as it marches them toward physical ruggedness, for us it’s a darker seduction. As the ladies hawking lotions and potions at Cos Bar know well: Our harsh climate doesn’t quite align with the expectations of female beauty. We might feel like carefree kids in a candy store—until we don’t.  

“There’s a lot of competition,” says a thirty-four-year-old real estate agent who describes herself as an athletic brunette. “There are more opportunities for women who are anorexic workout maniacs with lots of plastic surgery and peroxided hair. There’s some sort of ideal in Aspen for gentlemen who prefer that type. I’m not that type. That’s discouraging.”

She does admit that there seem to be a lot of cute dudes from which to choose. (And I concur!) But it’s not quite the mountain-hunk HQ we assume. As it turns out, Aspen’s advantageous male-to-female ratio is grossly exaggerated. The 2010 US Census pegs women at 47.9 percent of the local population, compared with 49 percent across the state. Hardly the eight-to-one guy-heavy figure bandied about in conversation.

What Aspenites might lack in maturity, however, they more than make up for in fearlessness—whether hucking cliffs or inviting themselves over to spend the night—occasionally at the expense of decency. We are driven by pursuit of the extreme, be it skiing, cycling, mountaineering, or chasing luxury and wealth. In fact, Pitkin County is the fittest part of Colorado, the fittest state in the country. That’s a good omen for singles, as research suggests people find dates more attractive after heart-pumping activities. 

A caveat: Living among passionate risk-takers can easily incite bad behavior. “Monogamy is not necessarily an unchallenged situation,” says a thirty-four-year-old retail associate from the Midwest. “Life here can be great if you find the person you adore. But the second you walk out the door without that other person, you’re in this town where everybody’s on vacation or ready to make a move and have fun. It’s like you took a flight out to Vegas—what happens here stays here.”

That is, until it doesn’t. “Mind your reputation,” a graying spinster once warned me at Campo de Fiori. Her message was clear: there are only so many dark corners in Aspen. Screw up socially, and a cocktail named for your indiscretion might make the menu at Justice Snow’s. Ask a bartender there for the story of “the PDA.”

THE USUAL SUSPECTS 
The Aspen hodgepodge is sociologically diverse. (Ethnically, not so much.) But you’re bound to encounter these five archetypes. 

THE PASSIONATE PARTIER
Shots of Tuaca at Esco Patio at noon on a Tuesday? They’re in! 
Upside: While you might sit solo as they air-kiss half the room, these raging animals boast the best hangover cures. 
Risk factor: Too many to list, including VD and their (and possibly your) occasional jaunts to rehab. 

THE UPRIGHT
Citizen: Works in Aspen Skiing Company management or at a local architecture firm. In fact, moved here for a real job ten years ago.
Upside: Suburban relationship ideals—in Aspen.
Risk factor: Competition for this catch is steep. A tough wedding at which to be maid-of-honor/best man. 

THE ADVENTURE
Fiend: Whether climbing peaks or schussing down ’em, this über-athletic, amped-up adrenaline junkie lives in the moment. Must love dogs!
 Upside: Owns so much gear you don’t need to buy any; a built-in mountaineering guide; and “beast mode”: hot!
 Risk factor: No friends on a powder day—that includes you.

THE TRUSTAFARIAN:
From nonprofit directors to self-indulgent dilettantes, these silver-spoon-fed kin do whatever they want and drive cars costlier than your annual salary.
Upside: A parking spot on Sardy Field; Caribou Club bar tab; weekly omakase at Matsu.
Risk factor: A not-so-subtle sense of entitlement—to the Next Best Thing—or a decidedly unromantic prenup, should the relationship progress that far.

THE CREEP: A guy, generally, who can smell a fresh Aspen import from atop Highland Bowl. While you might not notice his egregious lack of social decency at first, beware: he will leer, jeer, and hijack the moment at first opportunity.
Upside: None. Run for it!

SCENE AROUND ASPEN
Since downtown Aspen comprises just a half-dozen city blocks, changing scenery is as easy as crossing the street. Here’s where to mingle if you’re single:

RESTAURANT BARS
Aspen’s oldest restaurants are home to the liveliest bars. If Tom Cruise had worked in an Italian trattoria in Cocktail, the setting would resemble Campo de Fiori, a quintessential pick-up spot stuffed with hotties. Unbuttoned bartenders are unabashed in creating an atmosphere of la dolce vita, cranking tunes past dinnertime. The vibe upstairs at Jimmy’s is less take-me-home-tonight; still, you never know whom you’ll meet. At L’Hostaria, bartender extraordinaire Scotty is generous with drink refills—and a cheeky matchmaker to boot. 

PATIOS
There’s no better backdrop to smiling strangers than a sunny patio—and lucky for us, there are plenty for scanning passersby. Ajax Tavern and Zeno Aspen draw fitness fanatics post–Aspen Mountain hike; the Meatball Shack, Jimmy’s Bodega, and Grey Lady on the Mill Street Mall also stay hopping after dark. HOPS Culture and Esco Patio on the shaded Hyman Mall attract a more casual constituency, as do sidewalk tables at SteakHouse No. 316, the Square Grouper, and White House Tavern on Restaurant Row. 

HOTELS
Magnets for the jet set—and locals hoping to absorb their energy—hotels make for cosmopolitan meeting grounds. Each is wildly different. Pool parties at 39 Degrees Lounge at the hip Sky Hotel turn rowdy as DJs spin past sunset. Aspen’s oldest watering hole, the J-Bar at the Hotel Jerome, attracts a motley crowd with Colorado beers on tap and sports on TV; the sophisticated Living Room Bar further inside the hotel stokes more intimate conversation. Head to the lounges at the Little Nell and the St. Regis Aspen Resort for luxury—which makes anyone look good.

PERFORMANCE VENUES
No doubt, music sets the mood. An obvious choice is Belly Up, the come-as-you-are club with cutting-edge light and sound and a cozy dance floor that turns steamy during top shows. Boasting the longest copper bar and most extensive cocktail menu in town, Justice Snow’s attracts cerebral types with Americana music and spoken-word series. The wild card: concerts in Snowmass and at the Aspen Music Festival, which attract eye candy of all ages—picnic blankets strongly suggested. 

CLUBS
Underground haunts blowing big beats are prime pick-up spots before last call. As cover charges rarely exist, there’s no shame in hitting ’em all to determine the best crowd and DJ of the night. Begin at Eric’s, mosey to Whiskey Rush, double back to Escobar, and end at Bootsy Bellows. Return to the one with the most promising prospects, and consider bottle service if you’re a baller. Oh, and don’t expect riveting conversation. Just dance.

But keep the faith… 

Then there’s the $8 million gorilla in the room. Aspen’s wealth culture touches more than just bottle service at Bootsy Bellows and memberships to the Caribou Club. It can create the perception that when armed with enough cash, anything is within reach, a sense of entitlement to the next best mate around the corner. “It was like that when I lived in Manhattan: a microcosm of the glitz and glamour we see on TV and our phones,” complains a thirty-nine-year-old doctor who spends a few weeks in Aspen every summer and winter. It’s the lure of easy access, he says: “You can always upgrade.” 

Or, as some believe, find what you need with a phone call. Hoping to help Aspenites find lasting love, thirty-year local Carole “Aspen’s Wingwoman” Gunther advertised her new matchmaking service in the classifieds. But even she was surprised to receive “a lot of calls for hookers!” from men. Even the few ladies who called in earnest “weren’t sure if it was [an ad] for a prostitute.” 

Today fifty-nine, Gunther met her former husband at the J-Bar in 1989, after sixty-two days living here. They were married in six weeks, had two children, and divorced eleven years later. Happily single since, she started matchmaking because, she says, “In a small town, it’s nice to provide somebody that extra nudge.” 

Predictably, she suggests we stay open-minded: “You may be more compatible with somebody you wouldn’t think you’re so attracted to,” she says. “Stop limiting yourself.” Gunther implores men to cultivate respect, women to make the first move, and all of us to tread slowly. “The Aspen dating scene, too often, especially with the younger kids, people just get drunk and go home with [each other]. That’s not dating. That’s reckless behavior. Don’t kiss and tell; don’t do it on the first date. Let’s bring courtship back.”

So while hooking up in Aspen can be mostly a matter of showing up, building meaningful relationships requires good old-fashioned work, like anywhere else. 

The thirty-four-year-old salesgirl sums it up like this: “Reality sets in, and the novelty wears off,” she says, having traded a footloose lifestyle for a seven-month steady. “There are a lot of really beautiful things here to be enjoyed. You can do them on your own, but when you find someone who keeps your spark alive, you make memories together. It creates a better appreciation for the town and the beauty in it when you’ve got somebody to share it with.” 

And hope to live happily ever after—single or not.

Finally, a plea from multiple men: Aspen women don’t deserve the gold-digger stereotype. “As a professionally accomplished man, it is incredibly refreshing to be surrounded by independent single women here who have no interest in taking advantage of me financially,” says a fifty-three-year-old Wall Street transplant of five years. Bad apples do exist—you’ll find them in the police blotter weekly—but for the most part, those who’ve found the Roaring Fork Valley are genuine. He looks forward to “Fourth of July in Aspen, the epitome of independence,” he says. “Where else to better celebrate liberty?” 

So, when I find myself consoling a sassy, sophisticated thirty-something friend wailing about misplaced mojo and threatening to relocate out of sheer frustration, I remind her: “Relax, it’s Aspen.” And I wink, because living in this place is its own sort of transformative romantic partnership. For better or worse, I’ve become mellower and more tolerant since moving here. My perspective on mating has shifted: I understand deep down that what I’ve found here might not be universally accepted—or even understood. Future suitors, however handsome, accomplished, and charming they may be, face a stiff rival in Aspen itself, the most worldly, experientially diverse, exhilarating small town imaginable. As it happens, I’ve been in love all along.

GREAT DATES
Whether your proclivities lean athletic, outdoorsy, or alcoholic, Aspen offers ample outings to connect with your paramour. —Michael Miracle

DINNER AND A MOVIE. A dull cliché in a town as activity-packed as Aspen? Au contraire: such normalcy can be refreshing here. If any of Aspen Film’s festivals are on the calendar (see aspenfilm.org for dates), opt for them. If not, unless you’re at opening night of a blockbuster, the Isis’s five small theaters are usually 80 percent empty, meaning you and yours will feel like you’re in a private media room. Hit the softly lit Wild Fig before or after for one of Aspen’s most underrated romantic dining experiences.

HIKE AND A MARGARITA. Smuggler is too public—you could get a text message from a prying ex, tipped off by a mutual friend, before you reach the top. Same with Aspen Mountain. So try the Woody Creek Trail. From the trailhead just past the hamlet of Lenado, it quickly becomes narrow, so there’s some forced proximity. Shaded and particularly moist for our dry climate—one of the best hikes in the valley on a hot day—it’s also a raspberry bonanza when that fruit pops. Feed them to each other on the trail, or drop them into your margaritas at the Woody Creek Tavern on the way home. 

CULTURE AND A STROLL. So many options here. Open till 6 p.m., the Aspen Art Museum will plant the seeds for an interesting dinner conversation, whether about art or architecture. Spreading out a blanket on the listening lawn outside the Benedict Music Tent is a classic, but do it on a weekday rather than at the Sunday afternoon concert, which draws locals by the hundreds. After either outing, walk the ultra-serene East of Aspen Trail through the Northstar Nature Preserve. The local bus system’s Dial-a-Ride service (970-920-9999) can get you there from Rubey Park for $1 each way. 

DRINKING AND MORE DRINKING. Inhibitions will melt away; just don’t get maudlin. If you’re up for a boozy gauntlet, start with an expertly made cocktail or two at Justice Snow’s or Chefs Club at the St. Regis, then move on to beers and the occasional shot at the Red Onion or Little Annie’s. Or you could start with an expertly made cocktail or two at Jimmy’s, then move on to beers and the occasional shot at … Jimmy’s. There’s no bar in Aspen that builds to alcohol-fueled crescendo better, especially when Jimmy himself is on hand as master of ceremonies. 

CONVERSATION AND INTIMACY. Call this one “the relationship date.” You’re no longer trying to wow your partner, just to connect. The dining room at Plato’s at the Aspen Meadows offers something atypical for Aspen: ample space between tables. Even when the restaurant is full, you feel cocooned in your experience, and executive chef Jason Thompson’s exquisite cooking remains oddly undiscovered by Aspen foodies. Post-meal, wander out onto the Aspen Institute’s grounds, lie down on the Herbert Bayer–designed Earth Mound, hold hands, and count the shooting stars. 

Take it from the Princess

ASPEN’S RESIDENT CARRIE BRADSHAW OFFERS LESSONS FROM HER DATING PAST.

I wouldn’t exactly call what I did in my thirties “dating,” but for over a decade I documented the roller coaster that was my single life in the Aspen Times in my weekly column, “The Aspen Princess.” Take it from me: even though “the odds are good but the goods are odd”—yep, they were saying that when I first started dating here, too—you can still find your diamond in the rough. Here’s some wisdom I wish I could have shared with my younger self. —Alison Berkley Margo

AVOID FIXER-UPPERS
You know the old expression, “If it’s not broken, don’t try to fix it”? In Aspen, the opposite is true. If he’s broken, you’re not going to be able to fix him. Aspen is an enabling town, and if he needs rehab/loves his bong more than he loves you/cheats/lies/sleeps around/has major mommy issues, chances are he always will. You can move on, because his next girlfriend will be the first to tell you he never did. 

ANALYSIS TO PARALYSIS
Men aren’t complicated creatures. If his phone is going straight to voicemail, it’s because he’s out skiing and partying with the boys and doesn’t want to talk to you. When you’re in a good relationship, you’re just in it, not talking about it. If you find yourself turning to your friends with your questions about him, chances are you already have your answer.

TIMING IS EVERYTHING
True story: My husband worked as a bartender at McStorlie’s and Texas Reds, two now-defunct Aspen dive bars I frequented often. Chances are better than good that he served me more times than I care to count. So why didn’t we notice each other then? Were we just too drunk or distracted by the wrong people, entangled in our own mistakes? Which brings me to my next point.

JUST WHEN YOU THINK YOU’VE MET EVERYONE…
I was almost thirty-nine and had recently been dumped by a fixer-upper. It was New Year’s Eve. I’d hit rock bottom. I went skiing with some girlfriends and planned to go home right after après-ski to take a Xanax and go to bed. I walked into 39 Degrees at the Sky Hotel, and a guy I’ve never seen before grabs my fur boot and pretends it’s attacking him. He wrestles my leg to the ground like a wild animal in a not-so-subtle move as a group of mutual friends sat, mouths agape, to witness the spectacle of what was unquestionably love at first sight. All of our friends seem to know each other, and we’d both lived in Aspen for over ten years. So how was it we’d never met? Right from the start, Ryan made his intentions crystal-clear. For all the times I’d been wronged, it was obvious to everyone that I’d finally found Mr. Right.

HAPPY ENDINGS EXIST, EVEN IN ASPEN
Two years later, when our wedding was given a two-page article in the Vows section of the New York Times, Ryan was as transparent as when we first met. He described his single years in Aspen: “I burned through ladies like I was spinning CDs.” He also said he’d been humbled after his divorce and that he, too, feared being older and alone. “I didn’t want to be the fifty-year-old guy going to a bar looking for a twenty-five-year-old woman,” he said. “You’re lonely. You look lonely.”

I think everyone in Aspen has a tendency to look for love in all the wrong places—until one day, fate leads you right to him, that one person who was probably always there, waiting for you all along. It may take a while, but it’s totally worth the wait.