Writing Switch: Just the tips for dating in Aspen | AspenTimes.com

Writing Switch: Just the tips for dating in Aspen

Benjamin Welch and Sean Beckwith
Writing Switch

Life and love in Aspen can be hard, especially when some days you pass the mirror and say “Oh yeah, I’ll definitely fit back into 32s soon” and other times you’ll catch a glimpse of yourself and think “Am I pregnant?”

We didn’t want to give away all our advice for free here, so for these tips we prepped by making tasteless sexual jokes to Sean’s roommate, Dangerous. You know we’re desperate for content when we’re trying to make each other horny.

“I got a golden mushroom for you,” Sean said while playing “Mario Party” (Ben won because he’s a Nintendo OG). “You’re my Boo!” Ben cheered as a beady line of coins was extracted from the rear of the ghost character.

If you’re struggling to get a date this Valentine’s Day, there’s a right and wrong way to make those 4 inches ski like 8. It just depends on who you trust more.


• Wrong

SB: Seriously, there are plenty of terrible approaches to picking up ladies other than sepia-filtered phallus photos, but we’ll focus on a couple of Aspen-centric missteps.

One such poorly thought-out method is what I like to call the “Over-apres, under-ski.” Yes, skiing can be used as an excuse to get day drunk but so can any other weekend activity be it golf, pool day, Sunday fun day, football, etc. Slurring your perceived game at 3:30 in the afternoon will do the opposite of your intention and most likely leave you sleeping on the 4:15 shuttle than filthy shuffling on the dance floor with a shorty.

This is more of a summer flex — if you want to call it that — than winter. The Aspen area has miles upon miles of trails. You can literally get lost on them, but somehow a segment of guys can’t seem to find them. Rather than enjoying the pristine solitude of a secluded path, they’re doing their best Dennis Reynolds impression and popping off their shirts for a jog around Aspen’s core. I don’t see a lot of ladies doing this and that’s probably because they don’t want to be hit on.

Bro, guys don’t complain about catcalls because it doesn’t happen to them. No one wants the first impression of their boyfriend to be that of a sweaty dude and his gross armpits. Get lost, preferably on one of the trails not named Hyman Avenue.

Also, try not to date your co-worker’s sister.

• Right

BW: Most cliches don’t apply when you’re actually trying to meet people. “Just be yourself.” Yeah, unless you suck, then you gotta be someone else. “Stay off the apps.” Well, maybe, but how else are you going to get laid without having to overcome the social anxiety of chatting up strangers? At least when you match you can infer that they’re somewhat attracted to you, and that’s the hardest quotient to determine in any amorous scenario. Despite what my profile pic suggests, I’m not actually an extremely handsome guy, so if I can do it, anyone can.

Don’t take rejection personally. You want real confirmation you’re only attractive to 1 to 5 percent of the female population? Sign up for Tinder. Bumble loves Aspen because its matriarch has a house here (she hasn’t swiped right on me yet, but Whitney if you wanna witness a well-crafted routine hit me up with that “heyyyyy”), though if you’re an average-looking guy (and be honest with yourself) you’re already an underdog because not only do you have to hope for the miracle of a match, she subsequently has to initiate the conversation. Personally, I’m crippled if you take away my mirthful GIF openers, but I guess if there was an app that automatically blocked all the bots and chicks with Machu Picchu photos, I’d sign up for that, too.

Anyway, if that doesn’t work, just date your co-worker’s sister.


• Wrong

SB: For locals, Aspen is unrelentingly casual. Upscale attire is your best flannel, jeans and maybe a pair of boots that haven’t been wrecked to s— yet. Showing up in Italian loafers and a blazer like you just got off a PJ from New York will get you roundly mocked on her girlfriends’ group text.

“Yeah, he showed up looking like a guy who’d come up to the front desk and ask me ‘Where’s the party at tonight?’”

Another thing not to do is let the environment dictate to you. If she wants to go to the now-defunct Whiskey Rush for a few drinks after dinner, that doesn’t mean she wants to re-enact your last escapade at the nightclub once notorious for its alcohol-induced, head-splittingly bad decisions. Maybe she has a friend who works there and wants to get her impression of you before committing to a second date. After all, it was, excuse me, is a Wednesday night.

• Right

BW: Don’t spend all day texting her about your job woes and looking for the perfect opportunity to accidentally schedule a date. Despite being addicted to our phones, millenials actually abhor the commitment of responding to messages, so move to an in-person arrangement ASAP. It’s also harder as an adult to plan activities that aren’t just drinking at a bar and outwitting every random Trevor and Cayden who tries to mack on your partner. Take a walk through the Ute Cemetery at night. Climb up basket-shaped museums downtown. See how fast you can pull open the door at Zane’s. Stand in galleries while fighting the guilt of knowing you’ll never buy anything.

Keep the conversation casual. It doesn’t matter what you say, as long as you’re saying something. Bonus points if you can work in orangutans and re-enact your vision of what an Aspen strip club would look like.


• Wrong

BW: “Are you sure those are long enough?” I asked my date as the rental guy handed over a pair of 143s. She had spent hours at Grey Lady the night before telling me about all the techniques she had learned in her ski lesson at Vail, and how she had to come back to Colorado for the “Aspen Extreme” experience now that she was a capable skier.

Her eyes widened. “That’s a little bigger than I’m used to.” I’ve heard that before. Uh oh.

I soured when a pair of elderly passengers boarded our Elk Camp Gondola bucket and loudly discussed their recently deceased mutual friends. While I rolled my eyes, my companion threw a couple of names out. I guess when you go out with cougars reality sometimes comes crashing back at you unexpectedly.

I advanced about halfway down Funnel and glanced up. She looked like Elmer Fudd trying to stay upright on a frozen pond. By the third turn she caught an edge and wiped out. Before this, the last time I had seen a woman over 40 cry was when my aunt realized I had blocked her on Facebook. Sorry, Jenny, my comedy loses its luster when all the relatives start commenting “YUM1” on my album of breadless corndog pics.

After sliding down the incline on her butt for 30 minutes, we rolled into a restaurant at the mall. The waiter tried to impress her by making guacamole at the table, but it, um, accidentally got knocked over (Pro tip: Guys, don’t stand for it when the waiter hits on your date; I’m tired of having to play along and then tip you 20 percent).

Jeraldine tried to kiss me straight on the lips when she got off at her stop, but since I have a reputation to keep and know too many people on the bus route, I deftly turned the other cheek.

She was hospitalized for altitude sickness the next day and despite all the Spotify playlists she sent me, I could never muster another conversation with her. The end.

• Right

SB: I’ve never actually dated a girl who skis during my eight years in Aspen, which is probably an indictment of my personal life more than anything but that’s neither here nor there. The best ski date is one who can and actually does keep up. This goes for both genders. Ripping powder runs or groomers all day before a healthy après and hot tub is fun with just about anyone. So, I imagine it’s probably doubly enjoyable when it’s with your romantic interest.


• Wrong

BW: Nothing breeds animosity faster than staying in an Airbnb studio and being paralyzed with the fear that you can’t poop in privacy. It doesn’t help being on the receiving end of judgmental eyes as you crack the 8:30 a.m. PBR. When I take a trip, aka anywhere past the roundabout, I don’t want to spend time in stores or at attractions, I want to see what their bars are like. The perfect vacation is when I do the exact thing I would be doing at home: slumped over a stool and refreshing Facebook and Super Smash Bros. threads on Reddit.

This is probably why I almost always travel alone.

• Right

SB: This one is easy: Anywhere that’s not your subsidized, roommate-infested apartment. Even booking a room at the Limelight or, if you have the connections, The Little Nell for an overnight is enough to have both of you feeling refreshed. Waking up to a mountain view that’s not accompanied by the morning groan of your roommate might be just enough to convince you that you, too, are on vacation.

A couple who are friends of mine have been taking advantage of the Avalanche Ranch hot springs, which are better than the hot springs off the highway teeming with pervs and naked people who shouldn’t be naked in public. So, if you need a place in the valley for a retreat because you’re tethered to your job like most of us, remember we live in a top-notch destination suitable for any intimate excursion.

Win a night out with both Ben and Sean and listen to them bicker over which wing flavor goes best with ranch dressing. Raffle tickets are $100. bwelch@aspentimes.com sbeckwith@aspentimes.com