Sean Beckwith: Valentine’s Day and Aspen’s cutthroat dating scene |

Sean Beckwith: Valentine’s Day and Aspen’s cutthroat dating scene

Here’s your friendly reminder that Valentine’s Day is coming up. Get your dinner plans and flowers in order for a night of romance. If you’re single like myself, grab a bottle of bourbon, get that “Mad Men” queued up, turn off your phone and prepare to wallow in loneliness. For those of you who can’t understand my level of morbidity on the holiday of love, maybe try for some uplifting haikus.

This column is for the single fellas and ladies who know how frustrating the Aspen dating scene is. Now I’m not going to sit here and lament about exes or regrets — that’s for your diary. However, let’s look at the ins, outs and what-have-yous of finding a lady or guy friend in this wonderful place.


Some people don’t have these same dating issues because they’re gorgeous. We all know of these cases in which a guy or girl seamlessly goes from one relationship to the next. There’s nothing wrong with that. But for those average-looking folks, things are a little more complicated.

To be honest, most Americans are probably behind the Aspen fitness curve considering Pitkin County’s perennially high rank among U.S. counties. Scaling a mountain with a full 40-liter backpack sounds like an entertaining training montage from “Kung Fu Panda” and not how I want to spend my weekend mornings. I prefer to start my days off with a bagel sandwich and a bloody. If I were to describe myself, I’d say a skinny Jonah Hill or a fat Chris Pratt depending on how full your glass is. For some of us, working out isn’t a top priority. I’m not (that much of) a fat kid (anymore).

However, even if I was shredded, my odds would still be stiff. Pitkin County is no Summit County when it comes to an unfavorable ratio, but there are a lot of dudes, which sounds like a good thing for the ladies. But when you consider how over competitive and, frankly, desperate large swarms of guys can become, I’m sure it can be overwhelming.

If you want a litmus test, next time a new girl starts at your job, just observe how many pointless stops guys make at her workstation. We get it Larry, you have the funniest memes; now get off Instagram and go back to work.


Aspen is cutthroat when it comes to dating. I’ve personally and unknowingly introduced both of my sisters to their current sweethearts. One of them is even engaged. Be careful of that though because dating your friend’s sister elicits only two responses: “Dude, really? Are you serious?” and “Are you f—ing kidding me?” He’s never going to say, “Oh, that’s great. Just fantastic news. When can we hang out in this awkward situation again?”

As mentioned above, you could try to find someone at work. It’s perfectly normal in certain workplaces like restaurants. In a professional office setting though, it’s not ideal. You may think it’ll play out like a story arc on “The Office,” but in reality it will probably be awkward and uncomfortable.

You could go to the bars, throw game at a wall and see what sticks. I’ve done that; it usually turns into me throwing drinks back and wondering why I thought overly loud music and getting plastered would exhibit my charm.

Another route is Tinder or Bumble or whatever app you repeatedly delete and download out of frustration. Getting a date on Tinder isn’t that hard actually. Getting a second date is the tricky part, which is totally understandable considering I spend more creative energy in opening Tinder conversations than I did on most essays in college. (I don’t know why I don’t stay with lines that work but something about reusing pickup lines strikes me as lazy. And when it comes to lazy writing, that’s where I draw the line.)

The most normal option — even if swiping on your phone is increasingly becoming the new normal — would be to hope you’re lucky enough to meet someone through friends. This would be my preferred option. But when a lot of your friends are single, they’re not likely to dole out leads, and who could blame them? Even if you do get them to talk, be prepared to hear some things you may not want to because it’s a small town full of Eskimo brothers and sisters.

Anyway, if you do have a date for Valentine’s Day, I hope it’s someone you really enjoy being around. And if you are alone, it’s not a big deal. Be vigilant. Don’t stop trying. Have confidence in yourself. Everyone has a type, and you never know who is interested until you try.

Sean Beckwith is a copy editor at The Aspen Times. He can be reached at


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