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Chasing Jen: Skiing Mag's Blind Date Setup

In Skiing magazine’s February 2009 issue, we ran a letter from Jen Winslow from Maine, who asked for our help finding her a guy who cares about skiing as much as she does. So we sent out a call for help, asking guys to write in and tell us why they deserved a ski date with Jen. Sugarloaf was willing to donate some lift tickets and an apres-ski bar tab for the occasion. Dozens of eligible bachelors from all over the country wrote in, hoping for their chance at romance. The lucky guy? Wes Berkshire, from Colorado, who flew across the country to meet Jen. Here’s Wes' story.

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Jen’s Letter:

Dear Skiing Magazine,
I have been struggling for the past five years since moving back home to Maine from Colorado, where I went to CU and skied Summit Country three days a week each ski season. I’ve been trying to find what I want in life, what job I want, where I want to live, how I’m going to pay the bills, if I’m going to meet a man who meets the requirements on my list, and most importantly, how I’m going to incorporate skiing into this amalgamation I call my life.
I have had my share of relationship drama—the one who taught me all I know about skiing (until I left him in Colorado and was then able to learn more and more on my own—thanks, Nick), the crazy drug-addicted ex, the time when I had to pull my life back together (when I became the best skier I have ever been—thanks, Matt squared), and then the latest relationship, the one I knew was destined to fail because he told me after three knee surgeries, he decided he’d never ski again. Well, that just wouldn’t work now would it? So, here I am again, single and waiting to find my soul-mate, a man who wants to go to the Loaf every weekend, hang out with my friends, and rip it up until cocktail time.
Skiing is the only constant that I’ve had in my life since the fifth grade. It’s my ultimate passion, and it only gets better and better each year. We had an amazing season last year (for New England), lots and lots of snow, and a new company that really stepped it up. So, if you see my ripping if up at Sugarloaf this season, don’t be afraid to talk to me. Just be afraid to ski with me.

Jen Winslow
Windham, ME

The winner’s letter to Jen:

Hey Jen-

I have to say, everything else aside, just throwing down the gauntlet like you’ve done here is a pretty awesome move. Oh, and daring anyone to keep up, utterly bad ass, well played. Girls with a passion for skiing are entirely too few and far between. I guess I could launch into some sappy cliché about how such a beautiful girl shouldn’t have any problem finding a cool guy, but then I lived in Tahoe for eight years and I’m well aware of the staggering male population of drunken douchebaggery that I’m fairly certain exists anywhere near a ski hill, so I understand.

 So…about me…well, I’m a leo, I enjoy cheap poetry and long walks on the beach…no wait, hang on. I’m a telemarker, I blame my parents. I went to this really amazing university in Boulder, you may have heard of it. Go Buffs. Seriously, where else could you look out the snowy window of an 8 am class, decide to bag the lecture and be making turns by 9? I spent eight years living the dream and skiing my face off in Tahoe and now I’m back in Boulder, for the time being anyway, skiing mostly at A-Basin and Breck.

I’ve never really skied back east. I think I’ve skied just about everywhere else, but not back east. I know, I know, I’ll take my shaming. When you grow up out west you get used to people from out east coming west to ski, not the other way around. So I want to switch it up, I want to come east, I want to know how salmon feel. So please (this is the part where I’m down on my knees begging, pathetic I know) let me come ski back east, let’s hang out and make some turns, it’ll be fun, as long as you can keep up.


Wes’ recap of the ski date

Denver International Airport, CO
12:17 A.M.

I’m not sure I’ve ever actually been at an airport at this time of night. It’s kind of weird, the whole place is dead except for a roaming crew of janitors and some sleepers. My flight leaves at 1 A.M, yeah, seriously. It’s been an odd day. Denver finally got that winter storm we’ve been waiting for. Perfect that it comes on the day I’m leaving town. It’s left me an odd mix of tired, excited, and anxious.

Gotta say I’m a little sad too. Shane McConkey died today and as a skier that’s not the kind of thing you take lightly. The guy was a legend and from all accounts a good stand up guy. That’s a rare thing.

So all of the Front Range has been a complete disaster all day. You see, people in Colorado, Denver especially, don’t deal with weather too well. I guess it’s bound to happen somewhere that’s sunny and beautiful 320 days a year. At any rate, the roads have been a nightmare. It’s a combination of bad weather, a population that for the most part can’t drive any better than Britney Spears (or her kid), and a crew of plow drivers that you’d swear have never seen snow before. At any rate, a bunch of flights have been cancelled all day (Southwest cancelled every flight into and out of Denver) but my airline, Jet Blue, has been on time and rockin’ all day. Luck of the draw I guess. So here I sit, waiting for my 1am departure. Can’t say I’m exactly psyched to be flying out of an airport in the middle of a blizzard. But compared to not getting out at all, I’m practically doing naked cartwheels down the concourse.

JFK Airport, NYC
8:39 A.M.

Yawn. Somehow made it out of that Denver blizzard last night. I think Jet Blue was the only airline getting anything in and out of Denver with any consistency yesterday. Pretty sure I’m the only person hauling a pair of tele boots through JFK right now. All kinds of uber-fashionistas, very serious business-folk, and extended families, but no tele boots. They’ve been boarding this flight to Long Beach at the gate next to where I’m parked here for about two hours now. I swear most of the passengers could have taken the Greyhound there by now. I wonder how the leg room compares?

While I’m a little tired, it’s nothing a good cup of coffee won’t fix. JFK is reminding me that airports, some more than others, provide some of the best and most hilarious people-watching I’ve ever seen. Are they really pumping the soundtrack to West Side Story through an airport in New York City right now? Yes. Yes they are. “Blah blah blah blah in Amereeca! Blah blah blah blah in Amereeca!” Oh man, it really doesn’t get much better than this. I was thinking that JFK was going to rival Reno as far as pure insanity of experience goes, but this might even top the Biggest Little City in the World.

I’ve seen more Hasidic Jews in the last hour than I’ve seen in the past 31 years combined. Crazy. Between that and the West Side Story montage all I need is a few fat mobsters to waddle through and I’ll have the full trifecta. Oh, did I mention the Cuban window cleaner openly singing, with some good volume and projection (this concourse must have been designed for acoustics) while soaping up the glass? Like I said, this place is awesome.

My flight from Denver was about as good a flight as you could ask for. I got a whole row to myself so I was able to stretch across three seats and saw logs for the better part of the flight. I’m fairly sure I even slept through the complimentary morning beverage and warm towel service they promised as we left the tarmac in Denver. Oh well.

They’re still loading those poor people going to Long Beach, maybe everyone is being flown there one at a time. At least they could say they were getting something for those extra bag fees. Some lady (she had crazy coming off her like Ann Coulter) just charged through a closed door down a jetway setting off an alarm that went for a good two minutes before they could drag her back just short of kicking and screaming. And just what were they so upset about? Oh, she had a couple of iced coffees she apparently wasn’t supposed to have. Nevermind that the door, jetway, and flight were all closed. Apparently that’s no big deal. I honestly thought I was going to watch her roll right off the end of the jetway and onto the tarmac a la Dumb and Dumber. What happened to airport security? Shouldn’t a bunch of big-ass dudes in black coats beat her into a wet spot on the carpet before dragging what was left of her off to that hidden place where they destroy unattended baggage?

Off for Portland in about 90 minutes. The sign at my gate just says “Portland.” Not Portland, Maine, or Portland, Oregon, or Portland, Uzbekistan. Makes me wonder if flights from San Francisco to Portland, Oregon, just say Portland or if they make the distinction. I need to go find a steady source of caffeine if I’m gonna keep this show up and running. Some lady of Hispanic heritage (I’m going with Puerto Rico or Cuba, but only because I’m on the East Coast) is about to beat her otherwise hyperactive kid like Kobe and OJ beat the criminal justice system. The kid in question is running around in blue surgical gloves carrying a plastic bag full of something I can’t identify. Best. Airport. Ever.

Sugarloaf Mountain Hotel, Maine
4:37 P.M.

I’m here! Yeah! I love big simple mountains, not a lot of sprawl across three or four peaks (talkin’ to you, Breck), just a big mountain and some good runs and Sugarloaf appears to be exactly that. If I could get the window to my room open I could hit the base lodge with a rock. They gave me two three-day tickets; would it be wrong if I sold the other one? I mean, why not, right? Anyway, the sun’s out and I’m stoked. Should be a good few days.

The weather is supposed to be good tomorrow, Sunday…maybe not so much. But we’ll see. I was pretty tired when I got here so I had a nice little nap. Jen was a bit slower getting on the road. That’s not to be judgmental, I really have no idea what she was up to today, if she was working or how much or what. At any rate, it actually worked out because it gave me a little time to settle in and get my bearings and feet properly on the ground.

Now it’s a matter of whether it’s going to be an evening of swilling PBR and shots, stumbling in at some unholy hour of the morning, or just a mellow cocktail or two. Either way I think I’ve pretty well committed to having a vodka Red Bull at some point in honor of the late great Mr. McConkey, so maybe that’s your answer right there.

Black Diamond Steak House, ME
5:10 P.M.

First encounter. Really, honestly, truly, I wasn’t nervous. I mean, what was I going to do but be myself and have fun, right? Jen is coordinating a surprise party for her cousin so we met for a couple pre-game drinks. Me: Stella, Her: Guinness. Sounds like complete opposite ends of the spectrum I know, but I’m a big fan of both so I was kinda smiling about it.

Anyways, I got there first. I like to be early and post up at the bar. Not that I had some game plan or premeditated operation, that’s not it, just for my own paranoia I like being there first. Maybe I just like to get a little booze in me first (which I’m pretty sure is one of the signs of alcoholism, but this was a couple sips, not 4 or 5 shots, so get off me). She was immediately recognizable and immediately beautiful and we immediately got on talking about all the things that any skier, or CU alum, talks about. Bottom line: it went well, we had a couple drinks, a few laughs…Did I mention how glad I am not to be in Boulder bored to tears? Good.

So here we go, surprise birthday party for a 15 year-old and a bunch of her 15 year-old friends. Is that a weird way to spend an evening with someone you’ve just met? Probably, but whatever. I’m told there will be adult beverages afterwards, so it’s all good.

Sugarloaf, ME
8:03 A.M.

Some hazy thoughts and memories from last night:
– Old people at Sugarloaf don’t mess around. There were as many people my parent’s age getting down last night as there were my age.
– I think I met Steve Martin at some point, he said his name was Rod but I knew he was just trying to keep things under the radar.
– I was promised a face to face with Geraldo Rivera but sadly it never materialized. I really wanted to ask him about Jimmy Hoffa’s tomb.
– Jack Daniels was not supposed to be involved.
– Jack Daniels was involved.
– So was tequila.

Sugarloaf, ME
8:00 P.M.

Whew. What a day. Okay, first and foremost. Jen rips. Period. She skis as fast as anyone I’ve ever known. I’m fairly certain now that the term “Figure 11’s” was coined after watching Jen ski.No one keeps up, they just chase. I could not be more happy or impressed.

Oh, and she’s the queen of Sugarloaf. Seriously, they should get her a crown. She knows everyone, it’s amazing. So, by association, I was a local celebrity too – pretty awesome. We actually had a lift op ask her when her big date thing was. I started laughing and she just kinda pointed at me. Classic.

It was a great sunny day all over the mountain. Beers on Bullwinkle’s deck in the afternoon sun was about as good as it gets. Thick memories of the Ice Bar in Tahoe. Great après at the base area too. There’s such a cool, friendly community at Sugarloaf. Everyone knows each other (or at least they know Jen), they’re all super friendly, and when the weather’s nice, they’re all hanging out outside having a post-ski bevvie or two and soaking it in.

We hit the infamous Bag for dinner. Bag burgers are something of an international phenomenon (at least in wise ski circles) and for good reason, easily the best burger I’ve had in a hell of a long time. Believe the hype. So now I’m back at the hotel for a quick shower and then it’s out and about for a little Sugarloaf nightlife.

Sugarloaf, ME
9:00 A.M.

You know the kind of night that seems like it’s going to be mellow (not bad, just mellow) and then goes completely bonkers? I love those nights, and that was last night all the way. We went from watching Hugh Hefner’s ex on some travel channel beach show at Jen’s condo to drinking out of random 12-packs upstairs at Widowmaker’s late night.

In between, we caught a good, Grateful Dead-heavy band at the bottom of the access road. Widowmaker’s is THE bar around here. It’s the Mangy Moose, the Eldo, or the Pete and Peter’s of Sugarloaf. So last night, when they closed – because as I mentioned before, Jen is beloved local celebrity numero uno – we hung out upstairs in the loft above the bar drinking beer. I rolled back to the hotel around 3A.M. I’m a little tired this morning, but nothing that a little coffee and skiing won’t fix.

Sugarloaf, ME
9:16 P.M.

Disaster narrowly averted. As I was yawning a bit and putting my skis on this morning, one of the cables on my tele bindings busted. Needless to say, I was not a happy camper. So, being positive and proactive and refusing to let it bum out my whole day, I dumped the tele gear and rented some downhill skis and actually had a really good time skiing downhill for the day. I tried to drop my knee a couple times and nearly died but beyond that it was all good. It was actually easier to keep up with Jen on downhill skis. I think I might ski on downhill gear more if I skied with her more frequently. It’s just easier and a fun change.

Jen had to leave around 1 P.M., work work work. I was sad to see her leave. The forecast today called for a 90% chance of rain. All morning it was nice and dry as can be. About 30 minutes after Jen left…pouring buckets. How’s that song go? Ain’t no sunshine when she’s gone? I’m not trying to get all sappy here or suggest the presence of some kind of super-natural weather gods or anything…I’m just sayin’.

I skied a bit longer and came in soaking wet, but stoked. Had a good nap, and now I’m staying in tonight. I’m pretty wiped out from the weekend. A pizza and some Family Guy will just about do it tonight.

I had a great time. Jen is truly one of a kind. You know people that are just so full of life, they’re just drinking it down in big massive gulps between laughs and smiles? That’s Jen. She’s amazing, and after the last couple days, I am indeed quite smitten with the beautiful Ms. Winslow. She is an outright celebrity at Sugarloaf. She knows everyone and they all know and love her. Queen of the Mountain, Sugarloaf edition: That’s Jen for the win every time. Sugarloaf isn’t the sickest, craziest mountain out there, but it’s still pretty good, and what it lacks in gnar, it makes for in spades with character and fun. Hope and can’t wait to be back.

Portland International Jetport, ME
1:31 P.M.

Back at PWM. Super sad to leave. I mean, not sobbing like a kid with a skinned knee sad, just kind of melancholy, like I don’t want to go. I’d rather stay. It’s been an amazing weekend all around and that’s obviously the impetus here. I sincerely hope this isn’t the last time I come through this airport or the last time I hang out with the inexplicably awesome Jen Winslow. Time will tell.

Got on an earlier flight, sort of. I got on an earlier flight to JFK but still the same flight from JFK to Denver (it’s the only flight from JFK to Denver actually) so the only real difference is that I sit at JFK for a few hours instead of Portland. Honestly I’d like to stay in Portland just for the sake of not leaving Maine for a few more hours. But then again, JFK is still the most entertaining airport I’ve ever seen so I can’t complain. The gate agent here in Portland is clearly of Irish descent, and he’s hysterical. “Ladies and gentlemen, you may have noticed your chariot has just arrived…” How can you not smile at that? The guy deserves a high-five and he may just get it on my way down the jetway. I suddenly have a thirst for a Guinness. Is that weird?

JFK Airport, NYC
8:14 P.M.

JFK continues to impress on all levels. It’s not as funny and WTF-ish this time around but then I’ve had my head buried in my laptop most of the time, so there’s a very real chance I’ve just missed a lot. I did sit next to the gate for a couple flights to Puerto Rico for awhile. Didn’t hear a word of English for like an hour. It was like going on a whole other vacation without ever leaving the airport. Just had possibly the best Pad Thai I’ve ever had. Yeah, at an airport too, I know. The Jet Blue terminal at JFK has this killer modern food court-ish thing that has a virtual European market full of different foods and options, all done up properly and good. Not just the standard assortment of frozen and microwaved shit on a shingle. Big ups to the fine folks at JFK. Back to Denver here in about 30 minutes. Wah! Don’t wanna go!