Jen Responds: Her side of the blind date setup - Ski Mag

Jen Responds: Her side of the blind date setup

When Skiing magazine set two readers up on a blind ski date, the potential for disaster was high. Luckily, a shot ski and a first-run yard sale helped break the ice. Here is Jen's response to the weekend she spent with Wes at Sugarloaf, Maine.
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Jen and Wes

After reading the impressive play-by-play from Wes, I am only hoping that my own mind will play out as an acceptable virtual memory of sorts so I can share my side of this spectacle. No, I did not keep a running dialogue of our weekend together, but I do remember enough in between the drinking and skiing that it all did happen the way he describes it. It was nice to meet someone as happy and lively as Wes, and I definitely am glad that I chose someone as appreciative as he. We had a great weekend together, skied a ton, laughed a ton, and imbibed a ton as well (or at least I did). We were lucky enough to have a beautiful spring-like day, bluebird skies and great spring snow conditions, although quite variable.

I chose Wes out of all of the entries because he seemed to be the most excited about the whole idea. His letter was fun, lighthearted, and full of energy, so I assumed he would be too. He had never skied out East, so I thought it would be a great opportunity to have him make his own judgments towards New England skiing.

When I walked into the hotel’s bar to meet Wes on Friday night, I was greeted with a great big smile. He seemed very nice, talkative, and quirky (just like his letter) right off the bat. We chatted small talk and seemed to get along pretty well. I thought to myself that this wasn’t going to be as scary and awkward as I had anticipated. After a couple of beers and some casual exchange of words, we brought my cousin to her surprise 15th birthday party. We hung out with the fam for a bit, and then decided to go down to The Rack (a local favorite, and always a good time).

I remember telling Wes that I wasn’t going to drink any liquor that night because I knew I needed to be fully alert and ready to rip all day. Needless to say, the plan was totally averted once we left the condo. The night was filled with whiskey, tequila, PBR, and whatever was in that shot-ski pic. Friday night was a blast, and I think Wes had fun, too.

I woke up Saturday morning as ready as can be, remember, I said no liquor. With the hangover emanating around me I finally got to the Super Quad where we met, both ready to scope out each other’s skills. Now, I am totally all about first impressions, but ironically, I’m usually the one making a total fool of myself when I meet people. I’m pretty sure I did that on our very first chairlift ride. A ski patrolman who I thought was going to take the chair ahead of us decided at the last second to let us go, which totally confused me. I looked up to see Wes riding up with two other people while I was still standing at the gate. I had to take the very first lift together all alone, looking like a total Joey. Typical hungover Jen behavior let me tell you. So when I finally made it to the top, we started down our first run when all of a sudden, I feel my head slamming off of mogul after mogul, total yard sale all over the place. Talk about those variable New England conditions! Needless to say, once I was done tumbling down at Mach 10, Wes came skiing behind me laughing and gathering my gear (I’m sure he asked if I was okay, but he was laughing hysterically at me). Nice guy.
The rest of our day ended up being tumble free and pretty smooth. We skied, hung out with my friends at Bullwinkle’s and Widowmaker’s deck, and just enjoyed each other’s company. Saturday night was just as Wes described it. We started out watching tv, and ended the night with more drinks, dancing, and partying into the early AM hours.


Sunday we only ended up taking a couple of runs because I had to head back to reality early afternoon. However, I can agree with Wes that he did do a great job keeping up on his rented alpine gear. I was impressed. Everyone was really nice and generous towards us the whole weekend, and I’m glad that Wes got to meet a lot of my local buds. As far as being the queen of Sugarloaf, I wouldn’t go that far (I’m pretty sure you have to earn that title). Yes, Sugarloaf is no Alta, but it’s my favorite place to spend my weekends in the winter.

Overall, I’d say the date went very well. I’m pretty sure I entertained Wes with my usual antics, and that he had a great time. As far as a torrid love affair goes, I don’t really see that happening, but I did get an opportunity to meet a very nice, thoughtful (he mailed me a package with a cute hat from his bud’s company and a miniature orange cone--long story), and high-spirited guy. I didn’t meet my soul-mate, but I am very thankful that I was given this opportunity this winter, as I met many supportive people, and received many entertaining letters from a bunch of great guys that love skiing just as much as I do. I want to say thank you to Megan, Skiing Magazine, and Sugarloaf for creating this contest for me and for making it all happen. I love skiing more than anything, and I only hope that some day I will get to share this passion with someone who loves it just as much as I do. So as they say, let the search continue…

—Jen Winslow

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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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