Hiking Date

—Sunday, March 25, 2012—

Holy God, this was the earliest date ever.

IMG_1928My first alarm went off at 5:30 a.m. but it wasn’t until 5:47 a.m. that I was finally “awake”. I dragged myself out of bed and into the shower to get ready for a splendid day of hiking with Bobbie, who I knew would definitely be on time and totally have her shit together.

I got dressed in the only clothing I had which seemed suitable for hiking. Chino shorts, cross trainers, 3/4 length t-shirt, light rain jacket and a hiking pack for water, snacks and additional supplies.

The day’s ‘Fitness Hike’ was made possible thanks to the fine folks at Brooklyn Outfitters (who have since been acquired by Discover Outdoors), as they were kind enough to not only organize the whole thing, but also waive the fees for Bobbie and I, all in the name of OHD. My friend from college, Katie, was the connection there, and she was gracious enough to put me in contact with the folks in charge. [I can say honestly though, that all the good words that will be said about them are genuine and not motivated by their sponsorship.]

Thanks to Brooklyn Outfitters (BKO), we had guidelines as to what to pack and how to prepare for the day ahead. They had sent us an email the day before with some information and advice.


Hello Hikers, 

We are excited to bring you into the wilderness tomorrow!  Below you will find some last minute information.  If you have signed up for more than one person, please make sure they have received this email.


7:30am from Manhattan Location – (SE Corner of 36th and Park)

7:45 am from Brooklyn Location- (N 6th and Driggs Ave)

If you are running late, it is important to call us at [555.555.5555].  We do not like leaving anyone behind!! 

Return (approximate)


Showers likely, mainly before 8am. Cloudy, with a high near 64. Northeast wind between 3 and 6 mph. Chance of precipitation is 60%. New rainfall amounts of less than a tenth of an inch possible. 

Bring a rain jacket just in case!


You will burn a lot of calories throughout the day.  Be sure to have a big healthy breakfast and start hydrating as soon as you wake up.  We will make a stop before the hike to get any last minute provisions.  Bring at least 3.0L of water!! 

Hiking boots or trail shoes are highly recommended for this hike.  If you do not have them, trail shoes or running shoes are recommended.  

Avoid cotton clothing.  Synthetics and animal fibers are best for wicking away sweat from the skin.  Dress in layers and be sure to bring a hat. 

Pack a lunch that is high in energy! 

If you have any further questions please visit our FAQ’s page, email or call us at [555.555.5555].

Happy Hiking!

The BKO Team


I began hydrating (very important to a good date) as soon as I woke up and I also made a couple fluffernutters to bring with me for food (Has no one made that the name of a weird sex thing yet?).

Although Bobbie and I had had some discussion about coordinating snacks to bring along, I mostly went off-script the night before and bought a bunch of useless food. I had Luna bars, Cliff bars, coffee cakes, mixed nuts — which would have likely been enough — but then I added some other junk as well. Two 1.5 liter bottles of water were packed along with sanitizing wipes and an extra layer, and I was pretty sure that I had everything I needed.

Bobbie and I met each other at 36th and Park around 7:20 a.m. and as the forecast had predicted, it was gray and precipitating ever so slightly. Though it was a bit chilly for shorts at that early hour, I knew it would warm up throughout the day. Plus, we’d be spending the first portion of our day in a van, driving to our destination: Harriman-Bear Mountain State Park.

Normally, I would have felt bad dragging a date out of bed so early in the morning, on a less than beautiful day, to spends hours with me traveling and hiking. Luckily, I really didn’t have to worry about that with Bobbie. We had been friends since meeting in an improv class the year prior, were on a team together at the time and we always had a great rapport.

Plus, we had smooched a couple times, so even that sexual tension thing had largely been broken down. On top of those interpersonal positives, Bobbie was also an active guide with another expedition company in town, so getting up early and getting out of the city was nothing out of the ordinary for her.

I, on the other hand, really hated being awake so early and I was glad I had someone there with more energy than me.

Upon meeting up with our group, I quickly found that Bobbie wasn’t the only one with energy and the other participants helped me get excited for the day ahead. Leading the charge was BKO’s co-founder Stetson, who had set up the trip for me, and he was chock full of good spirits. There was a second official BKO guide and a girlfriend(?) of Stetson’s also along for the ride. Bobbie and I were picked up with another couple and a solo hiker in Manhattan before we drove into Williamsburg to make the second pick up.

We picked up a few more people in Brooklyn and made light chit-chat with everyone as we set out for “upstate” though I was sure people still needed some time to wake up.

There were three other couples with us in the 15 passenger van, and though they may not have exactly been on dates, I felt like this justified the idea that hiking could be a good time out for just about any couple. It was funny though, because I think Stetson (and ladyfriend?) were the only ones aware of the fact that Bobbie and I were on a first date. To everyone else, we must have looked like a couple that had been together for some time. Not only because of the atypical date choice but also, our level of comfort around each other.

One woman aboard the S.S. Outdoors Dating was particularly hilarious. Let’s call her Ginny. She seemed simultaneously excited for and scared of most things that lay ahead of us that day. It seemed as if this hiking trip was a big step outside the box for her, both in terms of physical activity and social interaction. Let me say first, good on her, really. Secondly, she was so odd.

We made a pit stop along the way, for coffee, snacks and a bathroom. It was a small little strip mall in some unremarkable little town and it was kind of perfect. All of us New Yorkers poured out of the van and into a little donut and coffee shop for recharging. It was great to get some coffee in my system as I had been addicted for nearly four years at that point.

The rest of the ride up was more social and lively and passed easily, as the entire journey was under two hours. People’s spirits were up by mid-morning and everyone was ready to rock as we cruised down 9W along the Hudson River and pulled over to the side of the road. By 10 a.m., we were ready to begin our hike.

We entered Harriman via a trail that wound up along with a mountain stream, which pooled right by the road, before crossing underneath and emptying into the Hudson. The initial ascent was a good jump start to an otherwise, up to that point, sedentary day.

A bit of the way in, we made our first steep climb and our friend Ginny was struggling. The second BKO guide, who was bringing up the rear, had the unfortunately task of waiting for her at each turn. By contrast, and I am not intending to brag, Bobbie and I were up at the front of the pack, following closely behind Stetson.

It took him a while, but eventually, Stetson asked me about the project and asked Bobbie and I how we knew each other, since this was a date. He was smart about asking, since I assume he waited until other hikers were out of ear shot, so as not to put Bobbie and I on the spot. It was nice talking to him about it and to have Bobbie involved in the discussion as well. We wrapped up that discussion by the time we made our first summit.

As we stood on top of what I think was Bald Mountain, we all took a collective deep breath. It was nice to take our packs off and shed our top layers as our bodies had heated up considerably on that first ascent. It was also roughly lunchtime, so we all broke into our stores of snacks and water. Bobbie supplied me with an apple from her bag and I offered anything of mine she might want.


One thing I loved about Bobbie, having known her for some time, was that she was deeply caring and prone to making everyone in a community feel welcome. Not only did that have a personal payoff for me, as she quickly shared her food with me, but she also readily struck up conversations with our fellow hikers. This made things both easier on me, a man who was actually somewhat shy at first in such scenarios, but also easier on the group as a whole.

After hearing that we did improv, one of the fellow hikers began talking to us about comedy and it turned out that he knew Arthur Meyer, a UCB all-star in both sketch and improv and then writer for Late Night with Jimmy Fallon, now a writer on The Tonight Show starring Jimmy Fallon. It was a really cool coincidence — not that I personally knew Meyer — but he was a virtual unknown in the non-comedy world, and I appreciated talking to someone who had seen him perform before and was familiar with his work. It was especially fun to meet said person on the top of a mountain.

He and I continued our chat as we set out on the next leg of our hike, descending down between Bald Mountain and West Mountain. We would be crossing from Bear Mountain State Park into Harriman State Park and though, looking around the forest, we saw little indication of the change, it was nice to be going downhill.

The group once again spaced out a bit and I found myself chatting with Bobbie more privately, as Stetson led the way along a trail which had recently been rerouted a bit.

There were certain topics I had never really discussed with Bobbie, such as her family, their hometown and their dog. She had one sister, who was married and lived in Illinois, and their family dog Sunny had died while Katie was in college. Upon hearing about these parts of her life, amongst others, it seemed to me that there were some glaring omissions in what I knew about Bobbie. Weren’t those things principal to most people’s world views and general lives? How had I made it that far into a friendship without knowing much of anything about her roots? I was glad to correct the problem to the extent that I could that day.

Though the downhill portion had been nice, we were soon climbing up our second summit of the day. When we reached the top, we had a bit more to look at and play with than at our previous location. There was a small, stone and wood lean-to, which looked like it had probably been built by trail authorities as a shelter for campers. We hung out in and around the lean-to for a while as everyone caught up and people gathered their energy. Stetson was an exception though — he kept his heart rate up with pushups. Oh, professionals.



One cool thing about bringing someone you hardly know to go hiking is that you can gauge how comfortable they are with peeing in the woods. Most men, I suppose, are fairly comfortable with the task of sneaking behind a tree or bush to take a leak, but it’s something I assume less women have done in their lifetime. They also typically require more cover, so the task is made more difficult. This was a non-issue for Bobbie and I, as we were both cool with relieving ourselves in nature. It merely occurs to me that it might be a funny litmus test for other, less-rugged people.

Speaking of which, I don’t think Ginny ever made it to the second peak. Somewhere between the first peak and the second, she had had too much of nature and the other BKO guide graciously escorted her back to the van to wait for us to return. It was too bad. She was entertaining.

The next leg of our hike put us temporarily on the Appalachian Trail, which Stetson pointed out by its trail markers. We dipped down to street level for a bit, encountering a dirt road on which we walked for a little while, but then it was back up to the ridge-line. We were avoiding a major parking lot and hiking entryway by climbing back up. Along the trail we continued, staying above most of the forest around us the entire time. From various vantages, we got to see Bear Mountain, so named because it looked like a giant bear sleeping on the ground. At the end of this ridge-line and trail was our third peak of the day.

Our last and final destination for the day was a descent into Doodletown, a ghost town buried in the middle of Bear Mountain State Park. It had been entirely vacant since the 1960’s, which really wasn’t that long ago, so it was really interesting passing through the town. None of the structures were still present, but foundations, stairs and some street signs were visible. Anything small and manmade had been grown over and it was fascinating to see nature reclaim the land.


We ran into other hikers in Doodletown, as it was a popular destination, and we caught our breath by the old town cemetery. Once refueled, we made the rest of the journey down old Doodletown roads, back to 9W and our van, which waited for us with Ginny inside.

Before hitting the road, we took one more chance to stretch our tired muscles and enjoy the last bits of the outdoors. Most of us hung around the small pool by the side of the road, snapping pictures and drinking water. It was a nice way to decompress after a long day of hiking.


Roughly 45 minutes after setting out from Bear Mountain State Park, our van pulled into a small parking lot behind an art gallery in Tarrytown, NY. This was BKO’s unofficial base of operations and, I believe, Stetson’s hometown. We were pausing to allow people a chance to treat themselves to a snack, coffee or, as we chose, ice cream. Also, I am sure some people took advantage of the opportunity to use a real bathroom.

Bobbie and I walked up and down Main Street and stopped into a couple different places, including Main Street Sweets, where we found fellow hikers getting ice cream. We joined in and enjoyed some of their homemade flavors for ourselves. We also stopped into a 7-Eleven, but for the life of me, I cannot remember why. It could not have been important.

Our stay is Tarrytown wasn’t long and soon enough, we were back in the van, heading towards New York City.

The sun was setting by this time and the van was quiet as fatigue overtook the group. I had been conscious of the dynamic between Bobbie and I all day. We had been flirty and kissy in the past, but by the time this date rolled around, I assumed I was 100% in the friend zone.

But when she pulled me closer to her and rested her head on my shoulder, so that she could sleep, I felt a closeness that had been absent the rest of the day, no matter how “comfortable” we had been with each other. There was something beyond improv-buddy friendship there, even if it was simply a deeper level of friendship, never mind romance. Seeing it, feeling it against my shoulder, put my mind at ease.

We arrived back in Manhattan just before 7 p.m. and we thanked our gracious guides. They had made the whole thing a real joy to partake in and I would absolutely recommend getting out of the city for a day and going for a hike. It was a blast.

Bobbie and I rode home together, as far as Queensboro Plaza, and then we split, going to our separate parts of Queens, but not before hugging and thanking each other.

Shortly thereafter, not even 8 p.m., Bobbie texted me.

Bobbie: Best shower ever. Thanks for a great day evan. …Is it too early to go to sleep? 🙂

Me: Haha. Maybe! Thank you though. You were the perfect date! 🙂

Bobbie: YOU were.

It was easy to go on 12 hour dates when you started at the crack of dawn!

For more information about amazing outdoor adventures like this one, check out Discover Outdoors.