It was the spring of 1999 at Slam City Jam, Vancouver, B.C., when I first saw her. She was busting super-clean nollie tailslides. She was super short, no more than 5’2” or 5’3”- but in her run, she flowed around the course like a seasoned vet. She had skinny arms and a brunette ponytail, with a black shirt and a pair of khakis. She had a clean kick flip as well.  She was not like the hesh-mesh females I knew from Burnside, nor was she like the padded up transition queens of the 1980’s. The pro female skaters at the time were 90 percent antisocial and mean-spirited, so I stayed away. She seemed different, and by that I mean happy-looking. That skater was none other than Jessie Van Roechoudt.

I was seeing someone back then, and didn’t even bother to say hi. I was intrigued by her, though. Shortly after this moment in time, an article on her in Slap magazine came out. She was attending San Francisco State and studying Anthropology. She was into bebop jazz,  liked coffee, and was well-read and brilliant. Her roots were from Kelowna, B.C.. Her mom was a flight attendant and she was well-traveled. She also seemed to have a very comedic way of stating things in the article. My crush- or you could say, “obsession”- grew. “Wow,” I thought, “she is good-looking, well-read, and educated, not to mention she shreds on a skateboard. I need to talk to her, some how, some way.”


Nate Sherwood, our esteemed storyteller of the month, with a backside nose blunt (left), and an ollie outside Eduskate, his skate shop in Cedar Rapids, Iowa (right).


A couple of years later, I was in the Birdhouse tour van on a road trip from San Diego to Lockwood in LA, paging through a Thrasher in my seat as we fought northbound Five interstate traffic. An ad with Jessie was in there for Genetic Shoes. I gasped and went, “aww”, and Willy Santos, as well as Jeremy Klein, were like, “what the fuck did Nate just see?” as they jumped over my shoulders and tried to get a view of what I was looking at. I explained it was an ad of this female I had a bad crush on. Brian Sumner, riding shotgun, cracked up super-hard and then turned and looked at me. He started to tell me a story how he had “relations” with her at  Steve Rodriguez’s place. All the guys in the van were high-fiving, Brian was cracking up, and I felt kind of bummed…. ‘cause you never want to think of your crush having “relations” with some dude you know. But yet, I was kind of happy and relieved. At least I now knew she was straight and liked men rather than women, which at the time was rare in female skaters. So I went from a shocked frown to a smile.

Fast forward another few months. I heard through the grapevine at Billabong, on a trip to their warehouse with Willy Santos to pick up some gear, that her birthday was in late-April or early-May, and that I should surprise her with a gift if I wanted to break the ice, even if it was just to talk to her.

I planned out my next Slam City Jam in Vancouver, which was in May of that year. I bought a book on Charles Mingus (the upright bassist), and another book on Margaret Mead (the anthropologist), and wrapped them up as well as I could. I spent hours drawing funky little skateboards on the wrappers, and skyscrapers. EMB and Hubba Hideout were on there, as well as the P.N.E. rail in Vancouver B.C.. I used skate stickers rather than tape to tie it all together, and my bow was a string of bearings wrapped in dental floss. I liked the mint smell it gave off. I was freaked of flying at this point in life (that is another story), so I drove from San Diego to Vancouver BC with the gift buckled in my shotgun seat.

I stopped in SF to see the owner of Elevate Trucks, Matt Cole. I needed some last minute goods to toss out at the comp. I also hoped I might run into her at any of the street spots I was to go skate that day and night. I then set sail to my motherland of Portland to pick up fellow Capital teammate Rodd Marks. I picked him up, and then drove to Seattle to my good friend Brandon Egggleston’s place to pick him up to hang and film, etc. Yep, before he was the guy behind the soundboard for such bands as the Mountain Goats and Modest Mouse, Brandon was my filmbot and childhood friend. Anyway, I had my posse of bros with me, and I briefed them on why I had this gift in the car strapped down like it was the Lost Ark and why I was going all-in on this caper and that whatever happened, I would deal with it.

Brandon was giving me a pep talk, helping me out. Brandon, although he would not admit it now that he’s married, was a grade-A lady killer. This fucker could get you free food, free drinks, free anything other than a car or house because he was a hunk. Women loved this fuck. To this day, if I go home to Portland women will walk up to me and say, “ I went to high school with you; you were that friend of Brandon’s, right?” Like they have no idea who I am at all, but they all knew him. Anyway, I was trying to study his TEO as if it was doctrine so that maybe I’d have a chance to break the ice with Jess and not look like the insecure fuck that I am. Rodd Marks had a whole different art of war. He was saying I just need to be “drunk before I go talk to her.” It was a great five-hour talk though traffic and apple orchards. My confidence was building.

We got to the border, and the Canadian border dudes searched the car because we all looked nuts as fuck. Brandon is a modern indie rocker: clean-shaven, smells good, and he had clothing on that looked newer than 30 years old. Rodd looks like he walked out of a biker bar and belongs to the Gypsy Jokers with a tat on his neck of a fucking six-shooter that read ‘Desperado’ on it. Then there was me: a nerdy-looking fuck with a button-up shirt and a bowl cut. They must have thought we were some crazy crime family smuggling guns and ammo into the Great North. They made us go to the inspection area; they kept asking us, “do you have any firearms?” We said “no, we are hippies.” See, Canada does not give a fuck if you have a key of coke or a bindle of H or a dead hooker in your trunk. But if you have a gun, you are fucked. That was all they wanted from us. A nice gun or four.

Anyway, when they got to my gift for Jessie they asked what was this box and who is Jessie. I told them it was a gift: two books for the crush of my life. The dickhead looked at me with the face that can only be described as ‘this guy is a pussy,’ but whatever. He held the box, then put it on top of the car. He was not stoked on us. They searched my car for half an hour; under it, on top of it, in it. They found nothing, of course. Anyway, they shook my gift for Jess and then they placed it in the back seat. As soon as they let me, I strapped it back in. We put all our shit back together, then we hit the road. Into Vancouver we went, happy as can be.


The object of Nate’s affections. Well, five years of them anyway…


Fast forward to three days later, the female portion of the contest was on. Some dude was interviewing Jessie, and some of her fans were asking for her to ink some shirts and whatnot. I grabbed her birthday gift from my backpack and skated up to her. I said, “Hi, Jessie, happy late or early birthday!” I smiled. See, I had no internet, so no Google for me. So I had no idea if I was late or early, but I knew I had to be close.

When I gave her the gifts, I froze up like deer in headlights. She responded, with a odd look on her face, “thanks for the gift.” Then I said, “your runs were epic.” She replied, “they were mediocre at best, but thank you.” She used big words like ‘mediocre.’ I was falling deeper into my crush from hell, but her crew came up and whisked her off and the camera man followed. Before I could get any more words in, she waved at me and I waved back. I must have looked like a dumbass, because right then Jamie Rayes skated up and said “are you high? Get off the course you fuck, it’s female day out here fool.” I skated away in shock, so happy that I got to speak with Jessie, and even more stoked that Jamie did not shank me.

A few months later, I got my internet and received this mass email from Bryce Knights about saving the Berkeley skate park from some toxic waste that was leaking into the bowls and shit from beneath the park. This was before blind carbon copy was widely used, and I decided to see who else got this same email. Every heavy hitter at the time was cc’d on this email: Danny Way, T-Hawk, even Koston. However, I was more stoked that Jessie’s email address was in there. So I emailed her, asking if she liked her gifts. I said I had received her email address from Bryce (not fully a lie, right?) so I wouldn’t appear too shady. She replied back, but it was very blunt and professional. After a few emails back and forth, I got a super optimistic idea that I might have a chance to just go skate with her or hang out, get to know her, etc.

My friend Stephanie Limb, mostly known for playing Peggy Oko in the film Lords of Dogtown, and I were skating one day at the sand gaps in Santa Monica. At some point Steph exclaimed, “do you still have a crush on Jessie?” I replied, “of course, I have for some time now. Why do you ask?” Stephanie went on to tell me that she was at an audition for a Hewlett Packard commercial, and that Jessie was in the office in the call backs as well. Stephanie said, “I told her I was friends with you, and she said ‘that guy is creeps me out, I heard he did porn.’” Steph went on to ask me if I did porn. I felt like my world was over. My innocent crush was crushed. Steph went on to say, “you might want to stop the emails and try to talk to her in real life to straighten it out.” I agreed, and then again denied all accusations of me doing porn. I had no idea who was life-blocking me, but I was out for blood. Some asshole planted a seed in her mind that I was a fucking player or some shit, and I needed to get to the root and stop this shit.

How was I supposed to bring that up in an email, anyway? Like, “Hey, I heard you heard a rumor and think I am a creep. Well, I’m not.” Blah blah blah, etc. Who the fuck brings that up in a email? And how crazy would I look saying that anyhow? That would only make me look even more guilty.

Two years go by, many relationships fail, one with this chick Megan who looked like Jessie. No joke, I dated her just because she looked like my crush, but she didn’t have the personality or the book smarts that I was drawn to so badly. And I was still in crush mode with Jessie. I will save that one for the shrink.

At this time, my friend Adam Sullivan was working at the Skateboard Trade News mag, and he had hired Jessie to be a contributing writer. Knowing my crush on her, he sets up a session for us to skate some red curbs and go get dinner and drinks with his wife Ann, and Jessie. Two days before she flies into San Diego, I get sick with the worst ear and sinus infection I’d had in years, but I knew I had to set the record straight. I knew I had to prove I was not a porn star, or some misogynist or sexist fuck, or at least get coffee with her and talk it out. Plus, I wanted to know what enemy of mine was trying to poison the well by making up this porn rumor.

The phone rang. It was Adam: “Yo, Nate, red curbs tonight at 5 pm?” I was like, “hell yes.” I ate four Sudafed and puffed my Afrin and Flonase. I was trying not to look completely dead, but I was someplace between the pale of Darby Crash and the white of a Motel 6 wall. I got my ears to pop, I showered, made myself not smell bad, got rid of my Nyquil breath, and I grabbed my board and headed out to shred with Adam, Ann, and Jessie.

When I got to the spot, it was packed. Cullen Poythress was there with a launch ramp he brought from home; the late Eric Striker (rest in peace) was there, and of course Adam and Ann, plus the person I wanted to hang with more than a Catholic wants see the Pope: the one and only Jessie, as if a beam of light was surrounding her. I was shaking, so nervous. The gold standard of women was right there in front of me. “Not the time or place to bring up your bad rep”, I told myself in a repeating mantra manner, “just be cool, be chill, skate it up”.

Eric Striker, that fuck, says to me, “Nate, do a nollie flip!” I am as high as a gas huffer on the international space station, fidgety as hell! So I bail a nollie flip, and land primo. Jessie saw it, and that made me feel more insecure. I went about doing my normal pressure flip overdose of shit and we all had a fun session. Jessie even clapped for me when I busted an ollie up this launch ramp the hard way. My confidence was up enough to talk to her. I clapped for her when she did a bolts-perfect Nollie 50-50, and she seemed in good spirits and was nice to me. We chit-chatted about normal shit: the weather, the flight down, writing, Buddha, and how karma worked in the world. Nothing too heavy yet. We just skated; I didn’t want to piss her off or piss myself just yet. I was on a lot of drugs, and pissing in my pants seemed like a good idea. Hell, I was dizzy as Gillespie and higher than a hippy in a tree fort. After it got dark, the Transworld gang left, and Adam suggested we go get dinner and a beer.

We were off to Islands Burgers on Airport Road in Carlsbad. Adam, his wife and Ann, and Jess were in his Honda; I drove separate. I was in my beat up Volvo wagon rolling solo like a stalker should behind them in traffic, using snot rags to keep my nose from looking wet like a damn canine, and doing my best to try to play it off like I was healthy, leaning forward over the wheel like the guy in the film Repo Man who had the nuke in his trunk. I feared getting anyone sick, but at this point I had waited five years to sit down with her and have a beer, and I was not going to let a cold fuck that up.

At Islands we got ourselves seated, and I had this gut feeling that Jessie was a vegetarian. For some reason, I think every person in SF is. I know that is a stereotype, but I was high as fuck on antihistamines. I was seeing visions of God at this point, let alone trying keeping my game sharp.

I was the first to order. Adam put me on the spot, like, “order first, Nate!” I said, “I will have a Boca Burger please, with guac and a house salad.” I did not want to look like a pig in front of this goddess. My palms were sweaty like a heroin addict going through withdrawls. Then it was Jessie’s turn to order. I was dead wrong with my stereotype: Jessie ordered a damn beef-as-fuck burger, huge Megatron-size, and draft dark beer. I was scared now because I received that look from her, like, “this guy is a pussy, I love red meat,” so my self-esteem now was in the gutter once again. Out of respect I didn’t order meat, and here she was, eating a damn burger that looked like Fred Flintstone made it and a beer fit for a damn Viking queen. I drank my little crafty art-fuck beer and ate my Boca burger. I had to run the role I was playing now. There was no return after that fuck up. Adam looked at me, like, “damn, Nate is biffing his shit left and right.” Plus I was shaking like a damn squirrel due to the large amount of drugs in my system.

After dinner, Adam had the idea to show Jessie the Carlsbad High School gap. I tagged along like the love-sick puppy that I was. When we all got to the spot, I was higher than Keith Richards in ‘76 from all my nasal drugs, and this cold was kicking my ass. As we walked from the cars to the spot, Ann and Jessie made jokes and I talked to Adam, and as we walked across the football field to the side where the gap was hidden, we all started to geek out on all the tricks that had been done. Ann outright says Kris Markovitch kickflipped it. I went on saying Jeremy Wray frontside 360 ollied it. Jessie just looked at it, and had that look off an artist who was viewing a blank canvas. Then I said, “P-Rod almost fake tre flipped it. I heard that was a rumor, at least at the time. I caught from the Syndrome dudes that he was attempting to fakie tre flip the fucking C Bad gap.” Jessie went off; she was not a fan of P-Rod. I will not gossip here, but I think P-Rod rocks. She clearly did not, and we both decided to humbly disagree. To this day I have no idea why, but she gave me a strange half-mouth grin and said, “I don’t like his style.”

That made me lose some respect for her. My crush was not as strong after that. I found something that made me not like her. I could live with a small thing like that. Who is that shallow, right? Not like a thing like that could change an outlook on a crush that was five years deep at this point.

Then somehow the conversation got changed to how automatic garage doors are for the suburbs, and people in the city have a garage door that has to be opened by hand or no garage at all. Adam and Jessie argued this in an intellectual manner, and I went from stating it to just listening to how they rambled, happy that the heat was off me. I think P-Rod is great, but I also dug her defiant ways against the norm and I was still crushing hard.

We then went to the Von’s grocery store down the street to skate and look at this loading dock ledge spot that Patrick John Ladd, better known to anybody reading this as PJ Ladd, had some clips on. We all sat on the ledge after skating for a few minutes because it was too dark to sesh. We talked about skating some more, and then Ann yanked out a yawn and Adam followed suit, and I did the same. Jessie had the look of ‘I am beat.’ Now was my time, my shining moment, to try and get her number before they all said their goodbyes and good, nights and made their way home to Adam’s house to crash out. I needed a window to get her number. ‘We could get coffee,’ I thought. ‘Yeah, that sounds good.’ Then maybe I could change her mind about me.

Adam and Ann walked to their car and Jessie was following. I sprung up from the ledge with my Nokia silver candy bar in hand and said, “Hey, Jessie, I’m not sure if you are free tomorrow, but I would love to go get coffee with you in the morning.” She looked at me like I was a moron and she saw my phone in hand, queued up to program her number in. That might have freaked her out even more. I then said, “Can I get your number so I can phone you before I pick you up?” She still looked at me funny. I repeated myself, thinking maybe she had not heard me. ‘A lot of people never hear me when I talk to them,’ I thought. She then said the sharpest words I ever heard in my life to this day:

“I check my email daily.”

I asked one last time, but she replied again with, “No, I check my email daily.” I was about to tear up. I said, “Ok, well, I will just email you then.” She gave me the look of, ‘I am shooting you down you idiot, get it through your fucking head, you are not my type, fuck off, and I don’t feel safe giving you my number you are insane, leave me alone.’ I could read that from her Canadian death stare, the same look Bobby Ore gave Detroit in the Stanley Cup finals. “Sounds good”, I said in my best chipper mode voice. Thank god I was high as fuck on meds, or I might have died right there on the spot of a broken heart. I think everything felt like a dream sequence, and not real. Adam gave me a look of, “Oh, damn! Poor Nate, that had to hurt!”, and even Ann had a look of pity for me. I said goodnight to them all, and waved goodbye as I skated away to my car.

I knew she was not that eccentric. I knew that email was not her choice of communication, and it hit me hard that this was a shoot-down. It was a brutal one, to say the least. She did not trust me with her number. I had Chad Muska’s and Jamie Thomas’ and Daewon Song’s number in that phone, but yet hers was more guarded than theirs. It was as if hers was sacred. “Who the fuck does she think she is?”, I thought for a second. Then I got in my car and waved goodbye to them as they drove out of the parking lot the exact opposite direction. I drove down Tamarack Street, headed back to P.C.H., to go northbound to Oceanside, and then it hit me in the face like a wet fish. “I worked on that crush for 5 years”, I said to myself, “what the fuck did I do wrong?”

I cried so hard. Like an infant. I cried so much I could not control my car, so I pulled over at Squid Joe’s. It was a dive bar at the time. I sat in my Volvo crying with tears all over my face, and I keeled over with snot coming out of my head like a fire hose on crack. The drugs did not help, but I was mental as fuck. I had used all my tissues in the glove box; thank god I had a case of new t-shirts that Mark Waters at Es Shoes had shipped to me. They became snot rags. My eyes were so glazed over from my tears I could not even see the AM/PM gas station sign across the street. I sat there for it seemed like an hour trying to get my nerves back in order so I could drive safely. Two Carlsbad police cars rolled up. They lit up their lights and came up to my window, asking me why I was loitering in the parking lot of this bar for so long. I am sure the bar keeper called them. They were out DUI hunting, and I knew I was in the clear. I had more Sudafed in me than a meth lab. That shit is legal for some reason, fuck if I know why. I then vented to the officer as I was crying: “I just got shot down by the women of my dreams officer, it was horrible. Five years I’ve been trying to just hang with her get to know her and she said to me and I quote ‘I check my email daily.’” The cop, trying not to laugh, said “Damn, that sounds like a shitty day! You just sit there as long as you need, son, and get home safe.” I said, “Thanks, dude”, and rolled up my window.

I sat for a bit to deal with the gravity of the situskation. I then noticed an old, beat up Vice Grip on my passenger side floor board. It was oxidized like it had been sun burnt. Then I put it all together. Life is a Vice Grip; every hour it gets a bit more tight, and if you can’t roll with it, you better jam it before it crushes you.

I got home hours later and I wrote Jessie an email, even though I knew there was no chance at all. She never returned fire. And that was how it all ended. I went on to live a normal life. If you invest five years of your life into anything, get a degree rather than basically stalking a woman. It is not worth it. Worst five years I ever wasted. The amount of hours I spent doing that could have gone into building a company, owning a shop, or getting a degree in something that made a buck.

I’ve had to deal with a lot of creepy people over the past six years. Owning a skate shop means dealing with a lot of insane people. I think it might be my karma paying me back for creeping her out.