Bringing in the New Year Urban Style: Samson in Santiago


Santiago, Chile.

NOTE: This is another one of my process-y and highly personal posts. Not a lot of bike riding or amazing scenic places. More about contrasts. Between wild nature and metropolitan density. Between solitude and intimacy. Between self-sufficiency and requiring help. It’s all very vulnerable for me to share, but honest expression is what this blog was always meant to be. It has become my gratuitous commitment to write about the full range of my experience, to avoid omissions due to possible overshares, shame or just being “too personal”. So if these things interest you, read on! If not, the biking/nature/exploration continues in the next post… 


I rolled into Santiago after a hellish day of sweltering heat and powerful headwinds, most of which were felt from the shoulder of the first 10 lane highway I’ve ridden in longer than I can remember. As cars, trucks and semis blasted past at overwhelming speeds, I reflected on how lucky I was to be in this place as rarely as I am. Those cyclists who opt for the paved routes perhaps find themselves here more, and quite honestly, I’d have quit my journey long ago if this were my primary experience. But there were no side roads, no dirt options to get through to Santiago from the North, so highway it was. Upon arriving into the busy downtown, the streets were full of people walking, driving, and even biking. I turned one corner and was amazed to see the first urban bike-share station in all my Latin American travels. I’m sure there are other cities that have them, but I tend to avoid cities… 

I headed straight to Una Velocidad, the preferred bike shop of my one contact in the city, a Warm Showers host I’d met back in Northern Canada back in the Summer of 2014 by the name of Stephanie. She’d since moved to Santiago full-time and kindly offered me a place to crash for a few days. Luckily the mechanics at Una Velocidad were incredibly welcoming and let me leave my bike there so I could wander around town until Stephanie was off work. They also kindly agreed to have my replacement Rohloff hub sent to their shop from the USA so I could continue heading South. The trouble is that postage to Chile could take anywhere from a few days to a few weeks! Accepting that I might have to keep myself busy in Santiago a while, I wandered to the nearest internet cafe to make some calls, research the area, and do some other internetting… which eventually always leads me to Tinder…

I’ve yet to write much about my experience with dating in South America, especially online dating. The reason is that I’ve truly not done a lot of it. I’m just not that great at schmoozing/pickups/introductions with women. It’s as if there’s some psychoemotional forcefield which separates the Scott which is totally comfortable meeting new friends from the one who wants to meet new romantic connections. I get awkward, quiet, tight, retracted, and it’s just really hard for me to break through all this to make a connection. My timidity has often then led to awkward situations which further reinforce my doubt. There was the fiasco with a woman back in Colombia in which I thought we were connecting one day, but then ended up having to listen to her having sex with some other guy in the very next room on the very next day due to my own misunderstanding of the situation. Not a confidence enhancer to say the least. Many other solo travelers I’ve met seem to use Tinder to help make connections. When I was told about it the online dating platform it was supposedly designed to be a hook-up site. Given that the only information you can put on your profile is a few photos and words, it seemed perfectly oriented to that purpose. Since then Tinder has evolved into a place to meet anyone from activity partner to a life-long relationship, but for me it has mostly led to dead ends and annoyance. Given that both people have to “swipe” one another in order to make contact, I rarely matched with any women I swiped and when I did they rarely accepted my invitations to meet in person. It seemed most people just liked swiping through the images, another platform for wasting time online. Can you tell I’m bitter?!?

I was however in a big city for once and given the high likelihood of many Tinderers I decided to give it one more shot. To my surprise I matched with a few women right away, and one of them caught my attention far and away. As I said, you don’t get much to go on with Tinder about the person. Many don’t even write any words about themselves, just posting photos. That said, Dalila was gorgeous. So beautiful that I couldn’t quite believe we matched. I wrote her immediately and found her messages to be witty, smart, and warm. Likely that would be the extend of that however, given my track record. So when our conversation fluidly transitioned into making plans to meet up… that very day… in a couple of hours… I was dumfounded. I was exhausted from the day’s long ride, and honestly would have rather met another day, but she had plans the next night and was heading out of town soon thereafter.

Be here. Now.

I coached myself a bit to step forward in that moment, off the cliff toward unknown possibility. 


(NOTE: All the following information and images are being shared with Dalila’s expressed knowledge and consent.) 

And so went the evening: Met up with my kind host Stephanie, two years and 25,000 miles later, for a quick burger followed by a 2 minute shower. Dressed in my “fancy clothes” (my one pair of pants and long underwear shirt, with an alpaca scarf for flare… and my cleated bike shoes…), and found myself getting on a subway for the first time in 4 years for my first date in many months. Running purely on adrenaline, I got off the subway at the nightclub hub of Santiago. The streets were flooded with people. Music was blaring out of every doorway. Lights sparkled from every street corner. I wandered into our arranged meet up, a jazz club inside a courtyard, and our eyes met. I was so nervous. My need to just be my honest (albeit insecure) true self and my desire to make a good impression collided within my chest, rattling against my ribs like WWF wrestlers. But her warmth and easy going demeanor quickly calmed my internal clamor. We shared a couple of drinks for social lubrication, listened to the mediocre music, but mostly talked. For about 4 hours straight. It was lovely. So easy and natural. By the time we realized it was after 1am it was time for her head home to check in with her daughters, so she invited me to join her. 

But what does that mean? I’d be entering her home, meeting her children, as some guy she just met. Definitely pushing my “avoid being a sleazy asshole” button. But then we talked about it. I shared my trepidation and she shared that she’s never brought someone back to her apartment on a first date. But somehow it felt okay. Everything was feeling so good, I decided to just go with it. 

We arrived to her place and two of her daughters were still awake watching TV. While feeling warmly welcomed, I felt awkward. After a while the girls went to sleep. It had been so long since I’d felt any sensual touch, every point of contact sent surges of electricity through my body, two feet touching, palms and fingers intertwining. It was so intense I really hoped she didn’t want to rush into things. And she didn’t. We simply cuddled for a while, and fell asleep. It was exactly what I wanted.

 I awoke on Dalila’s couch a few short hours later with minimal rest to meet her 3rd daughter awake and excited to start a new day. We a slightly awkward breakfast and headed back to Stephanie’s place to regroup, making plans to see Dalila in a couple of days. Stephanie and her boyfriend had invited me to a New Year’s party at some famous astronomer’s house up in the hills above Santiago and we’d be leaving in a few hours to ride up there. No rest for the weary! Still relying on minimal adrenal levels to overcome maximal exhaustion and sleep deprivation, I followed my new friends out by twilight toward the party, our group size growing as we rode to a band of 7 bikers equipped with booze and snacks. While the party was a lovely bunch of folks at a gorgeous house with a pool and view, my energy levels got the best of me. I passed out on a hammock slightly after midnight as the party roared on around me. I was pretty embarrassed to have made such a poor showing but luckily Stephanie and her boyfriend graciously understood. 


 Over the following 10 days I got to dive into connecting with Dalila. Her daughters had already left to spend the holidays with their Father in Southern Chile, leaving us alone for a few days before her own flight South to visit old friends. It had been so long since I had open, relaxed time to feel romance, intimacy, fun and joy with someone. We laid around parks, attempted to go see good live music (usually failing in some peculiar way), even took a trip out to Valparaiso for a beach day. 


 Yes, mate was a regular part of every day. Curiously the tradition of sharing mate is much more Argentinian than Chilean. Since Dalila has one parent from each country she blends them fluidly.

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 We spent an afternoon in her local park watching the vendors roll by, climbers scaling the old factory silos above. 

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 One night we did make it out see some live music with Stephanie and her boyfriend Olaf. It began with a woman screaming into the opening of a snare drum as the microphone fed back cacophonous clamor. It progressed to all sorts of odd performances including this tuba/vocal duet. Very weird, but I loved it. 

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We definitely embraced the urban opportunities. First movie theatre in over a year. So of course we went to see some crazy action movie in “4D”. I’d never heard of such a thing before and wished I’d never learned… Each group of 4 seats moved separately from the others, rocking an jostling in time with things flying and smashing on screen. When an arrow shot out of the 3D screen a small air jet embedded in the seat behind our heads puffed air by our ears to convey it had just missed us. By and large, it was extremely overstimulating and distracting, but that seemed to be the theme of our odd nightly entertainment explorations and being together made it all just fun. 


 I spent part of my time with Dalila distracted, dealing with repairs. Some of my bike bags’ zippers were destroyed or in need of repairs, and I was nervously calling the bike shop every day to see if my replacement hub had yet arrived from the USA. First stop: Choike Bike Bags. Yes, there are 2-3 bikepacking bag companies based in Santiago, but these guys seem to have the best designs. They kindly took on repairing my bags while I watched and learned about their small production company. Such great guys! They even invited me in for lunch with their family. 



I loved watching the process of how they studied the stitching of my bags, and collaborated to come up with a durable solution to my broken zippers and damaged closures. A few hours later I left with good as new bags and two new friends. If you’re ever in need of fantastic bikepacking bags and/or repairs in Santiago, look them up! Choike Bike Bags!

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 Next errand: replace my old trusty wool long-sleeve shirt that accompanied me over 3 years of adventures. Luckily (kind of) Santiago has tons of enormous malls. I can’t remember when I’ve last been in one, and I can clearly say I’d rather avoid returning. Endless reminders of all the stuff being made and how much we all need to have it. Found a deal on a shirt and got the hell out.

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At long last. 10 days later, my replacement Rohloff hub arrived. This was the 3rd time I’ve actually been inside the mysterious innards of this clock-like neural network of gears and bearings. Luckily the dealer had opted to just replace the whole internal mechanism rather than have me attempt to fix it, so I just had to pull one one and throw the other in. Easy peasy.

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I have to give one more shout out here, to the kind, warm and hilarious bunch of mechanics at Una Velocidad. They were so amazing to let me use a bike stand and take up space in their shop for a number of hours while I performed the operation and a number of other maintenance jobs that were long overdue. I did my best to repay the favor with beer and empanadas, but their kindness was impossible to match. 

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 As Dalila’s planned flight South approached, so too did an overwhelming fear in my stomach. What was this thing we were doing? Where was it going, if anywhere? I was loving our time together, but noticed I was holding back on some levels, protecting myself from getting too attached to a situation that seemed to have no future. After all, I’m a poor dirtbag bike addict in the middle of a journey. She’s a mother of 4, 3 of which would be under her care for years to come, living in a dense urban environment. We were in such different places in life, and I just couldn’t resolve it in my head. 

But Dalila took a different slant. She decided to open her heart to the flow of this moment, here and now. She knew all the same facts that were shutting me down and chose to focus on her feelings — of connection, of love. It was beautiful, inspiring, and extremely nerve-racking to behold, because I couldn’t fully do the same. On the morning of her flight South, she changed her mind. She cancelled her flight and entire trip South, just to have a few more days with me. It felt so incongruous that I, the one with no responsibilities, was more afraid of the future than she, who had so many more reasons to be detained by reality. She always wanted things to just flow, but I couldn’t reconcile how to do that given our constraints.

For the most part, we justavoided the topic. Our budding connection seemed to have no clear pathway forward, but these moments together were beautiful and I didn’t want to let go. While my feelings for Dalila had been growing, so too did my anxiety about having no personal goal/intention that would support a choice to stay here in Santiago. I truly detested the feeling of city life, so I was deeply torn between my connection with her and a draw back toward nature, quiet, and wandering. Really I just wanted her to want to, and be free to, come with me.

The hardest part is she actually wanted just that. 

Having spent most of her adult life in Coyhaique, a small mountain town in Southern Chile where she’d raised her children with their Father until they separated a few years ago, she’d only recently chosen to try on city life. But she’d been feeling a desire to travel, then return to small-town Patagonia living somewhere. Her children, while totally happy living with her, were considering going to live with their Father for a while. But this transition, while possible, wasn’t going to happen any time soon. I simply couldn’t imagine living in the urban density of Santiago, waiting for some other life that might materialize “some day”.  What was I to do? Drop this beautiful and simple life on a bike to get a random job in Santiago, all in hopes that someday things might be different? 

We shared nearly 2 powerful and profound weeks together before my Southbound itch overcame a seemingly impossible future together. With bike finally fixed and fully functional, I was free to choose between motion and stillness, and as has been the pattern of late, motion prevailed. Certainly not without deep torment. Parting was painful, powerful, and painful yet again. It took me and additional 2 days to actually commit to leaving, which only happened once we formed a loose plan to meet up a few weeks later down South. So with widely mixed emotions I got back on my trusty steed, Dalila’s necklace mounted to the handlebars, and rolled away. 

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