Have Tinder, will hike Chilkoot Trail: Couple goes on epic 1st date

Tess Astley and Lory MacKenzie first met on Tinder and then only briefly in person before they headed out for a five-day hike of the Chilkoot Trail.

First date is a 5-day mountain hike for adventuresome duo through Alaskan and B.C. wilderness

Tess Astley suggested hiking the Chilkoot Trail as a first date to Lory MacKenzie, who agreed. (Tess Astley/Instagram)

For some, a first date can feel like it dragged on for days.

For Tess Astley and Lory MacKenzie, their first date actually took five days — they hiked the Chilkoot Trail together — just a day or so after meeting in person.

They have no regrets.

Call it a post-modern pairing only possible in the age of Tinder, the dating app millions of strangers use every day to become otherwise. Call it the longest first date in the world.

But don't call it a last date.

"We didn't really make any plans afterwards, but here we are talking pretty much every day," said MacKenzie. "I definitely think that there's going to be a second one."

Astley lives in Whitehorse — she's stationed there as a nurse — and MacKenzie lives in Edmonton.

He's kind of a handsome guy, so I wasn't disappointed.- Tess Astley

Astley had been looking for companions to hike the Chilkoot Trail, a mountain hike about 53 kilometres long from Alaska to B.C., but wasn't having any luck.

Meanwhile MacKenzie, who uses a version of the Tinder app that let's him scout for dates beyond Edmonton, was making plans of his own.

Surprised but excited

He tuned Tinder to the Whitehorse area, where he expected to travel. That's when he met Astley on the app. He wasn't necessarily looking to hike a multi-day trail as a first date, but Astley pitched the idea.

"Within an hour of us talking, she had brought up the Chilkoot," MacKenzie said. "I was really surprised that she was adventurous enough to have suggested the hike and I was really excited about the idea of it."

MacKenzie made the drive from Edmonton to Whitehorse in his Jeep, looking rugged with its doors removed, loaded with camping gear for two.

"He did come with a lot of supplies and he actually dropped off a backpack for me the night before the trip as well, so I could pack," Astley said. "But he looked very outdoorsy. And he's kind of a handsome guy, so I wasn't disappointed."

I was really surprised that she was adventurous enough to have suggested the hike.- Lory MacKenzie

Together they drove to Skagway, Alaska, to start the hike on the nearby trailhead. They were five days on the trail, lugging their gear over a mountain pass, and camping along the way.

"We were really lucky, we had great weather," Astley said. "I feel like it went pretty fast because it was our kind of first time [getting] acquainted, so we did have lots to talk about."

MacKenzie agreed, saying the conversation was "organic and natural." 

They were matched in other ways as well.

"We're both the same physical fitness level, so we weren't waiting for each other on the trail," he said.

This kind of extreme first date was outside the usual for either of them, but the stunning views and constant activity made for a natural way to get to know one another.

"The weirdest thing is just how much you talk for those five days," Astley said. "I feel like I knew Lory for months when really I had just met him. This was our first date."

One more weird thing.

"We're both from Edmonton," Astley said. "We actually live five minutes apart."

Written by Walter Strong, based on an interview by Dave White


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