Sophie Witter (left) and Sierra Bott plan peoples romantic outings for a living. Except, they dont know what theyll be doing until they arrive at their destination.
Sophie Witter (left) and Sierra Bott plan romantic outings for a living. Except, the participants don't know what they'll be doing until they arrive at their destination. Nathalie Graham

It's like solving an algebraic word problem and moonlighting for Cupid at the same time.

A form comes in. A couple wants to go on a date this Thursday. But, their budget is X, their dietary restrictions are Y, and they have to be home by 10 p.m. to relieve the babysitter. Oh, and it’s their wedding anniversary. Now it’s your job to design them an unforgettable night that they know nothing about until they arrive at their first stop.

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That, and more, is all in a day’s work for Sierra Bott and Sophie Witter, two of three operations specialists working at Mystery, a Seattle-based app that plans so-called mystery dates around the city.

Essentially, a user will select a date, a price point, and fill out their preferences. Then, they are whisked across the city in a Lyft ordered by Mystery, their destinations unfolding as they arrive. They're flying blind, while Bott and Whitter (and a good amount of handy-dandy software) are behind the scenes pulling the strings.

Mystery sent my boyfriend and I to a tea-making class followed by a speakeasy in Fremont last year. We did it again for his birthday (we went glassblowing), and then, weirdly, during Halloween (Zombie Can Can). Each time, we felt a mix of anxiety and anticipation, and a thrill in not having to worry about any of the logistics.

“And it’s not just that you don’t know what’s happening next,” said Bott, a former wedding planner and calendar planner at Seattle Events & Adventures, “but that whatever’s coming next is fabulous.”

After my dates, I desperately wanted to know how it worked and who was coming up with date ideas and how they were coming up with date ideas. Without ruining all of the fun—and the whole point and surprise of Mystery—I decided to find out. So I sat down with Witter and Bott in Mystery's Pioneer Square office.

Bott and Witter spend their days charting out experiences for couples, families, friends, coworkers, and whoever else. They told me about how they recently planned the first-ever Mystery proposal—“She said yes, for the record"—and how they sent a couple in their 70s on a date for their 40th wedding anniversary.

“They were so grateful afterward,” Witter said. “Which, like, phew. I was glad we pulled it off.”

They even scheduled a Mystery for a mother taking her daughter out for her 14th birthday. Witter said planning that required feeling 14 again. "But less angsty," she quipped.

The dates they plan are different. Witter describes herself as a wild card. “I like the quirky and eclectic aspects of Seattle, and try to use those in my dates.” Bott said that Witter is always good for a hole-in-the-wall bar suggestion or shows and performances.

Witter agreed, then added that Bott was “more cutesy and aesthetically pleasing—that kind of vibe.”

“I want to send people to these beautiful two-dollar-sign restaurants that, when you’re there, you feel three-dollar-sign ambiance, so people can experience a little VIP action, ” Bott said. In her free time, she loves to explore new restaurants and bars.

They each bring their lives into Mystery. And they can’t shake the job no matter where they go.

“My friends are always like, ‘You should send someone here!’” Witter said. Then, dryly, “And I’m like ‘We’re not sending someone to a water park, but okay.’”

It also requires some late nights and weekend work. Especially on Fridays and Saturdays which, understandably, are when Mystery has its peak activity.

When a mystery date is underway, there’s always at least one human making sure nothing goes wrong and adapting whenever anything does. There have been times when people arrive at a destination and it will be closed for a private event or the recommended food truck will have packed up and left early. Those are stressful, but Witter and Bott have cards up their sleeves to adapt.

“Ugh, but the problem we’ve really been having,” Witter groaned, “is the new tunnel downtown.”

The operations specialists are having trouble with the Lyfts trying to get to the Pike Place area because of the new State Route 99 tunnel.

“The GPS is telling the drivers that their location is in the middle of the tunnel and they get in the tunnel and it spits them back out in, like, SoDo,” Witter explained, “and the people on the date tell Mystery, ‘Hey, we missed our location,’ and we’re like, ‘Yeah, you’re going to be half an hour late for dinner now.’”

I asked them how they work around that since the tunnel isn’t going anywhere any time soon.

“We make sure to tell people not to let their Lyft drivers get into the tunnel,” Witter laughed. It’s extra funny because at the point, when people are picked up by their Lyft, they still have no idea where their first location is.

As the company, which is barely a year old, grows and expands, so does Witter and Bott’s workload. There are only three full-time people planning dates (the third, Amber Barney-Nivón, is a visual artist), and people are signing up for Mysteries all the time. The team is anticipating Valentine's Day will be one of their busiest days yet. There are already 80 dates scheduled, which is the most dates they've had on one night, ever. But, there are still slots open. It will be an all-hands-on-deck day and night.

A standard Mystery’s base cost is anywhere from $50 to $100. That makes it more of a special occasion kind of thing or generally just prohibitive to people who don't have that kind of disposable income. Recently, Mystery introduced one-stop dates that are a minimum of $20.

“It was a request we got all the time,” Shane Kovalsky, one of the co-founders, told me. “‘Mystery is great, but I have a date night every Wednesday—could you make it just dinner or drinks or a one-stop activity?’”

So they started offering a Mystery experience whittled down to just one thing. You can pick between a meal that Mystery chooses for you and your date, or one activity. Kovalsky said he became obsessed with pottery after trying out a class for a Mystery.

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Regardless of the number of stops or price points, Bott and Witter will be doing all they can to make the evening feel magical.

"I just always feel emotionally invested in these people who I don't know having an amazing night," Bott said.

"We're like love doctors," Witter added.