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It’s happened a couple times now. I walk to my car from Zeitgeist Coffee or gaze up at the old brick at Occidental Park and think, “Why don’t I hang out in Pioneer Square more often?” Then I look around, realize I’m one of two or three stragglers out and about at 7:30 p.m., and remember.

Everybody went home — somewhere else.

With Zynga and now HTC joining companies like Isilon Systems, BlueNile, Yapta and Payscale there, Pioneer Square is proving it’s a place where geeks want to work. But until Seattle’s first neighborhood stays up past rush hour, it won’t rival Fremont, downtown and the booming South Lake Union as a place where geeks want to play.

Though it really, really should.

I mean, look at it. The benches. The cobblestones. The lampposts in fog. What better place to toast the future than on this rustic, uneven surface studded with relics of Seattle’s past and accidental tributes to its insecure present? When you get down to it, Pioneer Square is the most beautiful neighborhood in the city, precisely because it’s so mismatched. Homeless centers light neon signs. “Weirdo” murals work wonders. Even that hideous “sinking ship” parking garage has a certain charm.

Pioneer Square has the space. To have the vibe, it needs people, and not just 9 to 5. You could point to lots of reasons why they’re not turning out in droves, but since the legendary Elliott Bay Books made its headline-grabbing move to Capitol Hill last year, the area’s been drowning in feedback. The need for activity is a known issue neighborhood champions are working to fix, celebrating the area’s character, executing promising ideas and pointing out when they believe things are better than they seem.

Mónica Guzmán

One of the most vocal among them is resident Jen Kelly, who writes the New Pioneer Square blog (and is married to Banyan Branch Director of Operations and Finance Michael Kelly). The way she put it to me this week, whatever the diagnosis, the cure is a critical mass of people who get out into the neighborhood and feel like they have a stake in where it’s going.

The treatment is… tricky.

“Pioneer Square is every shade of gray you can imagine,” Kelly said. “You have to work within those shades of gray.”

Drawing new residents is key. Visitors don’t always see Pioneer Square as a place where people live, and current residents will tell you the rowdier ones act accordingly, especially after Seahawks games. (Sounders fans, I hear you’re better behaved).

Hope, for some, is coming in the form of 444 apartments going up on the north end of the CenturyLink stadium parking lot, a project that broke ground last week and is the first phase of a residence and office complex the county says is projected to generate $727 million in economic activity over the next decade. But that’s just a start.

Tech employees have a part, too, when they can play it. The neighborhood’s location, transit access, architecture and wealth of cheap lunch spots have served Pioneer Square workers well for years — during the workday (though higher parking rates hurt and faster Internet is promised). But as any networker will tell you, attachments form better at night. Not just with people, but places, too.

Thing is, whole swaths of the neighborhood shut down with the workday, leaving some great bars and restaurants off First Avenue (ever been to the Owl and Thistle?) as lit-up islands in the middle of lonely, sometimes spooky streets, or closing down an area altogether. After the popular (but WiFi dryCaffe Umbria closes at 6, there are few ways to take in the tucked-away romance of the plaza south of Occidental Park other than with a quick stroll. Unless, of course, it’s time for the once-a-month Art Walk, when the area truly comes alive.

As the neighborhood changes — if it changes — so will this dynamic. And on and on until, maybe, someday, Pioneer Square is as cool as it was meant to be.

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