Pinstripes: A Bold Type of Entertainment Hub

Nov. 22, 2019 update: Pinstripes will now open officially to the public on Dec. 3, 2019 after their community opener Dec. 2, 2019. Original Post:

As the surge continues with millennials making plans online to offline, moving from screens to scenes, the Bay area welcomes Pinstripes! Granted, if Pinstripes were part of a word association game, I’d get the buzzer, because when I think of “Pinstripes” my thoughts go to media and the hit TV show The Bold Type, all about a twenty-something fast-tracking trio of sophisticated media maven millennials in Manhattan, one with a love interest nicknamed…Pinstripe.

Apt as it may be, evidently my west coast lens is showing through, as THIS Pinstripes hosts an entirely different trio … bistro, bowling, and bocce ball, acclaimed throughout the heartland as an upscale entertainment and fine dining venue attracting millennials and more for multigenerational fun.

Pinstripes whimsical trifecta offers an Italian flair to kick date night up a notch, in a chandelier clad culinary bistro that serves as both fun fest and destination hub for casual elegance and a leisurely night of “adulting.”

It doesn’t fit the Hollywood portrayals of matching league shirts with embroidered names or gum-snapping bowling regulars named Madge (though I could envision a hipster retro Mad Men type of theme night to host an event like that) it’s a highly anticipated fine dining and event space opening here in San Mateo, CA with dual leveled grandeur that brings a whole new meaning to gaming, given the whisper quiet technology and private breakout rooms…so fercripesakes don’t call it a bowling alley.

For a Silicon Valley corridor brimming with young techies and iconic corporations like Sony Playstation, Survey Monkey, and the newest Facebook Oculus VR campus, there’s a dearth of local gathering places beyond the usual fire pit and heater lamp spots like Fieldworks and St. James Gate, and VERY little food selection that’s freshly crafted on site, so the new Pinstripes bistro with locally sourced fare will cater (literally) to all types of clientele with a pin drop target on millennials offering a welcome antidote to isolation, over work and startup burnout.

As one who tracks trends of how media and technology impacts youth culture, it seems like the “evolve or die” business mantra for large spaces like malls is seeping into social norm shifting as well.

As much as e-sports, virtual worlds and augmented reality dominate the gaming biz buzz, we’re starting to see a counter-balance of active vs passive gaming fun…with youth turning to hands-on activities like co-ed softball leagues, escape rooms, and outdoor adventures, Pinstripes is set up for a strike to leverage face time OFFline.

There are even social startups like the nascent Social Haus ramping up dialogue to reteach the art of conversation face to face…using a subscription “meetup” model to get humans reconnected and TALKING again.

The Social Haus theme swirls around the notion that you enter as strangers and leave as friends, whether it’s showing up for a retro ‘board game night’ or a sort of ‘speed dating with dialogue’ using table switching gamification of hands-on questions to open hearts and minds to sharing fun stories or new friend groups…And if “three makes a trend” look no further than the adaptive repurposing and redevelopment of museums for midweek mixers, from modern art to natural history.

Anyone who’s queued up for the long lines at the successful Cal Academy Night Life or Thursday evenings at the Exploratorium knows that they’ve successfully turned a ‘night at the museum’ into a themed adult event fest, complete with pop-up bars, yoga in aquariums, comedy amidst the critters, you name it. Repurpose, renew, relaunch, reconnect.

Truth is, the more screen culture takes hold, the more the need for offline connectivity becomes readily apparent…

…“Netflix and chill” only goes so far, gym time gets old and house parties only happen with an invite.

Even the 20-somethings in my own sphere have said, “where do you even GO to hang out and meet people once you’re out of college…everyone’s already found their friends!”

And it’s not just millennials, it’s families, kids and couples all feeling the need to “meet up,” share conversations, and connect offline…it’s a trend that is surging.

Pinstripes and its surrounding garden-like environs of fountains and chat nooks seem to fill that void as a sort of gathering spot to connect, expand friend groups and mix it up offline creating a sense of community beyond just the downtown city center.

The central peninsula location is sure to have universal appeal as well, particularly when it’s one of those ‘don’t feel like jockeying the SF parking or Palo Alto or Burlingame neighborhoods’ kind of days.

From cozy library style sitting areas to casual terraces and outdoor café tables, the flow enables people to find their own niche area to hangout, so it’s ripe for being an after work meeting spot as well as a corporate party or luncheon possibility.

Pinstripes has the potential to feel more like a ‘happening’ than a venue given their two-levels spanning 33,000 square feet of event space and private rooms nestled into nooks and crannies that make it feel like multiple places, not just one customizable venue. With made from scratch menus and seasonal fare as a focal point, along with craft beers and cocktails, an extensive wine list (and ideally plenty of community cross-pollination)…it could be a face to face enclave that’s much needed here on the peninsula.

Though the dozen bowling lanes and four bocce ball courts are a ‘team building’ natural, they’re also icebreakers to blend all ages together and turnkey entertainment for family fun, from private parties to large celebrations and full catering fetes with an Italian flair, handmade pastas, risottos, bruschetta, calamari, plank grilled filets, prosciutto and antipasto.

With the need to find popular enticements to repurpose malls with an influx of tony restaurants and social spots weaved into what was once ‘retail space,’ Pinstripes falls into the ‘something for everyone’ sphere…even kids’ birthdays.

When I first went to dinner at Paul Martin’s American Grill for example, I was incredulous that they’d placed an upscale ambience smack dab in a mall location, but now looking at the ‘master plan’ of redevelopment it’s clear Hillsdale had a larger lens to bring together work and play in its many iterations from the Palette Tea House to the luxury Cinépolis theaters.

Pinstripes is already doing a booming business in ten locations across the nation, from its origins in Chicago and the Midwest, to expansions on both coasts with San Mateo being the first California hub.

Slated to open December 3 in time for the holiday hoopla here on the peninsula, Pinstripes will soon emerge as an oasis for anyone looking to get off their screens, get out of the house and share some time together… I’m game.

Visual Credits: Pinstripes promotional materials (via hard hat tour) and online site. Fair use photography of smartphone by Daria Shevtsova via Pexel. 


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