When most folks in Silicon Valley think of going on a date, they immediately think of heading up to San Francisco. And it isn’t a bad idea. Between the great restaurants, exciting nightlife, and amazingly beautiful views, there’s a reason why everyone who lives and works in the valley prefers to play in the City.
Of course, Silicon Valley isn’t quite the suburban wasteland it’s often made out to be. Longtime residents usually have a reliable list of go-to date spots that have been around here for a while. Whether you live down in South Bay or even live in the City and want to mix it up with an excursion down the 280, here’s a list of some date spots in Silicon Valley, some places that served me well back when I was single. Whether you Tinder, Grindr, or Hinge (or Meet your Bagel), I hope you have as much fun taking dates to these places as I did.
The Classics
The Hedley Club
When I first moved to the Bay Area back in 2008, I had a slutty friend who took every single date to the Hedley Club. He described it as “classy, serves great drinks that are really strong, and just unique enough to not seem like any old date.” Before long, I started taking every one of my dates to this place. It’s an old school lounge in the DeAnza Hotel in Downtown San Jose, the place looks like it came right out of a Prohibition era gangster movie. The bartenders are all dressed really snazzy, and there’s live jazz every night. Since then, word seems to have gotten out about the DeAnza Hotel, and now it seems like there’s at least 3 people on first dates there on any given night. Which is not necessarily a bad thing — if you and your date run out of things to talk about, you can always have fun commentating on the awkward first dates going on around you.
Rooster T Feathers Comedy Club
For being a comedy club located in a strip mall in Silicon Valley (Sunnyvale to be exact), Rooster T Feathers manages to attract some big names. It seems like sooner or later, everyone who lives in Silicon Valley ends up here on a date night eventually. This place always has a small, intimate crowd, perfect for the comic on stage to have some funny interaction.
Golfland USA
A short drive down the street from Rooster T Feathers, there’s a mini-golf spot. It’s the perfect spot to re-live that one awkward date you had in middle school (if you were cool enough to date in middle school). If you go there on a Friday night, you can see lots of ACTUAL middle schoolers going on awkward dates here, which always somehow manages to be sweet, cringeworthy, and hilarious all at the same time. Extra points for having an arcade on-site, proving that the proprietors are well aware they’re operating in a region full of nerds. Given the self-aware cringiness involved, this spot is best left for a date with someone you’ve been seeing for a while.
Moving Meal on Castro Street
Among Googlers and start-up types, Castro Street in Mountain View is something of a default option for first dates. The appeal is understandable: a bunch of restaurants in close proximity, all with extensive cocktail menus, all serving food that manages to be both decently good and completely unoffensive. That being said, getting dinner at a single place on Castro Street often seems like the Ed Sheeran of first dates: dependably boring, checks off everything on the list, yet devoid of anything truly interesting. Given that every restaurant on Castro seems to have solid cocktails, great appetizers, and mediocre entrees, I recommend stepping things up a notch to a vaguely more interesting Sam Smith level by hopping different places for appetizers walking down Castro? A few of my personal favorites are izakaya at Bushido, followed by pizza at Doppio Zero, topped off with dessert from Alexander’s Patisserie.
Stanford Theater
Like the Hedley Club, the Stanford Theater has an old school classiness right down to the old movies that they show and the pipe organ that they use for music. On most nights, you can catch the adorable sight of Palo Alto senior citizens watching black and white movies with their significant others. Then you can reflect on how those same Palo Alto senior citizens bought their houses on the cheap on land that is now worth millions, and resent them a little bit while still managing to find them completely adorable.
Capitol Drive-In
Pretty self explanatory, the Capitol Drive-In located in San Jose is one of the few remaining drive-in movie theaters. Go here to relive memories of making out in your parents’ Toyota Camry back in high school. Because if you work in tech in Silicon Valley, you were DEFINITELY cool enough to make out in your parents’ Camry back in high school.
Additional bonus points goes to this place for showing that hot dog jumping into a bun thing from the movie “Grease.”
The New-School Spots
San Pedro Square
Ever since this place opened in 2012, it’s been my go-to place for kicking it in San Jose. Lots of solid places to grab food and drinks, all in a walkable hipster food court type of location — what more could you ask for? The San Pedro Square Market Bar is a particularly good spot to go people-watching while sipping a drink.
Silicon Valley Capital Club
The Capital Club in downtown San Jose seems like (to steal a well trod analogy) a “poor person’s idea of what a rich person is like.” The gaudy purple walls, lush sofas, and ornate lighting fixtures dangling from the room evoke Vegas opulent living at its most excessive. Couple that with a menu that includes the likes of filet mignon and lobster, gorgeous views overlooking all of downtown San Jose, and you get the perfect spot for a certain kind of Silicon Valley date. Go here to warm up to your Fifty Shades of Grey fantasies.
Fujitsu Planetarium
For those of you who like to get blazed on your date, the Fujitsu Planetarium on the campus of De Anza College has a Pink Floyd show every Saturday. It’s the perfect place to fall in love, get blazed, and learn about science, all at the same time!
The Pre-work Hike Date
With the growing popularity of dating apps, the typical afternoon coffee date or evening drinks have become so common that they’re… well, pretty boring. At one point, I became so bored with that same old routine that I started mixing in early morning dates. It’s different from the same ol’ routine, and if things go well, your date will think about you for the whole rest of the day. One idea is to go for a hike along the Stanford Dish to see the sunrise, followed by grabbing breakfast at the Stanford Barn.
Overall, you don’t have to go to SF
Most people think Silicon Valley is a mass of suburban strip malls and tech offices without a lot of places for a romantic night out, but between the plethora of dining options and the unique entertainment, there’s still a lot of cool places down in South Bay!
About the Writer: Leon D worked in technical, marketing and sales roles in various tech companies. Passionate about GPU design, Blockchain, and Machine Learning. Avid surfer. 6ers fan.
About the Editor: Jason Weber is a Director at Wiseflow Enterprises. He’s built several profitable companies in SaaS, IT Consulting, and Corporate Housing, and has worked at top tech firms including Amazon, Hewlett-Packard, and Intel. He holds four issued patents and is passionate about practical Zen, the Flow State, high-tech, and the hustle.