San Jose, CA Dating Guide
What’s sweeter than an ice cream date? Cauldron Ice Cream makes delicious, homemade, all-natural ice cream in small batches. They serve up unique flavors, with new ones hitting their menu every few months, so you can revisit this adorable first date spot together again and again.
Tostadas $$
Brothers Alex and Victor Garcia were inspired by their upbringing to bring authentic Mexican American flavors to diners in an inviting atmosphere. Low lighting and beautifully plated food take this family restaurant to the next level, making it the perfect place for a date night.
Located in the heart of the city on Santa Clara street, Hom Kitchen serves up wholesome, delicious Korean favorites. The San Jose is location is open late, so you can chat here on a lunch date, or stop by for a quick bite after a night on the town together.
K Cafe Patisserie & Tea House $$-$$$
Chat with your date over lunch in this adorable vintage-chic restaurant. The menu at K Cafe Patisserie & Tea House features unique Asian-French fusion creations for brunch, dinner, and dessert. Take in the stunning floral decor in the dining room, or relax on the Parisian-inspired patio.
Miniboss $$
Miniboss is the place to go to spend all day beating each others’ high scores on dozens of arcade games. The bar has something for everyone, too, with a drink menu of signature cocktails and vegan and gluten-free food options to snack on between games. Apply cheesy jokes about finding your “player two” sparingly.
Nothing creates that spark quite like laughing together, so why not head to the funniest spot in town? ComedySportz San Jose hosts a variety of live performances, including sketch, improv, and stand-up acts. Grab a beer and a front-row seat, and get ready to laugh!
Ashy Aromas $$-$$$
This place is like Build-A-Bear for candles. Ashy Aromas offers several different candlemaking experiences. Pick your shape, color, scent, and add accessories for a personal touch. At the end, you’ll have a tailor-made new candle, perfect for a candlelit second date!
If you’re looking to show your date something completely one-of-a-kind, look no further than this San Jose landmark. Explore the world’s most unusual and sprawling mansion where for four decades the construction seemingly never ceased. The Winchester Mystery House is an architectural wonder spanning 24,000 square feet, with 10,000 windows, 2,000 doors, and 160 rooms to stroll through together.
Want to do something a little steamy on your first – or fiftieth – date? Head to the Bay Area Glass Institute, where they offer both introductory glass experiences as well as studio classes for those looking to get a little more serious about this red-hot hobby.
At the West Wind Drive-In, you and your match can snuggle up in the front seat to enjoy a double feature. Head over to the arcade between films, or grab some popcorn to share at their fully stocked snack bar. Drive out to the drive-in for midnight screenings of major releases, and a mix of contemporary and classic films.
Palermo $$
Head to Palermo to enjoy some of San Jose’s best Italian food on the banks of the Los Gatos Creek in the historic cannery district. Order drinks and split a pizza, or kick the romance up a notch and have dinner on their stunning covered patio.
San Jose Municipal Rose Garden $
Just picture it – walking hand in hand with your date through lush greenery and gorgeous flowers, utterly blissful. Named “America’s Best Rose Garden,” the San Jose Municipal Rose Garden is a year-round urban oasis. The rolling green lawns and thousands of breathtaking blooms make this the perfect place for a picnic. What are you waiting for? Get outside and smell the flowers!
Overlooking the Santa Clara Valley, The Grandview Restaurant gives diners the definition of dinner and a view. Enjoy impeccable service and an incredible meal made with farm-fresh ingredients at this classic steakhouse. The Grandview’s house-owned farm is right across the street, so the kitchen creates new and unique seasonal menu items, all year round.