Date Nights, Happy Hours, Fun Casual Dinner Spots, Places To Meet Singles In Silicon Valley, San Jose & Palo Alto, First Date Spots San Mateo, Hwy 1 Road Trips

Collectively, the area spanning Santa Clara to San Mateo counties has been dubbed Man Jose by various local and national media outlets. The male to female ratio in Silicon Valley can be devastating to men. Meanwhile, the cliche stereotypes and lack of choice can drive women to look elsewhere for dates. This is all the more reason to make sure you don’t mess up your dates if and when you do manage to get them. First impressions are crucial and you can’t expect to rebound from a bad first date when the ratios don’t favor your gender.

For the longest time, people would venture off to San Francisco for date nights but slowly but surely the South Bay and Peninsula has been added some great options to explore for day time activities or fun date nights. If you are creative enough, you can plan some great dates without having to travel to San Francisco.

As an online dating photographer and consultant, I have helped clients plan first dates to provide good first impressions. Here are a few of my favorite places around Hwy 1, San Jose, San Mateo, Menlo Park and everywhere in between. Scroll to the bottom of the page for San Francisco, East Bay, Marin, Napa and Sonoma date ideas.

Stanford Theatre, Palo Alto

Great, classic theatre showing timeless movies in a beautiful, rustic space. 

Fieldwork Brewing, San Mateo

Outdoor beer garden with various beer styles, benches, fire pits, bocce ball and more. 

Harley Farms Goat Dairy, Pescadero

Cheese, harissa, habanero jelly, baby goats – what else do you need? Make a day out of it with half and half soup from Duarte’s and fresh, warm olive bread from the market in town. 

Falafel’s Drive In, San Jose

One of my go-to spots when I am in town. This classic drive in is a favorite amongst locals and featured in Diners, Drive-Ins and Dives. Don’t forget the banana shake! 

Big Basin Redwoods State Park, Boulder Creek

One of my favorite hike in the Bay Area. Time it well for some amazing waterfalls.

Filoli Gardens, Woodside

Beautiful space, a bit pricey for admission but large enough to get a decent walk in. 

Santana Row, San Jose

Many places to grab a drink, share a bite or do some clothes shopping (nothing like getting a second opinion while shopping with a date). Head to the hotel for rooftop drinks or head to El Jardin for margaritas. 

Sandbox VR, San Mateo

For you gamer types, this is a fun spot to play games in a more interactive manner.

Selby’s, Menlo Park

One of the newer places to open up in the Peninsula, this old-school vibe with a modern twist is good if you want something more intimate and upscale without having to drive into SF.

Savanna Jazz, San Mateo

Casual live music spot with rotating bands. Great for those who want some tunes to listen to over drinks in San Mateo

Los Altos Stage Company, Los Altos

Local community theatre with rotating performances taking place in a small, former barn. With 99 seats there is no bad seat in the house. 

Bottle & Bottega, Campbell

Wine and painting in a fun, casual environment.

Library Bar, Rosewood Hotel, Menlo Park

Great for drinks, people-watching and hot messes.

Hedley Club, San Jose

Great for cocktails. This hotel lobby bar is casual, relaxing and great for getting to know each other.

Pigeon Point Lighthouse, Pescadero

One of the more picturesque lighthouses on the West Coast (alongside Point Arena).

Haberdasher, San Jose

Great cocktail bar, one of the few places where I would come for a drink in the South Bay. 

Stanford Architecture Tour

Create your own personal tour of the campus and finish it off with a picnic on the grass in front of the main quad. Clients get my list of favorite buildings, views and more. 

Trivia Night San Pedro Square Market, San Jose

Trivia night in a casual, social environment.

East Bay Date Ideas (Oakland, Berkeley, Alameda):

San Francisco Date Ideas

Sonoma + Napa, North Bay Date Ideas

About Eddie Hernandez 

Eddie Hernandez is a professional photographer specializing in natural, candid online dating photos. Featured in the SFGate, ABC7News, East Bay Express, Salon; contributor to Good Men Project, Plenty Of Fish and Meddle. In addition to photos, he provides guidance around app choice, bio optimization, messaging techniques, wardrobe advice and date ideas.

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For those of you who are remote or virtual dating help and are looking for an online dating profile critique you can read more about my services here.

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