3) The Ferry Building, San Francisco (Embarcadero)
It seems nearly impossible to have a boring date at a marketplace that offers so much. Try Hog Island Oyster Company for a super social happy hour Monday through Thursday, or meet up on a Saturday morning for celebrity-chef-spotting at the farmers’ market. Grab a meat cone or a satisfying sandwich from Boccalone or a loaf of bread from Acme and a wheel of Red Hawk from Cowgirl Creamery to make your own, then head to the dock to watch the boats pass by.
4) Brazen Head, San Francisco (Marina)
One of San Francisco's best late-night restaurants has flown under the radar since it opened in 1980. Belly up to the bar for a classic gin martini from a charming curmudgeon of a bartender and enjoy it with a plate of oysters and a spot-on French onion gratinee soup. A petite filet, some shrimp scampi, and the flattering dim light of the tiny dining room add up to romance galore. The best part? They serve dinner until 1am.
5) Bar Bocce, Sausalito
The newest addition to Sausalito’s tourist-friendly and locally-beloved food and wine scene is an idyllic spot for a first date. Watch the sun set over the harbor from any of the outdoor couches or tables surrounding the fire pit, or ignore the natural beauty in favor of athletics as you toss a bocce ball forward and a glass of wine back. Though the food is secondary to the setting and the innovative wine-cocktail list, Bar Bocce is absolutely worth a visit for a first date--even if it's just with a friend.
6) Sorella Caffe, Fairfax
Classically Fairfaxian-casual, Sorella Caffe has a skilled, low-key staff and solid Italian food with flair. Special touches like a live piano player, a round windowed dining room and a fireplace that makes diners feel as though they're enjoying their gorgonzola ravioli in a toasty, warm yurt. Sorella is a comfortable spot to get to know someone while enjoying a little whimsy-- a giant communal wheel of Parmesan cheese arrives as the menus do and diners are presented with a bowlful of gummy bears to dig through while perusing the dessert menu.
7) Picco, Larkspur
Let's face it--you can't go wrong taking a date to ANY of Bruce Hill's restaurants. Bix, Zero Zero, and Pizzeria Picco are all excellent establishments on their own merits, but there's something about Picco that is so cozy and inviting that it's hard to imagine any first date that takes place here not being a success. After a dinner of Hill's made-to-order risotto of the day, paired with one of the restaurant's signature cocktails, take a stroll through downtown Larkspur to enjoy the fresh Marin air.
8) Underwood, Graton
Sure, it's a drive from just about anywhere in Sonoma, Marin, or San Francisco Counties--unless you happen to be one of the 1900 people who live in Graton--but the Underwood Bar and Bistro is worth a trek of any distance to eat chef Matthew Greenbaum's food while sitting quietly amongst the wine country movers-and-shakers who come to their hometown restaurant for a little slice of sophistication. Sharing several small plates of tapas and some innovative cocktails like a French Martini is a great way to break the ice. And hey, if the date goes REALLY well, you can breakfast at Greenbaum's Willow Wood across the street...the next morning.
9) Scopa, Healdsburg
In a town where antiques and San Francisco Marina-district overflow comprise more of the population during the summertime than native Healdsburgers do, Scopa is a bastion of good, homey food with a hip atmosphere that caters to tourists and locals alike. Scopa is right on the town's central square, and a stroll around the grassy park and a little window-shopping while you wait for your table sets the tone for a casual yet intimate evening. Don't miss Nonna's chicken, a recipe handed down from NorCal local chef Ari Rosen's grandmother. A perfect mix of local and carefully-selected Italian wines are de rigeur.
10) Diavola, Geyserville
The more casual "little brother" of the former Santi (R.I.P.), Geyserville's Diavola focuses on turning basic local ingredients into the most delicious pizza, pasta, and housemade salumi and sausages. In addition to a 'dine-at-the table' date, Diavola offers a plethora of options for a picnic date. Grab some homemade pickles and pate from the take-out case, and enjoy your meal outdoors with a bottle of local wine at any of the dozens of wineries within a 10-mile radius.