Show 'em your art and soul
Street festivals occur in Oakland throughout the year, but the Art and Soul Festival in Downtown Oakland is one of the largest. Thousands of people head Downtown each summer for a weekend of live music, multicultural food, art, and excellent shopping. Take BART straight to the event, or pedal over on a bike -- the festival offers free attended bike parking. If the chemistry is right, this date could last all day.
Get tilted at Hi-Life
Keep it casual way late into the night at this bar/pizza parlor/pinball haven on Broadway at 15th St. Order up a couple of beers and a few New York-style slices, then head upstairs with your date to tilt some machines (or don’t, some folks are real serious about playing fair). Hi-Life (also called Five10 Pizza) has a row of old-school and new-ish pinball machines, along with some older favorites such as Frogger and Ms. Pac-Man. It's open 'til midnight every night except Saturday, when you can play until 2am, so bring a roll of quarters and start a pinball competition. Winner pays for the next round.