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Depending how brave you are here are two of my favorite 'original date' places...
1) Finn Slough in Richmond. I'm shocked how few of people have ever heard of this place. It's essentially a bunch of Finnish people who have illegally built homes in a swamp in Steveston. They've sort of made it a tourist attraction (lots of written explanations and photo opportunities) in order to support their right to be there. Go there for some laughs and drop on over to Steveston for lunch afterwards.
2) Bingo. Likely neither of you really play Bingo which again, leads to lots of laughs and its easy to fill those awkward silent moments ("omg, what is a sputnik??"). There's a ton of bingo halls and they normally go all day, all day. Call ahead and see what time the sessions begin (normally 4 times per day, you buy a book of 15 games or so) or if they have 'drop in' (show up any time). It's cheap too- can easily be done for under $50 for both of you.
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