Seattle - First date tomorrow night
Hale's Ale dinner and try the sampler after
The Jolly Rodger Tap room- it is pirate themed and has sliders that you can order custom toppings for
Jillian's to play arcade games
El Chupacabra for a fun expereince
Shorty's for games and drinks
How about the 74th St. Ale House or the Columbia City Ale House. Or a great pizza place: Via Tribunali on Capital Hill, Queen Anne, or Fremont, or Serious Pie (downtown), Stellar Pizza (Georgetown) or La Vita y Bella (Belltown), all places I love.
A second option would be a fabulous happy hour, like Brasa, Taberna de Alabardero, Tango, or the latest review, Sazerac. You can't go wrong! Have fun!
What kind of atmosphere are you going for?
For laid back, I like zoogrrl's suggestion of 74th St Ale House or Via Tribunali. VT would be my pick of the 2 because it has a little more atmosphere, and you can share pizzas (if you're comfortable enough on a 1st date!).
How about Quinn's? A little hip, good bar, interesting food, not too pricey.
Another option could be Ocho. Doesn't hit the wallet too bad, but it LOOKS like it would. Interesting food and good bar here too. Tables are jammed close together which could be either annoying if you're on a bad date, or great if you're on a good one. =P
Building on maybelle's idea for a reasonably-priced place that looks expensive, my current favorite is Olivar in Capital Hill. You could share 2-3 small plates (which really aren't that small), enjoy a glass of wine each, and walk out the door for around $40. I definitely recommend getting a reservation. There's closeby options of drinks at Poppy or a movie at the Harvard Exit.
806 E Roy St, Seattle, WA 98102