European Vine Selections, aka "the wine shop on 15th," has been an unintimidating resource for good wine (with lots of bottles under $10) on Capitol Hill for 25 years, and every Friday they host a free wine tasting from a different region. One person you may find pouring is EVS partner Doug Nufer, who is a civic treasure of both friendly, low-key wine knowledge and experimental writing. Free.
Geeks Who Drink is a company that hosts trivia quizzes at different bars every damn day of the week, here in Seattle and all over creation, usually free (except for bar owners, who pay a "reasonable" rate). Starred for geeks who drink who like pub trivia.
Literally millions of happy hours are taking place around Seattle RIGHT NOW. One is highly likely right under your all-too-sober nose: Find out where it is here (for iPhone users) or here (for Luddites). Food! Drinks! Cheapness! Yes! CHEAP!.