The airport which the city gets its handle from, Portland International Airport actually has some great dining, including The Country Cat, Blue Star Donuts, Tamale Boy, and Laurelwood, and it makes for some of the best people watching in town. And hey, if the date is going atrociously, you can always excuse yourself and fly far far away from here.
On the second Thursday and last Wednesday of every month Ground Kontrol puts its games on free play and charges a $7 cover, so you can finally beat that last level of Double Dragon with your date without breaking the bank. Then, you can spend the rest of your budget on cheap drinks and even cheaper hot-dogs, although it’s better to head a block away for tacos and tequila at Mi Mero Mole.
Flip through some books together in the Rare Book Room at Powell’s Books, or just wander the stacks together. Then, head across the street to Sizzle Pie for a slice and a drink. Just don’t do it in reverse order -- the staff at Powell’s frowns on getting grease stains all over the rare books.
You can find a Geeks Who Drink trivia night every night at the week, hosted at various bars all across town. You’ll be able to impress your date with your brilliant knowledge of state capitals and facts about the show Airwolf (1984-1987), and all it will cost is the price of whatever drinks you feel will enhance your trivia skills.