Great Third Dates

BY THE THIRD outing, sparks are flying, and an activity date works well to keep the conversation going. “People may feel more at ease if they are doing a task while communicating,” says Allen, who adds that the mere act of planning ahead says a lot about how much time you may or may not put into a relationship. We’ve made it easy with these surefire dates.

Test out the endorphins-as-aphrodisiac theory by tackling the strenuous, seven-mile-long Dog Mountain Trail in the Columbia Gorge ( Afterward, order up Black Cherry Stout for two at Walking Man Brewing (240 SW First St, Stevenson, Wash.; 509-427-5520). But best to keep it to just one pint each to avoid a crawling-man situation.

Grab sandwiches from Elephants Deli (115 NW 22nd Ave; 503-299-6304) and spend some quality time at the Oregon Zoo (503-226-1561) with Packy and his crew. After all, there’s no such thing as an awkward silence when you’re animal-watching.

Take that trip (finally!) on the Portland Aerial Tram, and follow up your high-altitude adventure with a stationary assessment of the city’s skyline from the Portland City Grill (111 SW Fifth Ave; 503-450-0030). The panoramic view makes these environs the city’s best bet for creating your own Sleepless in Seattle moment.

Great Fifth Dates

SO YOU’VE ALREADY discovered a mutual love of French food, The Big Lebowski, and flipping through old vinyl. But are you just as smitten when he’s rocking sweats at 8 a.m. on a Sunday? A fifth date is the ideal opportunity to discover if you share core values, says Allen, and doing a community service project can help you get beyond superficial likes and dislikes. (A date where we can wear sweats? We think the Dude would approve.)

Show off your power-drill prowess while volunteering on a Habitat for Humanity project (503-287-9529; Able-bodied folks are always in demand to help build homes throughout the Portland metro area. (And if you’re lucky, your date will be clad in short shorts and a low-cut V-neck.)

Get behind the wheel and deliver food for Loaves and Fishes (503-736-3625;, which has 35 meal sites around town and is in constant need of good drivers. Plus, when you pore over a street map together, your heads—hence your lips—are that much closer.

Join a beach cleanup effort with SOLV (503-844-9571;, which has already removed more than 111,000 pounds of litter from Oregon coastline. Who was it that said, “The couple that picks up beach trash together, stays together”?