IN 2000, 44 percent of Americans were “unmarried,” according to the U.S. census. This means staying single is no longer merely a status, but a lifestyle choice. With this lifestyle comes the freedom to play the field. Of course, it pays to have a game plan, so we wrangled a dating guru to give us the lowdown on chemistry, consummation, and whether Portland’s male population is too shy, or just highly evolved. And because dating should be fun, we offer up nine outings for the first rendezvous and beyond. The only way to lose at this game is by not playing at all.

Great First Dates

IF THERE IS one rule for a first meeting, it’s to keep it short. “You can sense pretty quickly if you like someone, so you don’t want to be stuck on a long date if you aren’t interested,” says Allen. Which is why meeting for coffee is an ideal first date—and that’s not coffee with four shots of Baileys. “Getting drunk together often leads not just to sexual, but also emotional promiscuity that you may question in the morning,” says Allen. Here we offer three ideal venues for some innocent first-date java.

2511 SE Belmont St; 503-230-8914
Atmosphere Formerly known as the Shop, this cute little house-cum-coffee-shop is Southeast’s premier den of mellow. (Ben Harper played on low volume is about as raucous as it gets.) The peaceful and toddler-free environment makes for a low-key first meeting over lattes, green tea, or a spirited game of Trivial Pursuit.

Intimacy factor Between the coffeehouse’s fireside couches and spacious outside patio, it’s easy to find a quiet, private nook to swap online-dating horror stories.

The next step There are at least three Thai restaurants just blocks away. So upping the ante from coffee to curry is easy—after you’ve scored your last piece of Trivial Pursuit pie.

911 NW 14th Ave; 503-546-5919
Atmosphere Art students and freelance writers politely tap away on their laptops in this spacious, conversation-friendly Pearl District hangout. The extended hours—it’s open daily until 10:30 p.m.—means that a good first date can last long into the night.

Intimacy factor Settling into one of the comfy leather couches will make your chat feel less like a job interview and more like a romantic interlude.

The next step Tucked between Northwest Portland and the heart of the Pearl District, the café is a short walk to the date-friendly crêperie Le Happy and to PNCA, whose galleries are free and open to the public every day until 9 p.m.

4001 N. Mississippi Ave; 503-284-8928
Atmosphere It’s a zoo in the mornings and on weekends, so if you’re heading here on a first date, best to come sometime after 3 p.m. on a weekday. By then the unemployed graphic designers have headed home for the day, and you’re left with the best place to people-watch in the neighborhood.

Intimacy factor It isn’t particularly sexy or cozy, but the constant bustle may require you to squeeze in closer to your date, creating a certain “we’re in our own world” kind of mood.

The next step You can’t go wrong with a stroll up and down N Mississippi Avenue, especially if you end up at the delightfully romantic and low-lit Lovely Hula Hands for dinner.