Dating Scene

Savvy Sexy Single

A three-step guide to getting exactly what you want.

By Stacey Wilson May 19, 2009 Published in the May 2008 issue of Portland Monthly

LIFE CAN BE TOUGH for the unattached. You know, leaving the “Plus One” box empty on a wedding invitation, dining out with a copy of Eat, Pray, Love as your only companion. On the other hand, until commitment calls you to the other side, you can revel in the fact that you live in Portland, a place where the number of singles per capita bests the national average. Of course, just because there may be more unwed men and women out there, that doesn’t mean it’s any easier to catch them. Which is why we’re here to help. We’ve wrangled relationship experts to tell us what singles are doing right and wrong in each of the three phases of single life—looking, dating, and committing—and have wracked our brains for strategic pickup spots, dates that are sure to score points, and ways to seal the deal. Will 2008 be the year you surrender your singlehood altogether? Perhaps. But if it isn’t, go forth as a wiser single and gloat to your married friends about how much fun you’re having. For the first time, you might actually mean it. 

AT SOME POINT, every single has played “Spot the Empty Ring Finger.” And given that the Census Bureau counted 90 million singles in the United States in 2006, you’d think it would be an easy game to win. Apparently not (at least not if the 54,000 Portlanders with accounts are any indication). But merely looking and hoping isn’t going to net you much more than frustration. To ensure you get exactly what you want, you’ve got to be more strategic in your search (hint No. 1: skip the bar). Our experts tell you how.

THERE ARE NOW more than 1,300 U.S.-based Websites dedicated to creating cyber love connections. Yep, online dating is here to stay. And while the stigma may be gone, making your profile pop gets harder with each new member. Galen Buckwalter, the head of research for, says just a few tweaks to your online-dating approach can mean the difference between time wasted or time well spent. “A ‘glamour shot’ is nice,” says Buckwalter. “But a variety of photos is crucial.” After all, there’s probably more to you than the 20 pics of your last camping trip suggest, and if you’re not a hardcore outdoorsman, you’re sending the wrong message anyway. As for the profile itself, brevity is key. And remember, even a typo can be a deal-breaker. “It amazes me how many people don’t spell-check their profiles,” says Buckwalter. When you do connect with someone, it’s wise to wait at least a week before meeting to ensure enough getting-to-know-you time. “But you don’t want to correspond too much beforehand, as that creates feelings prematurely,” he says. “Then it’s harder to say no to a second date.”

THE NATIONAL DATING SERVICE It’s Just Lunch has set up over 1,000 bar-weary Portlanders on daytime dates with like-minded singles, all to the tune of a $1,600 annual membership fee. (Ouch.) There’s no guarantee that all that dough will net you a relationship, though, let alone an enjoyable afternoon. So if forking over two months’ rent to get a date isn’t your style, join one of these groups, where meeting someone who shares your passion for, say, planting trees is just a bonus on top of doing what you already love.


THE GAME Working up a sweat with Recess Time Sports League, 503-381-5056

THE PLAYERS Twenty- and thirtysomethings who take kickball, dodgeball, and bowling as seriously as the pitchers of Pabst that follow each game

THE SCORE Nothing says "I think I like you" like a big rubber ball to the chest. Except maybe buying your opponent a beer at Recess Time’s post-play parties, to which all of the league’s participants are invited. In fact, Recess Time’s founder, Colleen Finn, 29, met her girlfriend, Kim, on one of the league’s kickball teams, the Mt. Hoodlums. "If you can come, sweat, and still look cute after the game, you’re pretty much set," says Finn.


THE GAME Getting down at Tango Berretín, 503-771-7470

THE PLAYERS Novice and seasoned hoofers, from teenagers to the golden-years set, looking for partners in dance, romance, or both.

THE SCORE Alex Krebs doesn’t like to cheapen the tango by calling it a "sexy" dance. "It’s more sensual than anything," says Krebs, 30, the studio’s owner and instructor. (That sounds promising.) Drop in on a Friday night for a $10, one-hour lesson and stick around for the milonga—the 30-person group dance session that follows—and see where your rhythm takes you.


THE GAME Saving the world with Oregon Sierra Club, 503-243-6656

THE PLAYERS Idealistic grad students, do-gooding yuppies, and divorcés looking to get back in the game, politically and otherwise

THE SCORE Exercise your green thumb and plant trees with America’s oldest environmental group. Or simply mingle with other enviro-leaning singles at Activist Night on Tuesdays, or monthly “Sierra Club and Beer” events at the Goodfoot Lounge. “There is a lot of love-budding in nature,” says Nat Parker, 29, the Portland chapter director. And apparently between the people saving it, as well.


THE GAME Heating it up at Oregon Culinary Institute 503-961-6200

THE PLAYERS High schoolers to senior citizens, and all the people in between who are hoping to spice up their routine.

THE SCORE With course names like “Thai Me Up,” no unattached foodie should miss a chance to get schooled in one of this cooking school’s 90 classes. Program director Kevin Richards, 35, says the “intimate kitchen space” creates a welcoming environment for folks who show up solo. And the five-hour sessions provide plenty of time to whip up conversation.

THINK YOU’RE TOO busy to look for love? From your morning commute to your evening spin class, the daily grind offers ample opportunity to spark conversation with strangers. “The key is to employ self-deprecating wit with a dash of harmless flirting,” says Portland Monthly consulting editor Bart Blasengame, 34. Blasengame offers these four reliable icebreakers that helped move him off the singles market and into a relationship. (Sorry, ladies.)

On the bus "I’m totally stumped on this crossword. Do you know a three-letter word for ‘domestic feline’?"

In line for coffee "It’s inspiring to see someone order her coffee in under 15 syllables. I can’t seem to do it in under 20. What’s your secret?"

At the dog park "There’s nothing like scooping up after a dog to keep the human ego in check, eh?"

At the gym "I’m impressed that you’re able to run for 50 minutes on Level 7. Are you training for the Portland Marathon, or just a far superior athlete than I am?"

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.

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”? 

COMMITMENT DOESN’T JUST mean a trip to the altar anymore. According to the National Center for Health Statistics, 5.5 million unmarried couples have committed to cohabitation. No matter how you define it—matrimony, living together, or simply clearing space in the bathroom drawer—commitment can be scary. Even so, bidding the dating world farewell can be the most rewarding phase of adult life, especially when you’re armed with the tools you need to make a smooth transition from merely dating to utterly devoted. And we’ve got them all right here.

Couples Tips —SET THE RULES

PORTLAND-BASED marriage and family therapist Brian “Dino” Paris, 46, has counseled hundreds of couples grappling with commitment issues. He’ll be the first to tell you that there are no guarantees that any commitment will lead to a life of fulfillment and bliss. Still, you can vastly improve the odds that yours will, with these four tenets.

1 Be selfish, in a good way. Shortly after he started dating his wife 16 years ago, Paris recalls that she asked him what he calls “that difficult question”: What do you really want? (He didn’t know.) Putting oneself first is often considered a negative trait, but if you know what you need and don’t settle for less, your odds of relationship success markedly increase.

2 Make rules and stick to them. Establishing rules early on can prevent a lot of unnecessary heartache. “I have a lot of young couples come in, and the guy says, ‘I want to be able to glance at a pretty girl on the street without getting hit on the arm,’” says Paris. “It sounds silly, but having a formal agreement to ‘look but not touch’ is very healthy.” Agreeing on emotional rules (and by “rules,” Paris doesn’t mean issuing edicts) creates a sense of security and decreases the likelihood of your partner committing the ultimate rule-breaker: infidelity.

3 Duke it out sooner rather than later. Don’t wait to address issues in your relationship until you’re 10 years into a marriage or partnership; at that point, resentment can become unmanageable. So make a date with the couch—a therapist’s couch, that is. “All commitment issues can be traced back to our upbringing and family life, and can be helped through therapy,” says Paris. “These are extremely normal, extremely common scenarios. We all need help sometimes. There is no shame in seeking it out.” And if your mate isn’t willing to commit to counseling, then that in itself speaks volumes about her commitment to you.

4 Accept uncertainty. You may want to feel that love is forever, but no commitment is a surefire insulator against loss or a broken heart. “This gets into spiritual territory,” says Paris. “But if we look at our fragile existence as humans, commitment is an illusion. If each person accepts that, in the end, they can only really count on themselves and their beliefs or faith, it can actually strengthen a partnership.”

Couples Dates — SET THE MOOD

ENTERING FULL-ON “couple mode” not only means you have license to engage in spontaneous PDA, but also that you can, and should, step up the romance factor. These two nights away are guaranteed to keep the butterflies fluttering.


NOTHING SAYS “We’re officially together” like dropping $200 on a steak dinner. And there’s no better place to tuck into a filet than the thoroughly hedonistic steak house El Gaucho (319 SW Broadway; 503-227-8794). With its suited-up waitstaff, live Latin guitar music, tableside food preparation, and cavernous booths, the downtown supper club is the Rose City’s unofficial haven for lovebirds with deep pockets (or at least very good credit).

After the complimentary fruit-and-cheese plate has been cleared, it’s a short walk to the Heathman Hotel—voted one of the “World’s Best Places to Stay” by Condé Nast Traveler—where your night of excess continues with the hotel’s pleasantly over-the-top “Romeo and Juliet” romance package. For about $280 per night, you and your sweetie can lounge in a luxury suite adorned with candles, sparkling wine, and chocolate truffles (503-241-4100; The next morning the love continues with breakfast in bed: fresh-squeezed orange juice, croissants, and coffee. Of course, you should feel free to skip the continental spread and hang the “Do Not Disturb” sign on the door instead.


WHEN YOU’RE IN that twitterpated frame of mind, it’s easy to get sucked into a lazy Portland weekend of brunching, watching DVDs, and walking around the neighborhood. But a day and night out of town can do wonders for bolstering romance. For roughly $70 per person round-trip, let Amtrak ( shuttle you north for a day and a night in the Emerald City. Book a room at Seattle’s ultra-romantic Inn at the Market (206-443-3600;, situated just feet away from Pike Place Market. Nearly all the suites in this 70-room boutique hotel have views of Elliott Bay, the perfect backdrop for that in-room couples massage.

Once you’re loosened up, head across the courtyard for dinner at Campagne (206-728-2800; This famed bistro has seen more than its share of marriage proposals, and it’s easy to see why: Its expansive dining room windows overlook the market and the bay, a picturesque complement to rustic French dishes such as lamb shoulder marinated in anchovies and garlic, and salt cod and curry fritters with aioli. By the time the gâteau au chocolat has arrived and your chardonnay buzz has melted into an all-consuming stupor of satisfaction, you may find yourself ready to say the “L” word. Or at the very least, “I’m glad I found you."

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