I have a nice ass.

At least that’s what Alma Avery Rubenstein, professional dating coach, tells me when she makes me stand up—mortified—in Sip & Kranz Café and Wine Bar so she can give me a thorough once-over. “Your skirt could be tighter,” she says. And I need to stand straighter. “You want to project an attitude that says, ‘Check me out.’”

Clearly, “tactful” is not a word you’d find in a personal ad for Rubenstein. But “nervy” is. For the past six years, the petite 40-year-old—who has appeared on The Bachelor and Blind Date—has run a professional dating business in Seattle, making a living out of telling people what they’re doing wrong (and right) when it comes to love: too much nose hair, too little cleavage, way too much cologne. Rubenstein personally meets and screens every potential participant for her speed-dating sessions. After all, when your reputation is on the line, you don’t want Johnny Close-Talker showing up.

“I want to ensure quality,” Rubenstein says. “Meaning, I want to weed out the crazies.” 

Now the sharp-tongued brunette has relocated her advice to Portland, where she’s running standing-room-only speed-dating parties and flirting classes at Bridgeport Brewpub, Candy, and Fenouil. So far, Rubenstein hasn’t been wowed by the state of our singles scene, despite its potential. While we have no shortage of people on the hunt—according to the US Census Bureau, nearly 60 percent of Portlanders are unmarried—she is frustrated by the collective lack of initiative. She hasn’t heard one good pickup line in the nine months she’s been here.

“Women could walk around naked in this city and not get noticed,” Rubenstein says.

But it’s not all the fault of those Portlanders with Y chromosomes. She notes that women here seem to be petrified of rejection, too. And, a few minutes into our $125-per-hour, one-on-one lesson in flirting, she’s deduced that I am Exhibit A. So she gives me homework: I have a week to give my phone number to three men. All in a night’s work for some, perhaps, but for a woman whose own mother had to actually pay her to go out on a date, it’s excruciating.

For six days, I roam Safeway, scour the gym, and eye men in cafés. But the best I can manage is a quasi-flirtation with a Pizza Hut delivery guy in the elevator.

“Typically Portland,” Rubenstein scolds at our next lesson. “If you want to make changes in your life, you have to do something different.”

So we head to Jamison Square for some training: role-playing. She plays the man. “Nice shoes,” is the best line I can muster. The master sighs, then takes over my role.

“Here,” she says, handing me her business card. “I think you dropped this.”