Sameera Sullivan is always looking. She looks at Zupan’s. At Whole Foods. At the bar at the Pearl District P. F. Chang’s. She is looking for love—but not for herself.

“Hi,” she tells the unsuspecting organic shopper or corporate cocktail consumer. “I run a matchmaking service for elite business professionals. Are you single?”

The former executive headhunter (defense and aerospace, in Texas) thinks Portland’s low-blood-sugar dating scene needs a boost. “Everyone is so passive,” she says, echoing many a girls’-night-out lament. Her two-year-old firm, Lasting Connections, aims to hook up the city’s untethered professional class and elites. Clients’ incomes, she says, run from $70,000 a year to “millions.”

Sullivan recruits wherever unattached high achievers can be found. She cold-calls people on LinkedIn and stations herself at Starbucks, Peet’s, and, yes, P. F. Chang’s. “It’s a good place,” she says. “Everyone there is gluten-free, single, and works a lot.”

To see what she offers lonelyhearts, Portland Monthly sent Sullivan a 26-year-old white male guinea pig: me. Being a writer, I fall outside of Sullivan’s economic catchment zone. But we agreed the experiment could be mutually beneficial.

Sullivan’s clients can avail themselves of three service packages, from “Basic Executive” to “Black Diamond Concierge.” (Sullivan won’t divulge the exact fee for the latter publicly, but rest assured it is substantial.) The services rendered can stretch on for an entire year. All the packages involve a Sullivan-directed total makeover of look, wardrobe, and even attitude. That’s what I got. 

Improvement was not hard. I met her wearing my usual. She told me I needed immediate attention across the board. My dirty P. F. Flyers sneakers were “not working.” My hair looked like I’d  “just rolled out of bed.” My pants were dirty. I was a disheveled mess. Undatable, by Sullivan’s standards. 

A new upscale matchmaking service, Lasting Connections, promises over-scheduled, under-cuddled Portland professionals a new lease on dating life. We sent disheveled writer Sam Coggeshall to find out what that really means.

She took pity, and command, with the no-nonsense air of a person in the business of providing opinions. Sullivan ordained a new haircut (a Channing Tatum–esque ’do). We went to Avalon Antiques and Vintage Clothing and picked out a new look, composed of a blue ’60s blazer with gray stripes, a button-up shirt, dress pants, and shoes. A gold lapel pin and cotton handkerchief pulled it all together. Sullivan patrols salons and clothing shops with the sharp eyes of a huntress. She also advised me on how to compliment women without “crossing the line,” which I don’t think was a problem. But maybe this date whisperer sensed something about me of which I’m not aware.

So? No dates yet. Perhaps I need to step up for the Black Diamond treatment Sullivan lavished on one dude, described in a recent press release, for whom she collected online applications from interested women and organized a ladies’ night of 100 to narrow the selection. 

But, hey, there’s nothing like a vintage blazer to give a guy more confidence. And for Sullivan? Business is good. She’s expanding to Seattle, San Jose, and Houston. “I feel like this is what I am meant to do,” she says.