A quarter of a million dollars is a lot to pay for a dating service. But Selective Search is not a dating service. Rather, founder Barbie Adler and her team of 20 matchmakers conduct exhaustive, highly customized searches to find love for people with high standards and far more money than time. 

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Adler, a former executive recruiter, founded Chicago-based Selective Search in 2000. Fees start at $25,000 (that will soon go up) and in some cases can reach into the six figures, depending on factors like a search's duration and whether Adler handles it personally. The company, which employs more than 40 people, has annual revenue north of $10 million. It claims an 87 percent success rate, which works out to more than 4,000 happy couples--1,800 of them married--to date. Roughly a third met "the one" on their first introduction.

The process begins with a tell-us-everything intake interview: 15 pages of questions that assess not just what clients want for the future (interests, values, desire for family, deal-breakers) but also how their attitudes are influenced by their past relationships. From that input, the company produces a document detailing more than 100 personal, professional, and social preferences specified by the client. Those criteria are matched against Selective Search's database of more than 250,000 eligibles. They also go out to the company's 90 scouts--well-connected people around the country who shake their networks for promising matches in the client's designated regions. 

Potential matches undergo the same in-depth personal interviews as clients. Only those with the highest degree of compatibility are presented--in portfolio form--to the clients, who can choose whether to contact them. (The company thoroughly vets both clients and potential matches to weed out phonies and bad eggs.)

Selective Search doesn't just make matches; it also nurtures them. After every date, the matchmakers debrief both parties and coach them on improving the relationship going forward. That includes cluing them in on what their dates reported. "A lot of them don't think they need the consultative coaching," Adler says. "But once they hire us they don't want to make a move without knowing how they were perceived."

Love Story No. 1

In 2013 Brett, an entrepreneur with half a dozen companies under his belt, was in his late 30s, on the back end of a tough divorce, and sick of living like a hermit. Friend and family fix-ups failed. Dating apps disappointed. A friend researched other alternatives and suggested Brett sign up with Selective Search. Over the next 18 months Brett, who paid $250,000 for personal attention from Adler, went on dates with five or 10 women. Then he met Ashley, a fellow entrepreneur who "was as adventurous and energetic and independent as I was," Brett says. "I had found my partner in crime." The couple's wedding next month in Park City, Utah, will feature skiing, clay shooting, axe hurling, and Scotch tasting. Adler and two of her colleagues are on the guest list.

Roughly 30 percent of Selective Search's clients are women, who also make up the company's fastest-growing category. And it was listening to women that piqued the founder's interest in human dynamics. As a child, perched on the stairs of her family's home in the Chicago suburbs, Adler would spy on the marriage-enrichment groups--composed almost entirely of wives--that her mother, a psychologist, conducted in the living room. On the playground Adler honed her own interpersonal techniques, kindling grade-school romances by whispering to boys and girls about secret crushes she concocted.

After graduating from Bradley College in 1993, Adler embarked on a career in public relations, rising to lead the tech practice at Porter-Novelli. Adept at hiring talent for her team there, she jumped ship to an executive search firm. From her media-training experience, she had learned to coach a certain breed of powerful executive. Adler thought those skills would translate to the personal realm, which she considered potentially more meaningful.

With just her savings, Adler launched Selective Search out of her condo, meeting clients at their homes and offices. Her first clients came from the dense network of Chicago and Silicon Valley leaders she had developed in her previous career.

To build a database of potential matches, Adler immersed herself in Chicago social life. At parties and galas, benefits and art openings, conventions for young Democrats and young Republicans, there was Adler, chatting up people and handing out cards. She found the future wife of her first client at the Green Tie Ball, an annual fundraiser to clean and beautify the city. Today, people wanting to be considered as potential matches--known as affiliates--can sign up online, although many are still recruited at social events and charity functions. (Affiliates pay no fee.)

Love Story No. 2

When you're in your 50s and suddenly single in a Kansas town of just 10,000, the romantic possibilities are limited. So Jeff was intrigued when he saw an ad for Selective Search in an airline magazine on a flight to California in 2017. Recently divorced, the oil and gas industry executive got on the phone and within weeks received a profile of Brenda, a successful financial executive interested in sports, movies, and culture. They met at an Italian restaurant, "and I could tell within three minutes I would like her," Jeff says. "Best first date of my life." They were engaged in three months and married in eight. The icing: Brenda has grown children, which for childless Jeff meant "instant family." On Valentine's Day this year the couple will be swing-dancing to a 1940s-style band.

Not all of Adler's clients are as geographically constrained as Jeff. Often people with more than one home conduct searches in multiple locations. In around 35 percent of matches, one party or the other has relocated for love. That geographic diversity developed, in part, from Selective Search's most effective form of advertising: airline magazines. But after the Federal Aviation Administration loosened regulations limiting the use of electronic devices on planes in 2013, Adler found print ads less useful. Recently, she has shifted to a largely digital strategy on platforms like Google and LinkedIn. Also helping the company's profile: Adler's role as a consultant for the ABC dating show The Bachelor

But while clients may learn about a matchmaking service online, they don't want to use one there. Privacy is imperative for members of this demographic, who worry about protecting both their reputations and their personal data. Selective Search's scouts know only clients' first names; regular employees sign multiple confidentiality agreements. "To this date nothing has ever been leaked in terms of our marriages or clients," Adler says. "We are Fort Knox." 

Love Story No. 3

When they met in 2005, Adler thought Michael was "super cute." But the wealth management executive was a client. That meant a potential threat to her reputation. "I never wanted people to think I started this company to dip into my own candy jar," she says. Then Adler hurt her back and could not walk. Michael started calling and checking in on her. Eventually he sent her a letter offering to forfeit the remainder of his contract--Adler could keep the money--in exchange for one dinner date with her. "We went on a date and have been together ever since," says Adler, who asked to use Michael's first name only because she prefers to keep her married name private. "He is the best thing that ever happened to me."