The PI Wears Prada: One Woman's Midlife Career Change

When her job in real estate soured and her kids got older, Jeanene Weiner followed a dream: she started her own detective agency. Now this female private eye is living her dream.

By Paige Williams
Photograph: iStock Photo

On the Case

The doctor’s wife often slipped away in her Porsche to shop, play tennis, and visit friends. And when she drove away from the two-story colonial in a posh Atlanta neighborhood, a petite blonde in a Mercedes often followed stealthily. The blonde had secretly installed a global positioning unit in the Porsche’s dashboard; if she lost the car in traffic, she could track it from her computer. But the blonde didn’t lose her. Jeanene Weiner hardly ever loses anyone.

What Weiner found — and photographed — after only days of surveillance in 2003, was what she almost always finds: a lover, a tryst, the start of another painful end. The doctor’s wife had rendezvoused with her former college sweetheart at his house, at a museum, and at restaurants, where they held hands over glasses of wine. "When I told her husband, he was almost relieved, because she had convinced him that he was crazy for suspecting anything," Weiner says. "It still surprises me that so many people can outright lie about what they’re doing. I don’t know how they sleep."

The Path to Private Eye

Weiner, 44, is what some Southern women call darling: warm and attractive, with a lilting drawl, impeccable manners, and expensive tastes. These are traits that make her an unlikely, yet perfect, candidate to sidle up to a target couple in a bar, order a Chardonnay, and pretend to be waiting for a friend.

On any given morning, Weiner is at her desk by 8:30, assessing cases and deciding which investigator in her all-woman agency, Busted, to pair with which assignment. If the case calls for a nurturing mom, she sends Yvonne, a mother of two who brings brownies to the office. If Weiner needs someone to do surveillance in a rock club, Denise goes — she used to date a sound engineer. Back at the office, the debriefings — reports of hookups, hustles, and one particularly unforgettable 14-minute blowjob behind a suburban grocery store — often get as bawdy and loud as a late-night sorority party. "We like to call it Estrogenville," she says.

Weiner turned a keen eavesdropping talent into a career as a private investigator three years ago, joining the increasing number of American women making their livelihood in the field. The trade magazine PI estimates that 15 percent of the nation’s 60,000 private detectives are women, and most of those are over 40. Weiner found her place in that demographic almost by accident. After two decades as a real estate appraiser and landlord, the mother of Brittany, 18, and Brandon, 13, began to feel as though her life had become routine. "In the beginning, the rental houses that I had bought over the years kept me busy and satisfied," she says. "But after I fixed them up, all I would get were calls from tenants at eight a.m. saying, ‘My toilet is clogged.’ That got old fast." When one of the houses burned down after a young woman had left a candle burning, Weiner gave up her $120,000 annual income and sold the properties.

"I thought, ‘This is stupid. What if that girl had died?’" she says. "My kids were also getting older, and I wasn’t needed as much. I was craving a new purpose."

Leafing through a continuing education catalog one night, Weiner saw a course on private investigation. "Remember Moonlighting, with Cybill Shepherd?" she asks. "I always wanted to be her." She enrolled in the class the next semester, although rather than sexy stuff, Weiner studied esoteric differentiations between state and federal law: that you can videotape but not audiotape someone without their knowledge in Georgia and that, by state code 16-11-60, hidden cameras can not be placed where there is an expectation of privacy, such as a bedroom. "I loved it so much that I always came to class early," Weiner says. Half of the students were women, but Weiner likes to point out that only two of them became private detectives. "It was probably harder than they thought, or not as glamorous," she says. "It takes a certain kind of person to sit at a stakeout all day and not get discouraged." During downtime, she can’t read a book or even file her nails — her eyes must always be on the target.

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