In one of the latest installments of Playboy.com’s new sex and relationship column, “Just the Tips,” a man writes in to ask how he can get over his anxiety about the size of his penis.
The expert, Katherine Cooper, responds with empathetic advice. “In my experience, the small penis casts a long shadow in the lives of many men. And as they say, to get rid of a shadow you must shine a light on all sides,” she writes.
Cooper tells him, “know your enemy” — and by that she means to avoid women who seek out the well-endowed. She also tells him to avoid scams. “Mail-order pills and ointments do not work. . . . Most people would rather date a small penis than somebody so easily swayed by advertising.”
Cooper, 28, a Boston native, is new to this job, but the transition has felt quite natural, she says. It’s her eclectic resume and upbringing, she believes, and then a winding career path, that put her in just the right place to be giving advice about the most intimate topics, particularly for an organization like Playboy that’s trying to update its website’s image.
“Being a person is difficult,” she says of the letter writers who seek her advice. “Being a person who has sex is even more difficult — but that shouldn’t be the case.”
While Cooper, who has been writing the column on Playboy.com since September, may see the logic of her professional evolution, it’s a safe bet that many others would not.
Cooper grew up in Newton with her parents, “Masterpiece Theatre” executive producer Rebecca Eaton and sculptor Paul Cooper. She spent her early years at the progressive Shady Hill School and went on to Milton Academy. After high school she decided to take a year off, working in a Kennebunkport, Maine, restaurant and then living in Rome for three months and India for five.
She earned a bachelor’s degree in performance studies and literary arts at Brown and then moved to Philadelphia, where she took a series of jobs, including being a personal assistant to a child psychologist, teaching kindergarten, and playing a German violinist in a post-apocalyptic theater piece.
Still in thrall to the theater, Cooper pursued a master’s in performance studies at New York University and faced a major career decision. “I had the opportunity to pursue a PhD, and I decided not to,” she says, explaining that she was not ready to commit more time to academics. “I knew I had other stuff to do.’’
From there, she took a series of jobs. She wrote for publications such as BOMB, a magazine about creative projects. She wrote Wikipedia articles for money. She was a child wrangler for a performance artist who sang covers of Michael Jackson songs with a choir of kids singing behind him. She answered an ad from a start-up online dating service called Tawkify that uses human matchmakers instead of computer algorithms to pair couples. Cooper has now been a professional matchmaker for almost a year.
“It was very, very exciting to me,” she says, noting that she learned quite a bit about what makes relationships work. “On this basic level, all humans basically want the same thing. There is this basic human need to be seen and to be loved.”
It’s this job — and her time at Brown — that led Cooper to Playboy. One of her college classmates, Zak Stone, had become an editor at Playboy.com. The site was looking for an online sex and relationships columnist, and Stone thought of Cooper, whom he’d known at Brown. The two dined together with others in a house on campus that Stone described as a Hogwarts-style dorm. The group would spend evenings swapping stories about daily trials and tribulations. Cooper was a good listener.
“She’s definitely always been someone who’s had interesting stories about sex and love — just a great person to talk to about this stuff,” Stone says. “I think she’s really empathetic — super kind and open to understanding.”
Stone was already using Cooper as a writer for the site and then pitched her for the columnist job. She seemed to him a great candidate because, besides her personal qualifications and her experiences at Tawkify, the company was trying to change the website’s focus to include more smart content and female voices — a nod to the glory days of the magazine when readers could plausibly joke that they were buying it for the articles.
Cooper says she has not met with much disapproval when she identifies herself as a Playboy columnist, especially when she’s speaking to older people who know the magazine’s literary history with authors such as Margaret Atwood, Norman Mailer, and Truman Capote.
Eaton says she’s pleased that Cooper is part of the brand’s commitment to that kind of writing. “I think that Playboy’s reinvention of itself is great,” she says, adding of her daughter, “I think her writing is very strong.”
Eaton also describes Cooper as someone who gives smart advice but is also open to receiving it. “That’s who she is — wise and level-headed.”
She admits that her daughter’s job may raise eyebrows in some circles, but she’s confident that Katherine is comfortable with it. Eaton said it probably helped that Cooper grew up in a somewhat atypical family where her mother was the breadwinner, and Eaton’s own mother wasn’t married until 38.
Cooper’s father is just as supportive.
“First off, I’m just glad she has a job,” Paul Cooper says, with a laugh.
He says he’s decided not to read the column because it might be weird as her dad, but he thinks the column is right for her. “Advice is advice,” he says, adding that Katherine’s background in theater has turned her into someone who is intuitive about people. “In the theater arts you’re interested in the underlying emotions of the character.”
The matchmaking has also helped with the Playboy job. Cooper says she’s learned how people behave when they’re lonely. She sees them at their best and worst. She sees how they limit themselves.
“People are funny. The more people have extensive checklists about what they want in a partner, the less happy they are.”
As for whether she’ll be a matchmaking, sex guru forever, Cooper guesses not. “I’m an artist and a writer before I’m a matchmaker.”
Meredith Goldstein, Globe reporter and “Love Letters’’ columnist, can be reached at email@example.com.