Katherine Cooper said her mother has been nothing but supportive of her new role. “If a 66-year-old in Cambridge can do it, so can the world,” she said. Photo by Eileen Meny

As noted advice columnist E. Jean Carroll puts it, Katherine Cooper is “an unusual choice” for Playboy.

“She’s very Jane Austen,” Carroll explained. “It’s perfect.”

But it’s that same sense and sensibility that drew Cooper to the most Austen of places at Playboy (trust us, there is one): not to the full-page spreads in the middle of the magazine but to the “Sex & Culture” section on Playboy.com.

As the writer behind Playboy’s new advice column, “Just the Tips,” Cooper is part of an overall brand refresh that’s taking the 66-year-old magazine into the digital millenium, and beyond the expected issues-stashed-under-the-bed audience.

Cory Jones, one of Cooper’s editors at Playboy, describes the magazine’s recent explorations beyond nude celebrity photo shoots and scandalous John Mayer profiles as part of an “inclusive and progressive” digital culture set at Playboy.com.

Cooper isn’t the first female advice columnist to ever appear in Playboy, but her take on modern love, sex and dating is decidedly new territory for the notorious magazine. Beginning with the catchy title — a pun “that’s almost sweet,” as Jones said.

“About being a gentleman”

The magazine drew considerable attention in feminist circles for surprisingly “un-Playboy” content, shared widely around the web as examples of the magazine’s new look — including a rather hilarious (and refreshing) flowchart entitled “Should You Catcall Her?”

“It’s funny,” Jones said, “We didn’t initially see it as feminist … it’s more about human decency than anything. About being a gentleman.”

This part about “being a gentleman” is what most intrigues Cooper and her editors about her new role.

“We’ve gotten Playboy back to its roots,” Jones said.

Cooper comes to Playboy from Tawkify, a matchmaking service helmed by the legendary Carroll, voice of the longest-running magazine advice column in ELLE. There, Cooper flourished as a sharp matcher and devoted listener, calming even the most difficult of clients and leading seemingly-clashing couples to grand romance.

Beyond even that, Carroll says, Cooper has a “sixth sense” when it comes to relationships and dating.

“People are generally interested in trying to be good people,” Cooper said. “And they’re also trying to have sex. And those two things can be a lot to do at once.”

As Cooper explained in her initial column pitch to Zak Stone, “I said I wanted to address people’s real concern: love and sex are always confusing, they always will be confusing. That’s what makes them exciting.”

Cooper wants to address her column to both genders, answering questions that plague anyone in the Tinder age: “What’s a gentleman in this age? What’s a lady in this day and age?”

“An advice column rises and falls on the questions,” Carroll said. “Whenever I have a dull column, it’s because I had dull questions. And Katherine will never have dull questions.”

Cooper’s first column, published Sept. 17, is headlined by a decidedly un-dull question: “Can I pay my OKCupid date to have sex with me?”

Cooper’s advice-giving style is conversational but analytical, and not without the much-needed dose of cold reality.

“Will it be a Pretty Woman fantasy come true?” she writes to the OKCupid questioner. “Probably not.”

Advice on giving advice

Among her group of friends, Cooper is the go-to for a reality check, a moment of empathy or a word to the wise.

On a recent vacation in Montana, Cooper “fell off the grid” for some Internet-free relaxation — and when she returned to civilization, her iPhone was full of text messages from friends needing advice.

“I said to a friend, ‘Is this normal? That one would leave for three days and one’s entire friend group would freak out?’” she said.

She owes this sense of humorous whimsy to Carroll. Following the announcement of her gig at Playboy, Cooper called the ELLE guru for some immediate advice on giving advice.

“You just write engagingly,” Carroll said. “People read advice columns to say, ‘Thank God that’s not me.’ Or ‘Oh, God, that was me.’”
In addition to Carroll, Cooper looks to famed advice columnists such as Cheryl Strayed and Dorothy Parker — and of course, the friends and family who blew up her phone on that trip to the wilderness.

“Sometimes we misconstrue advice as having to give a moral judgment on something,” Cooper said. “But to truly not know the answer to a question immediately is a wonderful thing. You have to ask yourself.”