Mr. Lerer (Photo: Lerer Ventures)

JackThreads, the members-only shopping site for sartorially savvy fellows, launched a new feature last week that may appeal to those whose shopping habits are calibrated to 1960s-era PanAm flight. The new customer service tool is called "Jill Says," and it allows members to live chat with an all-female team of customer service representatives and stylists called "The Jills."

Skeptical that the company would really hire a staff of women to coddle its shoppers in the safe space of a chat box, we ran a quick Turing Test.

"Hello, my name is Jill. I'm your personal stylist today! What can I help you with?"

"Hi! Are you a real person? Or an automated service," we asked.

"lol I'm real," she responded. We were already feeling the love.

The Jills are trained like any other JackThreads customer service team, Ben Lerer, Thrillist's CEO, told us by email, and work out of the company's Columbus, Ohio office.

"'The Jills' is a combo of the Jack parallelism and the simplicity of the name," said Mr. Lerer. "Our customers have always asked us if we’d ever launch JillThreads for women’s clothing -- so this name seemed to already resonate strongly with them." Despite the fact that many JackThreads customers frequently ask for customer reps by name, The Jills won't be using their real ones--at least not for now, said Mr. Lerer.

Luckily for those growing bored with the Second Life dating scene, The Jills will be available from 9 a.m. to 9 p.m. to assist users with style questions--oh, and also to flirt.

Mike Novotny, the general manager of JackThreads, told the Wall Street Journal: “Our guys are younger, and if they want to flirt it’s easier to do over chat. They don’t have to pick up the phone, and this gives the freedom to have a little more fun.”

Surely there are a few gay men browsing the online racks of JackThreads. Why no flirty stylists for them?

"It’s our belief that gay men would love shopping advice from knowledgeable women who are into fashion and style just as much as our straight customers," Mr. Lerer told us. We suppose gay men can get the tips without the flirting.

The Journal also pointed out that one JackThreads member has already been banned due to his inappropriate contact with The Jills. "He pushed the limits beyond flirtation to a place that made our employee uncomfortable and that’s where we draw the line," Mr. Lerer clarified. Hey guys, no asking the Jills what they're wearing.

Ask Jill should appeal to the same subset of dudes who are looking for love on Airtime. Hey, it's more discreet than a trip to Hooters, and cheaper than a call to 1-800-US-GIRLS.

Ah, modern love.

The New York Times

Founder Ben Lerer is non-plussed. “That’s a very old media way of thinking about things,” Lerer, 29, co-founder and chief executive of Thrillist, told the NYT. “This is not a digital magazine that sells some stuff. This is the beginning of what a new media company looks like.”

The most interesting data point, buried way down at the bottom, is that Lerer expects Jack Threads, a members only shopping club that Thrillist acquired back in May of 2010, to bring in $20 million in revenue this year. That's double its ad business from last year and half of the $40 million in revenue Lerer says he expects Thrillist to clock in 2011.

“We had an audience who trusted us and lots of evidence people did what we suggested,” Mr. Lerer told the NYT. “Why are we sending all the value to the people we write about editorially? Why can’t we capture some of that value ourselves?” We're sure the Grey Lady couldn't agree more, although her plan is put new walls up, not tear old ones down.