Things to Do

There’s a New DC Company That Will Plan Bespoke Weekend Outings and Downtime for You

Ask Jenna is a very 2021-style concierge.

An Ask Jenna member and his family on a horseback-riding experience. Photo courtesy of Ask Jenna.

If you were to ask her, Jenna wouldn’t call herself an event planner or a concierge. She’s just the person who is always out, the face of a new DC service—Ask Jenna—that will plan and personalize your days and nights out.

For $129 a month, Ask Jenna arranges outings including sports games, concerts, outdoor recreation, Michelin-starred dining, and other activities for its members. Customers can pick from a variety of options based on preferences they list in their membership profiles and a half-hour call with an “experience architect.” They also get Jenna’s Notes—a guide on how to optimize their experience.

It’s a lot of work for a woman who isn’t even real.

“Jenna” is actually the concoction of Janece Kleban and Jenny Shtipelman, a combination of their names and the avatar behind their service. The duo went from good friends to business partners. “You ask Jenna, and she will take care of it for you,” Shtipelman says.

The idea came to Kleban, a DC native, after she organized an outing with her husband. “I ended up marrying a guy who can not plan anything,” Kleban says, “Anything.” He suggested she turn her ability to put together fun days out into a full-time job. 

She left her role as Chief Development Officer at the Goodwill of Greater Washington, reached out to Shtipelman, senior vice president at National Capital Bank of Washington, and the two opened the service to members in 2019. 

An Ask Jenna member and his son on a virtual-reality experience. Photo courtesy of Ask Jenna.

Months later, Ask Jenna found itself in a pandemic-battered city with many residents hesitant to go out like they used to. Kleban says the different comfort levels of residents forced them to think creatively, and pivot to more outdoor and virtual experiences. Today, Kleban and Shtipelman plan outings for about 50 members and their guests. “Our sweet spot are folks in their mid-30s to mid-to-late 50s,” Kleban says, “people who are entrepreneurs, people who are executives or in high leadership positions.”

Kleban says the company will bring on full-time staff in 2022 as they roll out a texting platform to keep members up-to-date on their experiences. Eventually, they hope to expand the concept to other cities.

“The goal right now is to really optimize how we’re using this technology, and optimize the business connections that [Shtipelman] is bringing in,” Kleban says.

Zach Bright

Zach joined Washingtonian in October 2021. In the past, he’s written for The Colorado Sun, The Nevada Independent and SRQ Magazine.