Bad dates, awkward hookups and the stories you’d only tell your closest friends are getting their moment on stage in Prospect Heights this week.

Awkward Sex… and the City, a long-running comedy and storytelling show hosted by local comedian and podcaster Natalie Wall, returns to Friends and Lovers in Prospect Heights on Sept. 25 — marking Wall’s first show since becoming a mom.

The show, which began in 2013, brings comedians together to share sex stories, dating and relationships through a mix of comedy and personal storytelling.

“We’ve been doing this Awkward Sex… and the City for a while now, and I’v never heard the same story twice,” Wall told Brooklyn Paper. “It’s a great space to talk about awkward sex, dating and other relationship stories.”

That variety, Wall said, is part of what keeps audiences coming back.

“A majority of us have had an awkward experience in that world; in dating, sex, all of that,” she said.

She added that one of her favorite parts is “to hear other people talk about it with such confidence and kind of knowledge on the other side.”

The concept was partly inspired by Wall’s longtime love of “Sex and the City,” though she said revisiting the iconic series as an adult made her notice some of the stories and perspectives that were missing.

Wall said that Awkward Sex… and the City has been ongoing since 2013, and has evolved with her life.Photo courtesy of Natalie Wall

“I was obsessed with ‘Sex in the City’ growing up,” Wall said. “But now that I’m older and rewatching, you just kind of see there’s so many gaps or so many things that have just kind of changed.”

Her show, she added, is intended to give people space to talk openly about those experiences — and hopefully realize that they are far from alone.

Wall has watched the show evolve alongside her own life. The series took a pause during the COVID-19 pandemic, but has continued to attract both longtime audience members and comedians who have returned over the years with new stories.

Now, Awkward Sex… and the City enters another chapter.

Wall recently became a mother, making the Sept. 25 performance her first since having her baby. Her last planned show was June 26 — her original due date — but her son arrived via C-section two days earlier than planned after he was found to be breech.

Motherhood has also given Wall a new perspective on the show’s central subject matter.

“It’s more of ‘how do I prep for the show now?’ more than how has the show changed,” she said.

She said she has also found herself thinking about how intimacy and relationships change as people get older and enter new stages of life.

“There’s definitely a whole new world post-kid,” Wall said. “For sure.”

That can mean thinking about everything from pregnancy and intimacy after having children to divorce, polyamory and the ways relationships change over time.

Wall said that Friday’s Awkward Sex… and the City show is her first back since becoming a mom.Photo by Damon Dahlen, courtesy of Natalie Wall

“What becomes awkward? What becomes weird, unsexy?” Wall said. “They show it with Miranda in ‘Sex and the City,’ but not much.”

For Wall, the humor is ultimately about more than getting a laugh.

“I think it’s just really great to have those outlets in place and knowing that it happens to everyone,” she said. “It’s not just a thing that only happens to you.”

The Sept. 25 lineup will feature comedians Micah Eames, Veronica Garza and Calvin Cato alongside Wall. Wall said audiences can expect a mix of perspectives and plenty of stories that may make them feel a little better about their own dating histories.

“I’ve got some of my favorite people on this show — good comedy friends, that are just so hilarious,” Wall said. “Audience members will experience a lot of different things from many of different perspectives, which I think is really cool.”

And if nothing else, Wall promises audiences of Awkward Sex… and the City will leave knowing they’re in good company.

“You’re going to feel so much better about yourself,” she said. “Because you’re gonna be like, ‘Wow. That’s never happened to me.’”

Awkward Sex… and the City begins at 8 p.m. on Sept. 25, with doors opening at 7:30 p.m. at Friends and Lovers, 641 Classon Ave. Tickets are $10 online and at the door.