Dec 20, 2016 12:12 PM

Catholic rebellion, adulthood, and sexual trials are a few of the themes explored in the YouTube web series “Guilty” directed by Erin Conroy, a former East End resident.

In November, the second season of “Guilty” was selected for the 2016 NYC Web Fest held in Manhattan. Ms. Conroy recently moved from Chicago back to New York, just in time to attend the festival.

“I moved back at the beginning of November and the festival was the second weekend so it was like I moved back from Chicago and immediately had something fun to do with ‘Guilty,’ which was awesome,” she said.

Ms. Conroy described being selected for the film festival as a huge deal for her and her crew.

Originally from Aquebogue, Ms. Conroy attended Riverhead High School and in the summer traveled to Southampton for camp—her father, Paul Conroy, is the sales manager of The Press News Group, based in Southampton Village. After graduating from Siena College in Albany, Ms. Conroy finished her graduate degree at Long Island University in Greenvale. She moved to Manhattan, where she worked for NBC Universal, and she was eventually transferred to Chicago, where she graduated from The Second City Conservatory & Writing Programs and the iO Chicago Training Center, and where she met the “Guilty” cast and production crew—including the show’s stars, Katie Novotny and Emma Smith.

Ms. Conroy, Ms. Novotny and Ms. Smith wrote the second season together and are all credited as co-creators as well.

Ms. Conroy found that Chicago had a great community of actors that “Guilty” could tap into for a cast and crew.

“Chicago has a big improv and sketch comedy community, so we either met people in class or were on teams with them in shows and thought they were funny and asked them to be a part of it, and they agreed,” she said.

“Guilty” shows the lives of two mid-20s women living in the city of Chicago. Both grew up in strict Catholic families, sheltered from a normal adolescent life. The story follows the pair as they experience adulthood in a whole new light. Both seasons have 11 episodes, with episodes ranging from two to seven minutes long.

The show is based on a television pilot script that Ms. Novotny wrote for a class in Chicago.

“She grew up very Catholic, so she wanted to write about how you take those teachings that we were brought up with and how does that translate into our real lives as adults,” Ms. Conroy said. “It’s not a seamless transition by any means, so she thought it was funny.”

After writing the pilot, Ms. Novotny brought the story to Ms. Smith, who then helped craft the story even further. They expressed their desire to make the story into a web series and that’s when Ms. Conroy became involved. Ms. Novotny and Ms. Smith star as the two main characters while Ms. Conroy controls most of the production.

For the trio, working with a platform like YouTube for a web series came naturally to them.

“We were really the only ones at the time—among our friends anyway—that were really making stuff in Chicago. Now, it’s like all our friends are making web series and filming stuff and putting it out there and it’s more of a permanent art form then what we’re used to,” Ms. Conroy said.

At the NYC Web Fest this past November, the second season of “Guilty” was one of only two web series selected from Chicago.

“We were all so excited to have our work appreciated by an audience outside of our Chicago comedy community, especially because this season was such a joy to write and film,” Ms. Conroy said.

The achievement is a dream come true.

“Growing up on the East End of Long Island, having my work screened in New York was a full-circle moment,” she said. “I had always thought of New York as the ‘big time’ so I’m really proud of us and the work we’ve done.”

Writing for season three will begin in the New Year and the crew hopes to start filming in the spring. Throughout the writing process and pre-production, Ms. Conroy will work remotely from New York as she helps the crew in Chicago. Production might come to New York for a few episodes as well, she noted.

To watch “Guilty,” visit guiltythewebseries.com.