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The Return of TV's Unlikeliest Heroine: Abby McEnany's Depressed Dyke

Abby McEnany

The Showtime series about the trials and triumphs of a middle-aged Chicago lesbian returns for a second season filled with humor and heart.

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As the second season of Work in Progress opens, protagonist Abby has found that life has gotten in the way of her plan to end hers. She's still seeking the perfect therapist, has let best friend Campbell move in with her, and is trying to atone for having shouted the deadname of the transgender man she was recently dating.

And it's all pretty damn funny.

It's not funny at the expense of people with mental health issues or of LGBTQ+ people, but self-described "masculine queer dyke" Abby McEnany and her co-creator, Tim Mason, find ways to make the characters' everyday struggles and triumphs funny, touching, and totally relatable.

"It's a very real telling of a life that is messy," says McEnany, who notes that the character of Abby is based on herself, but loosely so.

[You can listen to Abby McEnany on the LGBTQ&A podcast here.]

McEnany and Mason have long been mainstays of the Chicago improv scene, and after she did a one-woman show called Work in Progress, Mason suggested they turn it into a TV series. Showtime picked it up, and the first season was a hit with both viewers and critics. Season 2 opens Sunday.

The series is set and filmed in Chicago, showcasing the vibrancy and diversity of the city and its LGBTQ+ population. "The queering of the world on-screen was really important" in writing and casting decisions, McEnany says.

Abby and King

Abby and her friend King (Armand Fields) have a chat

"It was very important from the get-go that we do our due diligence," she explains. "If we have a trans character, they will certainly be played by a trans actor. ... There's so much talent here that hasn't been given an opportunity." Chris, the trans man who broke up with Abby at the end of season 1, is played by nonbinary actor Theo Germaine (The Politician). There's plenty of out talent behind the scenes as well; for instance, the show's writing staff includes esteemed trans filmmaker Lilly Wachowski, in addition to McEnany, Mason, and others.

McEnany herself is representing an underrepresented population. "I'm not a Hollywood queer," she observes. "I'm just this old masculine queer dyke with gray hair."

The series makes points about representation and other LGBTQ+ issues without being didactic. "We always want to make sure that we are not doing a TED talk," she says. "We want to show but not tell."

It shows, among other things, the difficulties that masculine-appearing women like Abby face when using a women's restroom, and it details Abby's efforts to have actress-comedian Julia Sweeney retire the character of Pat, as the whole point of the character is that you couldn't tell if Pat was a man or a woman. Sweeney hilariously plays a version of herself; that version remains clueless about how offensive the character has become to trans, nonbinary, and gender-nonconforming people.

In the Abby-Chris storyline, it makes clear that deadnaming is one of the worst things you can do to a trans person but makes us empathize with Abby as she berates herself for doing it in a moment of rage. In other plotlines from the second season, we learn more about Abby's quirky coworkers, her childhood, and her continuing therapist quest (she rejects one because he misstates a common expression).

Abby and Campbell

Abby parties with her best friend, Campbell (Celeste Pechous, left)

And the interactions between Abby and Campbell (Celeste Pechous) are an authentic depiction of friendship. Campbell's dog has recently died, so she's moved in with Abby until her period of grieving is over. They stick together through the good times and bad. The show finds much humor in scenes where they go on a bus tour of Chicago's 1920s-era gangland sites; they're skeptical because it's such a tourist thing to do, but they have to go because it's a birthday celebration for Campbell's grandmother. The passengers end up having fun spotting locations for The Good Wife and The Good Fight, and offering support to their gay guide, whose ex-partner is working for a rival tour company.

McEnany won't speculate if there will be a third season of Work in Progress. "I can't even believe we got this far," she says. She feels fortunate. "I actually got a job," she says. "I get to work with Lilly Wachowski. She came out of retirement. ... I get to work in Chicago, to be able to bring work here and give opportunities."

"I still can't believe this is part of my life," she adds.

Season 2 of Work in Progress opens Sunday at 11 p.m. Eastern/Pacific on Showtime. Find out more here and watch a trailer below.

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Trudy Ring

Trudy Ring is The Advocate’s senior politics editor and copy chief. She has been a reporter and editor for daily newspapers and LGBTQ+ weeklies/monthlies, trade magazines, and reference books. She is a political junkie who thinks even the wonkiest details are fascinating, and she always loves to see political candidates who are groundbreaking in some way. She enjoys writing about other topics as well, including religion (she’s interested in what people believe and why), literature, theater, and film. Trudy is a proud “old movie weirdo” and loves the Hollywood films of the 1930s and ’40s above all others. Other interests include classic rock music (Bruce Springsteen rules!) and history. Oh, and she was a Jeopardy! contestant back in 1998 and won two games. Not up there with Amy Schneider, but Trudy still takes pride in this achievement.
Trudy Ring is The Advocate’s senior politics editor and copy chief. She has been a reporter and editor for daily newspapers and LGBTQ+ weeklies/monthlies, trade magazines, and reference books. She is a political junkie who thinks even the wonkiest details are fascinating, and she always loves to see political candidates who are groundbreaking in some way. She enjoys writing about other topics as well, including religion (she’s interested in what people believe and why), literature, theater, and film. Trudy is a proud “old movie weirdo” and loves the Hollywood films of the 1930s and ’40s above all others. Other interests include classic rock music (Bruce Springsteen rules!) and history. Oh, and she was a Jeopardy! contestant back in 1998 and won two games. Not up there with Amy Schneider, but Trudy still takes pride in this achievement.