‘Work in Progress’: The hilarious hardship of being smart, funny and queer in Chicago

“I haven’t been out for a drink with an attractive woman in a really long time.”

“Actually, I’m a trans man.”

“Well I haven’t been out with an attractive trans man in ever…” – Conversation between the lead character and a prospective romantic partner in “Work in Progress.”

In the series premiere of the whip-smart and provocative and hilarious new Showtime comedy “Work in Progress,” 45-year-old Abby is on a first date in a Chicago restaurant when she spots author-actress-comedian Julia Sweeney (as Julia Sweeney) at the bar.

“I think that’s Julia Sweeney from ‘Saturday Night Live,’ ” Abby explains to her much younger date, who has never heard of the great Julia Sweeney.

“She played [the androgynous character] ‘Pat’. … That woman over there ruined my life. That was the only joke of the whole premise, ‘Is that a man or a woman?’ And for years after that, people would say I looked like Pat.”

A confrontation ensues — but I’ll give away no more than that, other than to say it’s handled with intelligence and grace and humor, and it launches a myriad of funny, authentic and instantly involving storylines in what should be one of the breakout new TV series of 2019-2020.

Set and shot in Chicago and premiering at 10 p.m. Sunday on Showtime, “Work in Progress” is the brainchild of local improv stalwarts Tim Mason and Abby McEnany (who stars as the actual work in progress) and features a major marquee name as co-executive producer and co-writer: the locally headquartered filmmaker Lilly Wachowski of “Matrix” and “Sense8” fame. (Full disclosure: My sister was the show’s property master.)

I’ve seen the first four episodes of “Work in Progress,” and suffice to say we’re off to a roaring start.

This is a dark and frank and wickedly funny profile of a likable, lightning-quick, middle-aged queer woman who can own a room when she’s feeling confident but is still struggling to make her mark on the world and is prone to deep depression.

Episode One is titled “180 Almonds” because Abby has laid out 180, well, almonds, and will throw out one per day as a morbid countdown to suicide.

“I’m going to kill myself in 180 days if things don’t get better,” says Abby. “I’m 45, I’m fat, I’m this queer dyke who has done s--- in her life and THAT is my identity?”

Spoiler alert: We’re rooting against the almonds, because that would pretty much end “Work in Progress” when it’s still a most promising work in progress.

McEnany has that intangible but immediately recognizable star quality, not unlike when we first saw Ellen DeGeneres or Roseanne killing it in comedic alter ego roles.

Of course, these are different times, and Showtime ain’t ABC.

Thanks in no small part to the pioneering strides made by Ellen and others that followed, Abby is here and queer and wonderfully so from the get-go.

Not that some of Abby’s issues and misadventures are all that different from the dilemmas faced by all manner of comedic leads through the decades. She has a feisty but loving grown-sibling dynamic with her suburban-based sister Alison (Karin Anglin), and she’s just starting to date someone who’s half her age — which can make for some ridiculous, laugh-out-loud scenarios.

Abby is in the throes of a deep funk. Her therapist has just died. She’s stuck in a nowhere daytime job as a temp. When she rejoins a weight-loss program and steps on the scales, she learns she’s gained 17 pounds. since her last visit.

“I’m surrounded by people who are like full selves, and I’m like this building that’s been delayed,” says Abby, as we cut to a shot of one of the many, many downtown Chicago buildings in progress.

“Work in Progress” is filled with such strong writing and nifty visual references, as Abby navigates that precarious tightrope between comedy and tragedy.

Downstate Illinois native Theo Germaine is having quite the breakthrough year (and deservedly so), first with a prominent role in the Netflix series “The Politician” and here as the romantic interest Chris.

Even though Abby is acutely aware of the vast chronological and lifestyle chasm between them (as evidenced when Chris takes Abby to a “Queer Wonderland” nightclub experience and Abby tells Chris she looks like “Mitt Romney Junior” compared to all the sexually expressive millennials doing their thing), the budding romance just might blossom.

Chris seems sincere and appears to be genuinely interested in Abby.

If not, we’re going to despise Chris, because by that point we’re already deeply committed to Team Abby.