Every time Geraldine Hickey goes for a run outside, a habit established three years ago at the end of lockdown, she puts on a yellow legionnaire hat with the words “Perhaps To Drugs” on the front.

“I can’t wear caps,” says the 45-year-old comedian. “My head’s too small. My ears are too high.”

Hickey, sitting in her flat in Collingwood, grabs a cap from a cupboard behind.

“I just have to show you how bad I look in a cap.”

She pulls it on, the sides completely covering her ears.

“See?” she says. “It looks like I’m going through chemo.”

She swaps it for the legionnaire hat.

“It was Dr Karl Kruszelnicki,” she says. “That’s where I saw it. He was wearing one in a TikTok years ago, and my wife found them online and bought two, so we’ve got matching legionnaires, and I really like it.”

Running is a big part of Hickey’s life, helping with her health and, broadly, her motivation. It has spilled onto Instagram via regular “Running Update” videos, usually featuring the yellow legionnaire hat.

She stops running to chat beside cows or train tracks in rural Victoria, city rivers in Adelaide, coastal waters in Cairns, canals, meadows, and Arthur’s Seat, an ancient volcanic hill in Edinburgh.

Her video cameos, filmed on her propped-up mobile, are check-ins, steps in a journey to finish ambitions or plans.

“In everyday life, I think I struggle with completing tasks,” she says. “Because, like every other adult in the creative industry and everywhere else, I got diagnosed with ADHD.”

This knowledge has changed everything.

“People diagnosed with ADHD talk about grieving the life they could have had,” she says. “I had a whole year between a probable and confirmed diagnosis to think about it, and I was able to go: ‘Oh, yeah, that’s why I didn’t do well at school.’

“That was the biggest thing. It was just a relief to know that I wasn’t dumb and lazy. I also think it is quite incredible the stuff people accomplish when they are undiagnosed, what they’ve achieved in their life. It’s just amazing.”

Hickey is four days out from having a wisdom tooth extracted. When it arose 20 years ago, she couldn’t afford the procedure, and she was fresh from being named runner-up at Raw Comedy at the 2001 Melbourne International Comedy Festival.

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She’s still not over a tooth removal in 2021, one week after winning Most Outstanding Show at the Melbourne International Comedy Festival for What A Surprise, her 13th solo show, in a career that also includes appearances on countless TV panel shows, roles on Fisk, Rosehaven, Get Krack!n, Metro Sexual, along with her comedy special What A Surprise and five years as a much-loved Triple R Breakfasters presenter (featuring her wife, Cath Bateman, proposing to her live on-air).

“After the festival I was all high on life, everything’s great and then my tooth and pain,” she says. “I thought: ‘Better go to a dentist.’ I am very anxious about the dentist, but I reasoned: ‘It’s probably infected, I’ll have to have antibiotics, wait for that to go down and then have it out.’

“But the dentist said: ‘We’ve got to pull that out now.’ And I said: ‘No, no, wait.’ And the dentist said: ‘No. It has to be now.’ And I said: ‘Is there gas?’ And they said: ‘No.’ Valium was possible, but it would take too long, and this was urgent.

“I had a local anaesthetic, but … it was so traumatic.”

The thing about this story is that while Hickey was deeply affected by the event, when she tells it, it’s funny.

Her comedy is deftly honed and crafted, but it’s also innate and real. As MICF director Susan Provan said of Hickey’s 2021 win, “She manages to explore universal themes in such a modest and easy-going manner with totally relatable and seemingly uncomplicated anecdotes.”

Audiences are as transfixed as they are enveloped in relatability when Hickey describes being unable to find the car at IKEA, not making it to the end of a zip-line, trying to free a boat from a trailer; attempting to dig up wads of agapanthus (to create a famous “lesbian pit”), and loving bird shows so much she designs calendars and stubby holders adorned with her favourite birds each year to sell.

The stories are beautifully structured, often slow-burning wonders, but they are indefinably and genuinely her.

In Hickey’s new show, Don’t Tease Me About My Gloves, she opens another window into her state of mind.

It is partly about discovering she has Raynaud’s phenomenon, an incurable but manageable condition involving the short-term interruption of blood flow to the extremities, such as fingers and toes.

“It’s affected my life dramatically,” she says. “I was just like, ‘How have I never heard of this thing?’ It’s so frustrating and annoying because if it’s cold, all of a sudden, I can’t use my hands.”

By discussing the gloves in a live comedy show, she hopes to reduce the need to explain them and hear from audience members about their frustrating health conditions.

“I’ve been getting responses from people saying it’s so nice to be validated for these, I guess, minor medical conditions,” she says. “All I’m doing is saying, ‘Oh man, that’s f---ed’.

“In the bigger picture, though, I think society as a whole now is frustrated. Just, ‘f---ing hell, what do we have to do? Why is everything so bad again?’ I want the audience to know it’s OK to be angry and frustrated about something, whether it’s something small in your life or the bigger world problems.”

Hickey’s past shows have explored the positives in her life, beginning with Things Are Going Well in 2019 and, most recently, Of Course We Have Horses, which she toured at the 2023 Edinburgh Fringe.

“I was like: ‘Oh, everything’s good, so how do I make that funny?’ But the last year hasn’t been good. There’s just a bit more emotion. It’s not just, ‘oh, I did this, and this is really nice’. Now it’s like, ‘arrrgh!’”

Last year, during the Melbourne comedy festival, Hickey’s father died, and in November, her good friend and fellow comedian Cal Wilson passed away from a rare form of cancer.

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“It’s weird,” she says. “In the new show, I don’t mention Cal at all. When I started writing it, it was always going to be about grief, but not …”

Hickey starts to cry, and I apologise.

“Don’t worry,” she says. “It’s all good. Like, I really like it. So thank you, actually. So, I started with Dad. And I had to give up drinking because of this medication that I’m taking for arthritis. Because Dad had dementia, it’s a long goodbye so, it’s a relief when they die. You don’t have to deal with the shock.

“I found myself when Dad died, going, ‘man, I’m nailing grieving’. I’m doing all the right things. I kind of felt really good. I was absolutely prepared, I’d already written the eulogy. Then, when I had to give up drinking, I realised I was having all these proper grief emotions. I was angry and frustrated about giving up drinking. I started writing the show, and then Cal passed away.”

Hickey says she knew Wilson was in hospital from the day she was admitted.

“We thought she was gonna get better,” she says. “There was a lot of unknown. It was scary. But I always clung on to this hope. We all thought the doctors were going to figure out what it was, and then they’d fix it, and then she’d get better.

“To be honest, I spent a lot of time watching House, the TV show. Because, every episode, someone would come in with a medical mystery, and they’d be on death’s doorstep, and then they’d figure out what it was and then get a pill and it would all be resolved.

“And I was thinking, ‘Dr House is gonna get in there and figure it out.’ And it didn’t happen.”

Hickey says it is too soon to talk about her grief for Wilson in a live show.

“It’s so funny because it was Cal who said, ‘when you’re talking about tragedy in comedy, people are happy to see scars, not wounds’. People know that I’m grieving for Cal, but I don’t need to say that out loud [in a show].

“I feel really lucky that I was a very good friend of Cal’s. She had such an influence on so many people’s lives. I’m guilty of feeling that I don’t have the right to talk about my grief for Cal when there’s people that are grieving more, people who were closer to Cal.

“But, I see other people doing it and I’m ‘No, you’re allowed to grieve. Your grief is valid.’ There’s this outpouring of emotion from people that might have only met Cal once. And I think all those feelings are valid.”

Don’t Tease Me About My Gloves is about Raynaud’s phenomenon, arthritis, giving up alcohol, and her father dying.

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“And climbing Arthur’s Seat in Edinburgh,” she says. “It’s so weird. Everyone says, ‘you gotta do that’ and every morning I did and it shrouded in fog and you’re four steps from a precipice. Like, it’s terrifying.”

“The show’s just about what I’ve been up to in the last year,” she says. “People just want to know what I’ve been up to, the details of bits and pieces.”

She says she may yell and swear more than in previous shows.

“I’d like to think it’s justified swearing,” she says. “I don’t know what justified is but it’s mostly just the f-word as I try to convey an emotion. Which might be the anger.

“It’s just, well, f---.”

Geraldine Hickey performs Don’t Tease Me About My Gloves at the Melbourne International Comedy Festival from March 28 to April 21; and at the Sydney Comedy Festival on May 10-11.

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