Louis Tomlinson arrived by speedboat. His fans arrived by seaplane. And for one hour on a secret stretch of Sydney Harbour, 20 of them got the closest thing to a private audience with a pop star that a radio station can engineer.

The KIIS Presents iHeartLIVE event, hosted by Kent “Smallzy” Small, celebrated the Australian leg of Tomlinson’s “How Did We Get Here?” World Tour. ARN chose the 20 superfans from more than 15,000 entries lodged in a single week, as Mumbrella reported, then flew them across the water with Sydney Seaplanes to a Rose Bay lounge stocked with custom “Imposter” mocktails.

Tomlinson, who took the boat, was unbothered by the ride. “That was fun, actually, to be fair,” he said, while Smallzy confessed he had come close to asking the captain to ease off.

The former One Direction singer has history on that harbour. He first visited Australia at 20 or 21, and the first thing the band did was get out on the water. “Especially at that time in One Direction, everything was so new to us,” he said.

Downtime, though, is still rare. “Not enough, to be honest, especially on these kind of tour legs,” he said. A mate who lives in Sydney has given him a reason to stay a little longer.

Asked by fan Gemma about the career moment that stuck with him most, Tomlinson went back to the first time he played The O2 in London on his second tour. “Normally those big shows get the better of me,” he said. “That was like I unlocked something that day.”

He called it “proof of concept that day that I could do it at that level,” and said the big rooms have felt less intimidating ever since.

Melbourne fan Hannah asked for his favorite lyric he has ever written. He picked a line from “Saturdays,” off 2022’s Faith in the Future: “No matter how much you want it, some things change.”

“It’s not like a clever metaphor and it doesn’t even sound that great written down, but every single time I sing it, there’s just something really, really poignant about that,” he said. He added that the emotion of the song only fully landed once he started performing it live.

Jackie, 22, from Sydney, asked what he would tell his younger self. “I’m quite hard on myself. I have quite high expectations for myself and for this project,” he said. “If I had my time again, I’d probably just take the pressure off myself a little bit and say it’s all going to work out.”

Bella, who had just turned 18, asked which of his songs is the most self-reflective. “Behind closed curtains, I’m quite a deep guy, to be honest,” he said, before landing on his 2019 single “Two of Us.”

On his third album, How Did I Get Here?, released January 23 and his second UK No. 1 album, Tomlinson was typically quick to redirect the credit. “I worked really hard on that record, so it’s a really good feeling for me, but also it’s a testament to the fanbase,” he said. “It just shows our staying power as a collective, me and the fans.”

Then came the dream collaboration question from fan Leah, and Tomlinson did not hesitate. He wants to make something with Sydney band DMA’S. “I’ve known the boys for a bit,” he said. “All really cool lads. So yeah, I think that’d be really cool.”

The hour closed with the debut of a new game, “iHeart or iHate,” with Tomlinson holding a paddle and ruling on modern life.

Reclining your seat on a short flight? He sat on the fence. “I personally, if it’s a short flight, I probably wouldn’t. But I do think anyone who whinges about it is probably a bit grumpy.”

Taking calls on loudspeaker? A clean hate. He and Smallzy agreed the offender is usually a businessman in an airport lounge “basically trying to show that he’s more powerful.”

Watching fan edits of himself? Also on the fence, and he insists his For You page is not wall to wall Louis. He does have a grievance about photos, though. “They often do pick a botched photo of me,” he said. “I think they do it on purpose.”

The one he could not fence sit on was voice notes. “I really hate it,” he said. “Either ring me or we’ll meet up and have a beer and chat about it.” His real pet peeve is the long ramble played back at 1.5 speed, in which case he reckons you should either say less or just call.

The Australian run wrapped at Riverstage in Brisbane on Saturday, October 24, after shows at John Cain Arena in Melbourne and The Hordern Pavilion in Sydney, with Rum Jungle on support, per promoter Untitled Group. South America is next on the schedule in 2027.

Tomlinson told Rolling Stone Australia earlier this month that he spent years unsure whether he could tour at this level at all. On a boat in the middle of Sydney Harbour, surrounded by people who flew in on a seaplane to ask him questions, the answer looked settled.

Hear the full conversation on The Smallzy Show, weekdays on KIIS in Australia and on demand on the iHeart app globally, in Early Drive from 3 to 4 p.m. and at Night from 7 to 9 p.m.

102.5 The Lake