Conservative Sky News host Caleb Bond, 24, SPLITS from feminist columnist Rosie Waterland, 37, after their unlikely love story baffled colleagues… and she already has a new man

Unlikely media couple Caleb Bond and Rosie Waterland have split just weeks after giving an outrageous interview in which they admitted they spent ‘five days in a hotel room’ together after first meeting.

Waterland, a feminist writer and comedian, was 30 when she first connected with Bond, then an outspoken 17-year-old conservative, in 2016. When he was a little older, in 2019, the two in Meet Adelaide and their relationship. bloomed

The two sat down for a much talked about interview with Good Weekend magazine last July, in which Bond, now a Sky News Australia presenter, said he had ‘a thing for older women’ and his first thought when he met Waterland was ‘you’re hot’.

Bond was 20 at the time and Waterland 33, and ‘we found ourselves in a hotel room and didn’t leave for five days. We just clicked.’

“By the end of the week we were a couple,” he said.

But USA Online Post Australia confirmed that Bond and Waterland called it quits not long after their Good Weekend feature hit the papers – with Waterland debuting her new boyfriend James Joseph Asciak this week.

Left-wing feminist Rosie Waterland was 30 when she met conservative commentator Caleb Bond when he was just 17.  They have now gone their separate ways.  Above, posing for a Good Weekend column about couples, 'The Two of Us', provided with permission

Left-wing feminist Rosie Waterland was 30 when she met conservative commentator Caleb Bond when he was just 17. They have now gone their separate ways. Above, posing for a Good Weekend column about couples, ‘The Two of Us’, provided with permission

Waterland and Bond split after they gave an outrageous interview about their 13-year age gap, their sex lives and differing political views

Waterland and Bond split after they gave an outrageous interview about their 13-year age gap, their sex lives and differing political views

Waterland met Bond online when he was just 17 and three years later they 'stayed in a hotel room for five days and didn't leave' before embarking on a romance that has now ended

Waterland met Bond online when he was just 17 and three years later they ‘stayed in a hotel room for five days and didn’t leave’ before embarking on a romance that has now ended

Waterland told Good Weekend their political differences fueled their banter and sparked a shared empathy, saying she would ‘tease him for his pro-monarchy stance’ and ‘we’ve cultivated this unlikely online friendship’.

When Waterland, now 37, visited Adelaide from Sydney in 2019 and Caleb agreed to meet to see if the chemistry translated from typing to speaking, they found a room at a hotel.

“He was 20 at the time and the skinny teenager from his sideline photo was gone,” she told GW.

‘He grew a beard, filled out, had a glow. The banter was translated and we have been a couple ever since.

Waterland said they disagree on most things, including how to dress and politics

She chose to dress casually while Caleb (above) 'doesn't own a T-shirt'

Waterland said they disagree on most things, including how to dress and politics

‘We are an odd couple. He wears a shirt, cufflinks, tie, suit and tweed jacket with a pocket square. I wear T-shirts. Caleb owns none; he says they are unworthy.

‘I never thought I’d end up with a man who wouldn’t call himself a feminist.

‘He believes in equality but claims that the word has been co-opted by extremists. We have angry arguments, albeit respectful ones.’

In the interview, Waterland spoke about her difficult childhood ‘of abuse and neglect’.

‘My parents were alcoholics and I lived in over 100 homes, including foster homes.

‘My post-traumatic stress disorder is largely under control, but I was hospitalized three times last year. We started fighting a lot. He said: “I feel like I’m dating a different person. The Rosie I met is gone.”

Waterland said if she was activated, Bond would reassure her.

Bond said in the interview, which was published shortly before their split, that he was an older woman and thought immediately

Bond said in the interview, published shortly before their split, that he was an older woman and immediately thought “she’s hot” before spending the week in bed together.

Bond, for his part, told the publication that after the five-day session in the Adelaide hotel room, he drove to Sydney during the Covid pandemic and had ‘no choice but to move in with her’.

He said they were ‘both opinionated’, but that ‘headedness can make you better people’.

“I don’t like being told I’m wrong, which Rosie does sometimes, like any good friend,” he added.

‘It’s surprising how often we land in the same ballpark, even though the path we take may be different. Not sure who cares more: her or me.’

Waterland and Bond are understood to have split ‘about six months ago’ – shortly after the article was published – but they remain on good terms.

‘It was an amicable break-up,’ a source said.

On Thursday, Waterland posted a photo on Instagram of her kissing James Joseph Asciak – her new boyfriend – while they were sitting in the back of a camper van.

The couple met when Asciak drew a picture of Waterland as a Polly Pocket, the tiny dolls marketed by Barbie maker Mattel that became a craze in the 1980s.

Waterland and her new boyfriend James Asciak set off on a 'van life' road trip

Waterland and her new boyfriend James Asciak set off on a ‘van life’ road trip

Asciak, who previously ran a support group for children with disabilities called Wild Rumpus, and an occupational therapy rehabilitation service, Geronimo, is now embarking on a ‘van-life’ adventure with Waterland.

She captioned the photo: ‘Highly recommended: falling for a boy who draws a picture of you as Polly Pocket and very conveniently owns a camper van.’

She said it’s ‘right when you want to escape on a road trip to try out every local bakery between Sydney and Melbourne.

‘Stay tuned for all the tart/lamington/vanilla chip reviews. We are currently accepting bakery recommendations please and thank you.’

In the photo is Waterland's new man, James Asciak

In the photo is Waterland’s new man, James Asciak

Asciak said on his Instagram page @jajo.in.a.van that a year ago he moved out of his house and into his camper and set off on an indefinite adventure to travel around Australia.

‘It was a life-changing experience to find out who I am outside of my work, to like myself a little more and explore the unknown and unexpected.

‘None more unexpected than having @rosiewaterland move into her Polly Pocket house, and having that spark start a really good relationship, makes me want to rejoin the real world.

‘We’re currently winding our way from Sydney to Melbourne (eating our way through vanilla slices and pies) and would love to visit you all soon!

“So yeah, I guess the moral of the story is that if you like a person, draw them a picture, and it will all work out nicely…and give you someone to share the next adventure with. “