Unlikely media couple Caleb Bond and Rosie Waterland have split just months after a scandalous interview in which they admitted spending “five days together in a hotel room” after their first meeting.
Waterland, a feminist writer and comedian, was 30 when she first came into contact with Bond, then an outspoken conservative 17, in 2016. When he was a little older, in 2019, the couple met in Adelaide and their relationship flourished.
The couple gave a highly commented interview in good weekend magazine last July, in which Bond, now a Sky News Australia presenter, said he had “a thing for older women” and the first thought he had when he met Waterland was “you’re hot”.
At the time, Bond was 20 and Waterland was 33, and “we met in a hotel room and didn’t go out for five days.” We just clicked.’
“At the end of the week, we were a couple,” he said.
But Daily Mail Australia has confirmed that Bond and Waterland have split; Waterland will debut 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’, with permission
Waterland and Bond split after giving a scandalous interview about their 13-year age difference, sex life and disparate 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 told Good Weekend that their political differences fueled their banter and fostered a shared empathy, saying she would “make fun of him for his pro-monarchy stance” and “we grew this unlikely friendship online.”
When Waterland, now 37, visited Adelaide from Sydney in 2019 and Caleb agreed to meet to “see if the chemistry translated from writing to speaking”, they got a hotel room.
“By then he was 20 years old and the skinny teenager in his photo had disappeared,” he told GW.
“He had grown his beard, it had filled out and had a shine to it. The jokes translated and we’ve been a couple ever since.
‘We are a strange couple. He wears a shirt, cufflinks, tie, suit and tweed jacket with a pocket square. I wear t-shirts. Caleb doesn’t have one; 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 the word has been co-opted by extremists. We have furious, yet respectful, discussions.
In the interview, Waterland spoke of her difficult childhood “of abuse and neglect.”
‘My parents were alcoholics and I lived in more than 100 houses, including foster homes.
‘My PTSD is largely under control, but last year I was hospitalized three times. We started fighting a lot. She said: “I feel like I’m dating a different person. The Rosie I knew is gone.”
Waterland said that if she was provoked, Bond would calm her down.
Bond said in the interview, which was published shortly before their split, that he liked older women and immediately thought “she’s hot” before spending the week in bed together.
For his part, Bond 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 that “they were both stubborn” but that “clashing can make them better people.”
“I don’t like being told I’m wrong, which Rosie sometimes does, like any good girlfriend,” he added.
‘It’s surprising how often we find ourselves at the same stage, even though the path we take may differ. I’m not sure who’s more annoying: her or me.
Waterland and Bond are understood to have split “about six months ago”, shortly after the article was published, but remain on good terms.
“It was an amicable breakup,” a source said.
On Thursday, Waterland posted a photo on Instagram of her kissing James Joseph Asciak, her new boyfriend, while they sat in the back of a camper.
The couple met when Asciak drew a drawing of Waterland as Polly Pocket, the small dolls marketed by Barbie maker Mattel, which became a fad in the 1980s.
Waterland and her new boyfriend James Asciak take 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 in love with a guy who draws you like Polly Pocket and very conveniently owns a caravan.”
He said this was “just when you’d like to escape on a road trip to try every local bakery between Sydney and Melbourne”.
‘Stay tuned for all the tart/lamington/vanilla slice reviews. We are currently accepting bakery recommendations, please and thank you.’
Pictured is Waterland’s new man, James Asciak.
On his Instagram page @jajo.in.a.van, Asciak said he moved from his home to his motorhome a year ago “and embarked on an open-ended adventure traveling around Australia.”
‘It has been a life-changing experience to discover who I am outside of my work, to like myself a little more and to explore the unknown and unexpected.
“Nothing more unexpected than attracting @rosiewaterland to her Polly Pocket house, and that spark being the start of a great relationship and making me want to rejoin the real world.
‘We’re currently wandering from Sydney to Melbourne (eating vanilla slices and cakes) and can’t wait to visit you all soon!
“So yeah, I guess the moral of the story is that if you like a person, draw a picture of them and everything will turn out great… and you’ll have someone to share the next adventure with.”