Unlikely media couple Caleb Bond and Rosie Waterland have split just months after a scandalous 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 hooked up with Bond, then an outspoken 17-year-old conservative, in 2016. When he was a little older, the pair met in Adelaide in 2019 and their relationship blossomed.
The pair gave a much-discussed interview 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’.
Bond was twenty at the time and Waterland was 33, and ‘we found ourselves in a hotel room and didn’t leave for five days. It just clicked.’
“By the end of the week we were a couple,” he said.
But Daily Mail Australia has confirmed that Bond and Waterland have split – with Waterland debuting her new boyfriend, James Joseph Asciak, this week.
Left-wing feminist Rosie Waterland was thirty when she met conservative commentator Caleb Bond at the age of seventeen. 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 thirteen-year age difference, sex life 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 told Good Weekend that their political differences fueled their banter and fostered a shared empathy, saying she would “tease him for his pro-monarchy stance” and “we built this unlikely online friendship.”
When Waterland, now 37, visited Adelaide from Sydney in 2019 and Caleb met up to “see if the chemistry translates from typing to talking,” they got a room in a hotel.
“He was 20 at the time and the skinny teenager in his name photo was gone,” she told GW.
‘He had grown a beard, had grown fuller and had a glow. The banter translated and we’ve been a couple ever since.
Waterland said they disagreed on most things, including how to dress and politics
‘We are an odd couple. He wears a shirt, cufflinks, tie, suit and tweed blazer with pocket square. I wear T-shirts. Caleb doesn’t have one; he says they are unworthy.
‘I never thought I would 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 big arguments, albeit respectful ones.”
In the interview, Waterland talked about her difficult childhood ‘of abuse and neglect’.
‘My parents were alcoholics and I lived in more than a hundred homes, including foster homes.
‘My post-traumatic stress disorder is largely under control, but last year I was hospitalized three times. We started fighting a lot. He said: “It feels like I’m dating a different person. The Rosie I met is gone.”
Waterland said Bond would reassure her if she was triggered.
Bond said in the interview, 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 hotel room in Adelaide during the Covid pandemic, he drove to Sydney and “had no choice but to move in with her”.
He said they were “both stubborn” but that “butts 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 end up in the same stadium, even though the path we take may be different. I’m not sure who that bothers more: her or me.’
It is believed that Waterland and Bond split ‘about six months ago’ – shortly after the article was published – but they remain on good terms.
“It was an amicable breakup,” the source said.
On Thursday, Waterland posted a photo on Instagram of herself kissing James Joseph Asciak, her new boyfriend, as they sat in the back of a camper.
The couple met when Asciak made a drawing of Waterland as Polly Pocket, the small dolls marketed by Barbie manufacturer Mattel that became all the rage in the 1980s.
Waterland and her new boyfriend James Asciak go 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 in love with a boy who takes a picture of you as Polly Pocket and conveniently has a camper.”
She said this was “good if you wanted to escape on a road trip to try every local bakery between Sydney and Melbourne.”
‘Stay tuned for all the cake/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 out of his house and into his camper a year ago “and set out on an indefinite adventure around Australia.”
‘It has been a life-changing experience to find out who I am outside of work, to like myself a little more and to explore the unknown and unexpected.
‘Nothing more unexpected than luring @rosiewaterland into her Polly Pocket house, and having it ignite a pretty good relationship, and make me want to be part of the real world again.
‘We’re currently meandering from Sydney to Melbourne (eating our way through vanilla slices and cakes) and would love to visit you soon!
“So yeah, I guess the moral of the story is that if you like someone, draw a picture of them, and it will all turn out quite nicely… and give you someone to share the next adventure with. ‘