Unlikely media couple Caleb Bond and Rosie Waterland split just weeks after giving an outrageous interview in which they admitted spending ‘five days in a hotel room’ together after first meeting.
Waterland, a feminist writer and comedian, was 30 when she first made contact with Bond, then an outspoken 17-year-old conservative, in 2016. When he was a little older, in 2019, the pair met up in Adelaide and their relationship blossomed.
The pair sat down for a much-talked-about interview with Good Weekend magazine last July, in which Bond, now a Sky News 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 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 Daily Mail has confirmed that Bond and Waterland called it quits not long after their Good Weekend feature hit newsstands – with Waterland debuting her new boyfriend, James Joseph Asciak, this week.
Left-leaning 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’, supplied with permission
Waterland and Bond split after they gave an outrageous interview about their 13-year age gap, their 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 which has now ended
Waterland told Good Weekend their political differences fuelled their banter and fostered a shared empathy, saying she would ‘tease him for his pro-monarchy stance’ and ‘we grew 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 talking’, they got a room at a hotel.
‘He was 20 by then and the skinny teenager from his byline picture was gone,’ she told GW.
‘He’d grown a beard, filled out, had a glow-up. 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’re an odd couple. He wears a shirt, cuff links, tie, suit and tweed blazer with a pocket square. I wear T-shirts. Caleb doesn’t own one; he says they’re undignified.
‘I never thought I’d end up with a man who won’t call himself a feminist.
‘He believes in equality, but claims that the word has been co-opted by extremists. We have raging 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 100 houses, including foster homes.
‘My post-traumatic stress disorder is largely under control but, last year, I was hospitalised three times. We started fighting lots. He said, “I feel like I’m dating a different person. The Rosie I met has gone.”‘
Waterland said if she was triggered, Bond would reassure her.
Bond said in the interview, which was published shortly before their split, that he was into older woman 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 option but to move in with her’.
He said they were ‘both headstrong’ but that ‘butting heads can make you better people’.
‘I don’t like being told I’m wrong, which Rosie does, sometimes, like any good girlfriend,’ he added.
‘It’s surprising how often we land in the same ballpark, though the road we take may differ. Not sure who that disturbs more: her or me.’
It is understood Waterland and Bond split ‘about six months ago’ – soon after the article’s publication – but they remain on good terms.
‘It was an amicable break-up,’ a 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 campervan.
The couple met when Asciak drew a picture of Waterland as a Polly Pocket, the small dolls marketed by Barbie manufacturer Mattel, which became a fad in the 1980s.
Waterland and her new boyfriend James Asciak are setting 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 campervan.’
She said this was ‘right when you would like to escape on a road trip to test out every single local bakery between Sydney and Melbourne.
‘Stay tuned for all the pie/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 had moved out of his home and into his campervan a year ago ‘and set off on an indefinite adventure travelling around .
‘It has been a life-changing experience figuring out who I am outside of my job, liking myself a little more, and exploring the unknown and unexpected.
‘None more so unexpected than drawing @rosiewaterland into her Polly Pocket home, and having that spark the start of a pretty great relationship, and make me want to rejoin the real world again.
‘We’re currently meandering our way from Sydney to Melbourne (eating our way through vanilla slices and pies) and keen 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’ll all work out pretty lovely…. and give you someone to share the next adventure with.’