Jack Tyerman, Jackie O’s former toy boy, announces first child with girlfriend Asha Dillon

Jack Tyerman, 31, the tradie long dubbed Jackie 'O' Henderson's former toy boy, has announced that he and his girlfriend, Asha Dillon, are expecting their first child. The news came via an Instagram post on Sunday, where Tyerman shared a series of photos with Dillon, one image showing her cradling a growing baby bump while wearing a bikini top. The caption read “Mum and Dad summer 26,” signaling the couple’s excitement for their impending arrival. The post adds a new chapter to a relationship that has been publicly documented since Dillon made their romance Instagram official in July of the previous year.

Asha Dillon and Tyerman publicized their relationship online in July 2024, and their posts since then have drawn a mix of congratulatory messages from followers and social-media chatter about the pair’s pairing. The couple’s public appearances and updates have kept them in the entertainment conversation, even as both have pursued separate professional paths. The pregnancy announcement appears to be Tyerman’s first major life event of this kind since the relationship moved from social media updates to a more private footing.

The couple’s relationship has long been a topic of public interest because Tyerman was previously linked to Henderson, the KIIS FM host known for The Kyle and Jackie O Show, in August 2023 after he was seen at Henderson’s luxury Sydney residence. While the pairing was initially described as dating, coverage over time suggested the dynamic had shifted, with some insiders implying tensions arose over Tyerman being mentioned in Henderson’s forthcoming autobiography. A Daily Telegraph insider claimed that Tyerman was upset about how he appeared in the book, noting that while the specifics could be identified only by those close to the pair, he knew the work centered on him. The ongoing narrative led to a quiet distancing: Henderson and Tyerman unfollowed each other on Instagram after the book’s release, and they were last seen publicly together at a May 2024 dinner at Restaurant Hubert in Sydney.

Henderson has publicly addressed the relationship on air, telling co-host Kyle Sandilands on KIIS FM’s The Kyle and Jackie O Show that she was not describing Tyerman as her boyfriend and that the two were simply friends at the time. She described Tyerman as a good friend she knows through mutual connections and said they did not meet through a dating app. Henderson’s comments reflected a broader pattern in entertainment reporting, in which flirtations of the past are revisited as both individuals move forward in their careers.

In the months since, the two have largely kept separate public profiles, with Henderson continuing to host her show and Tyerman pursuing his own professional interests. The pregnancy news therefore arrives as a personal milestone for Tyerman and Dillon, distinct from the public-interest arc that has surrounded Henderson and her circle. While there is no indication of how this development might affect the broader media narrative around Henderson, the couple’s announcement underscores how personal milestones in the lives of public figures can become moments of public fascination that endure beyond the original headlines.

As with previous reporting on this circle, the core details remain: Tyerman confirming the pregnancy on social media, Dillon visibly sharing her journey, and the public tracing of a relationship that began in the glare of online visibility and has since evolved into a private, forthcoming family chapter. The episode reflects a broader cultural interest in the intersections between celebrity culture, personal life, and social media, where headlines frequently pivot on evolving relationships and life events rather than on career milestones alone.