Jackie O’s boyfriend: Who is she dating in 2026?
Jackie O’s boyfriend is a popular search term for Aussies following celebrity news. Jackie “O” Henderson is currently with Sydney charter pilot DJ and marketing executive Richard Ryan. The pair initially gained public prominence in 2025 and have remained together, keeping much of their courtship out of the spotlight. Jackie has been candid about life after her divorce but likes to keep her current relationship private.
Who is Jackie O’s boyfriend?
Jackie O’s partner is Sydney-based charter pilot and DJ and marketing professional Richard Ryan. Jackie is a television and radio person; Richard is not. He has created a profession outside of the entertainment world and normally shuns the spotlight.
He’s remained under the radar publicly but Richard became a household name when he dated one of Australia’s biggest radio personalities. The pair have been photographed together sporadically around Sydney since then.
How Jackie O and Richard Ryan’s relationship became public?
Jackie and Richard In 2025, observers spotted Jackie and Richard hanging out together in Sydney, sparking their initial connection. in 2025 when they were observed hanging out together in Sydney. Their romance made news when the pair were pictured kissing on the balcony of Jackie’s Clovelly house.
Since then they have been seen eating dinners, attending events and hanging out throughout Sydney’s eastern suburbs. But neither Jackie nor Richard shares much about their relationship in interviews or on social media, despite the interest from the public.
Is Jackie O still dating Richard Ryan?
Yes. Based on the latest public evidence, Jackie O and Richard Ryan are still together in 2026.
The couple have maintained a rather discreet relationship. Jackie does discuss dating and relationships on her radio shows occasionally, but she rarely discusses anything personal about Richard. This balance has allowed them to enjoy their relationship outside of the continual public scrutiny.
Who is Richard Ryan?
Richard Ryan has had a successful career outside the entertainment sector.
His professional experience includes:
- Charter pilot
- Professional DJ
- Marketing executive
Friends say he is a private person who prefers to keep out of the limelight. That’s one of the reasons so little personal information about him has been made public.
Jackie O’s previous marriage
Jackie O was previously married to British photographer Lee Henderson before she dated Richard Ryan.
The pair married in 2003 and had a daughter, Kitty Henderson. Jackie and Lee split in 2018 after over 15 years of marriage.
They might not be married anymore but they have managed to stay on good terms as parents and are still putting their efforts into raising their kid together.
Jackie O’s life after divorce
After the split, Jackie candidly shared the challenges she faced in re-entering the dating scene after years of marriage.
Jackie’s KIIS FM breakfast programme was often full of amusing, honest stories about her dating app life, first dates and finding confidence again. Her openness was refreshing to many Australians, speaking to the experiences many people have following divorce.
Over time, Jackie grew more comfortable with her private life and eventually was happy with Richard Ryan.
Jackie O’s successful media career
Jackie O is one of Australia’s most successful television personalities despite her relationship being of public interest.
She has had a great career in radio, television, podcasting, and publishing. She is a big figure in Australian entertainment, thanks to a long-running breakfast radio show that established her as one of the country’s most high-profile broadcasters.
Her ability to connect with audiences via humour, honesty and authenticity has kept her popular for more than 20 years.
Why Australians are interested in Jackie O’s boyfriend?
Jackie O has spoken up about various personal milestones throughout her career, including marriage, motherhood, divorce and dating. When her personal life reaches the news, there is always real intrigue, because listeners have been on her trip for years.
Richard Ryan’s love of solitude has also helped feed curiosity. He’s not like many of the celebrity spouses who desire the media spotlight, so any time they are seen out together, it makes the news.
Conclusion
One of the most searched topics is a Jackie O lover, as Australians continue to follow the media personality’s life on and off TV. Jackie divorced and for a few years she focused on family and her job, but now she seems happy with Richard Ryan. The couple keep their relationship pretty secret but are nonetheless one of Australia’s most discussed celebrity couples.
