Jackie O New Boyfriend: Latest Relationship Update

Multiple Australian media reports and public sightings have linked Jackie O’s new boyfriend to Richard Ryan. The popular KIIS FM radio personality was first romantically linked to the Sydney-based charter pilot in 2025 when the pair were spotted together. It marked one of Jackie’s most high-profile romantic connections since her separation from Lee Henderson. Although Jackie has kept the romance largely private, the relationship has attracted significant interest from fans across Australia.

Jackie O has been one of Australia’s most recognisable media personalities for a long time. Her openness about life, family and dating has helped create a strong connection with listeners, and news about her personal life is a frequent source of public interest.

Who is Jackie O’s new boyfriend?

Jackie O has been romantically linked to Sydney-based charter pilot, DJ and marketing professional Richard Ryan.

The relationship first became public in September 2025 when the pair were photographed kissing outside Jackie’s Sydney home. Soon afterwards, they were seen spending time together in Bondi and other parts of Sydney, prompting widespread media coverage.

Unlike Jackie, Richard generally stays away from the public spotlight. Despite the attention surrounding his connection with one of Australia’s biggest radio personalities, he has maintained a relatively private life.

Both Jackie and Richard have kept a low profile on their relationship, so there hasn’t been a lot of media attention.

Who is Richard Ryan?

Richard Ryan works as a professional charter pilot in Sydney and has also worked as a DJ and marketing professional.

Although he is not a celebrity himself, friends have described him as someone with a relaxed personality who enjoys outdoor activities, travel and spending time with family and friends.

Since becoming linked with Jackie O, Richard has largely avoided interviews and public discussions about their relationship.

How did Jackie and Richard meet?

Exactly how Jackie O and Richard Ryan first met has not been publicly detailed.

Reports suggest they became acquainted through mutual social circles in Sydney before beginning a relationship. Jackie has not publicly discussed the early stages of their romance, choosing instead to keep that part of her personal life private.

Jackie O’s previous marriage

Before dating Richard Ryan, Jackie was married to British photographer Lee Henderson.

The couple married in 2003 after several years together. During their marriage they welcomed their daughter, Kitty, who remains the centre of Jackie’s life.

In 2018, Jackie announced that she and Lee had separated after approximately 18 years together. Despite ending their marriage, they have continued to co-parent their daughter respectfully.

Jackie has often spoken positively about maintaining a healthy relationship for Kitty’s benefit.

Dating after divorce

Jackie has spoken openly about the challenges of returning to dating after her separation.

On several occasions, she has discussed trying dating apps and gradually becoming more comfortable with meeting new people. Rather than rushing into another serious relationship, Jackie focused on balancing her demanding career, motherhood and personal life while rebuilding her confidence.

Her openness about dating later in life has resonated with many Australians experiencing similar situations.

Dating rumours before Richard Ryan

Before her relationship with Richard Ryan became public, Jackie was linked with several men.

Jack Tyerman

Jack Tyerman became the subject of dating speculation after being seen with Jackie on multiple occasions.

Jackie later addressed the rumours herself, explaining they were simply friends and confirming they were not romantically involved.

Daniel Cartwright

Neighbour Daniel Cartwright was also linked with Jackie after they were photographed together.

Once again, Jackie clarified publicly that there was no romantic relationship.

Adam Muir

Former Newcastle Knights player Adam Muir was another name connected to Jackie after they spent time together during 2025.

Neither party confirmed a relationship, and the reports remained speculative.

Jackie O’s daughter remains her priority

Jackie has frequently spoken about her close relationship with her daughter, Kitty.

Despite maintaining a demanding career in Australian media, family remains an important part of her life. Jackie regularly shares funny and relatable parenting experiences with her radio listeners.

She has also indicated that any serious relationship needs to fit comfortably into the life she has built with her daughter.

Career success continues

While Jackie O’s relationship receives media attention, her broadcasting achievements remain the foundation of her success.

She has spent decades at the top of Australian radio, interviewing international celebrities, hosting television programs and building one of the country’s most successful entertainment brands.

She has stayed popular with Australian audiences by being able to combine professional achievement with being honest about the problems of life.

Conclusion

Jackie O’s new boyfriend has attracted considerable public interest, but the popular broadcaster continues to maintain a degree of privacy around her personal life. Richard Ryan has become one of her most prominent romantic connections since her separation from Lee Henderson, although Jackie has avoided turning the reported relationship into a public spectacle.

To many Australians, Jackie is still appreciated for her stellar broadcasting career but also for her honesty, resilience and ability to negotiate life after divorce while remaining dedicated to her family and work.