Jackie “O” Henderson, the Australian radio host, has most recently been linked to Sydney pilot and DJ Richard Ryan, after the pair were photographed kissing at her Clovelly home in 2025.

Quick Scoop: Who Is Jackie O Dating?

  • Multiple Australian outlets have reported that Jackie O was seen in an intimate moment on her balcony with a man identified as Richard Ryan, a pilot and DJ known in Sydney’s eastern suburbs.
  • Photos showed them kissing and cuddling, with reports describing him as a “big name” around the eastern suburbs social scene.
  • These reports frame Richard as her “new boyfriend” or “new romance,” but Jackie herself has not given a long, detailed public confirmation beyond being photographed together.

What’s Actually Confirmed (And What Isn’t)

Public information suggests:

  1. She has been spotted in a romantic context with Richard Ryan (kissing, affectionate body language).
  1. Articles and magazine pieces now refer to him as her new partner or boyfriend and fold this into a narrative of her “fresh chapter” in life post‑divorce and post-2024 personal struggles.
  1. Jackie has historically pushed back on dating rumours when they were wrong (for example, with model Jack Tyerman, where she clearly said “no, he’s not my boyfriend,” calling him just a friend).

Because relationship labels can change quickly and celebrities sometimes keep details private, the safest up-to-date description is: she is widely reported to be dating Richard Ryan, though the exact status and label of the relationship at this exact moment haven’t been spelled out in detail by Jackie herself.

A Bit of Recent Context

  • After splitting from her ex-husband Lee Henderson in 2018, Jackie has spoken a lot about enjoying being single and slowly re‑entering the dating world.
  • Through 2023–2024 she was linked by gossip columns to younger model Jack Tyerman, but she publicly denied that he was her boyfriend, stressing they were just friends despite being seen out together.
  • In 2024 she described her approach as wanting to have fun, go on dates, but not desperately “hunt” for “the one.”
  • By late 2024 and into 2025, she talked about hitting a kind of personal reset: opening up about past painkiller addiction, focusing on her health, and letting love “cross her path” rather than chasing it, which lines up with the timing of this new romance.

Important Note

Celebrity dating lives move fast. Articles from late 2025 present Richard Ryan as her current partner, but relationship status can change without immediate public reporting. For the latest news, it’s always worth checking very recent interviews or social posts, since Jackie herself has shown she will correct the record when rumours go too far.

Information gathered from public forums or data available on the internet and portrayed here.