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Dating Dilemmas: Jackie ‘O’ Henderson Discusses Her Biggest Fear After Troubling Relationships

Australian Radio Presenter and TV Show Host, Jackie 'O' Henderson

Jackie O Henderson has recently reflected on her past relationships, shedding light on her previous attraction to certain types of men and how she was often mistreated. On the debut episode of her “Her Best Life” podcast, co-hosted with her manager Gemma O’Neill, Jackie discussed how she endured poor treatment from past partners.

In her candid conversation, Jackie admitted she had not valued herself properly and had accepted subpar treatment. She revealed that her tendency to be a “people pleaser” often led her to take on a caretaker role in her relationships.

Jackie O Henderson humorously recounts her early dating app experiences and her tendency to envision future relationships too quickly

Jackie’s split from ex-husband Lee Henderson, which occurred in 2018 after a 15-year marriage, marked a turning point. She had previously been married to former radio co-host Phil O’Neil for four years, before their divorce in 1999.

On the podcast, Jackie acknowledged her own faults in relationships but emphasized that her focus was always on others’ needs rather than her own. “I was never Mother Theresa,” she remarked, noting that she often neglected her own well-being.

Discussing her past difficulty in standing up for herself, Jackie shared that she struggled to address minor issues in her relationships, preferring to avoid confrontation to keep things comfortable for her partners.

Reflecting on her journey post-divorce, Jackie mentioned the transformative advice from her psychologist about self-love and setting boundaries. She learned that embracing self-care and asserting her needs led to positive changes in her life.

Jackie observed that setting boundaries gradually increased her sense of empowerment and attracted more fulfilling relationships and opportunities. She noted that small actions toward self-respect can eventually lead to personal growth.

After her divorce, Jackie briefly tried dating apps, and she humorously recounted meeting someone she immediately thought was “the one.” Her best friend Gemma recalled Jackie’s excitement and how she had envisioned a future with the person before their first meeting.

Jackie admitted that her early dating experiences often left her feeling exhausted, as she worked hard to appear engaging and pleasant, which was not her true self.

In recent years, Jackie has become a prominent socialite, expanding her circle to include Australia’s elite and even attending a European wedding. Her social network now includes well-known figures like P.E Nation designer Pip Edwards, stylist Jess Pecoraro, and make-up artist Max May.

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