Why Australian ‘dream girls’ like Jackie ‘O’ Henderson and Pip Edwards are still single despite having the looks, money and success: ‘This is really scary for men’

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Australia is full of accomplished and attractive women, and many, like Jackie ‘O’ Henderson and Pip Edwards, are highly sought-after when it comes to dating.

Even though these women seem to have it all – good looks, financial security, and successful careers – they haven’t found lasting love.

According to relationship expert Kelsey Gaudreault, many successful women may be single because they struggle with being vulnerable and fear letting their guard down, as she told Daily Mail.

As women continue to achieve greater success, we’re starting to desire qualities that men haven’t traditionally offered, she explained.

This is about genuine feelings, feeling secure, and having close relationships. I believe this is a really difficult concept for many men, and it honestly gives me goosebumps to think about how widespread this is.

With so many strong women succeeding, creating successful businesses, and achieving financial independence, we’re encouraging men to connect with their emotions and values. This is a crucial shift we need to see.

Kelsey believes a common reason why accomplished women like Jackie, 50, and Pip, 45, struggle in relationships is that many men are afraid to show their feelings and be open.

But the founder of The House of Union, who is 34 years old, also points out that women sometimes create similar barriers, leading to misunderstandings between men and women.

She notes that Jackie Kennedy Onassis and Pip Edwards both embody a captivating mix of beauty, personality, and drive.

It’s like a shield that hides the person behind her achievements, preventing us from truly seeing her as an individual.

According to the CEO, a woman’s inner qualities are what truly attract a man, more than any outward achievements.

She explains that being emotionally available involves showing your true self, beyond any accomplishments, and letting others see who you really are.

Many people around the world are currently expressing traditionally feminine traits. These women embody what many would consider the ideal of a ‘dream girl’.

It’s easy to believe femininity is about having a certain look – style, fashion, a particular body type. But true embodiment is simply about being yourself, authentically.

She explains they aren’t striving or actively working towards anything – they’re simply existing in the moment.

Embodiment is simply expressing your femininity in the present moment, without trying to achieve any specific result. It’s about being fully present, without an end goal in mind.

Jackie and Pip, like many other prominent Australian women such as Dina Broadhurst, are often featured in the news because of their relationships.

KIIS FM personality and millionaire Jackie O split from her husband, Lee Henderson, in 2018 after 15 years together. They share a 14-year-old daughter named Kitty.

Lee has started a new relationship with Gabriella Motta, a jiu-jitsu instructor with tattoos, while Jackie continues to talk about her difficulties with dating on her radio show.

Pip and Dina, both 50, often appear in the news due to their brief relationships with wealthy and famous men.

Recently, Australians were captivated watching twenty women compete for the affection of Barry ‘Bear’ Myrden on the reality show, The Golden Bachelor.

Most of the attendees left feeling disappointed in love, but the 61-year-old infrastructure engineer went home with CEO Sunny Long—and they’ve already been the subject of breakup rumors.

Kelsey suggests that successful women seeking love should consider whether they allow others to see them as individuals, beyond their accomplishments.

For me, this artist’s work feels incredibly raw and vulnerable. It’s like witnessing someone completely stripped bare, like a queen shedding her royal attire and standing honestly before the one she trusts most. There’s nowhere to hide, no pretense – just pure, unmasked emotion. It’s a really powerful feeling.

Are you willing to show him who you truly are? Take a moment to consider why you hesitate to be vulnerable. What makes you feel valuable and deserving of acceptance?

Does this quality show in all aspects of your life, or is it simply a part of who you are as a woman? I’m referring to your inner self – your spirit, your emotions, everything that lies beneath the surface.

‘That’s what we want to lead with… Can we find worth in our being outside of all the accolades.’ 

Kelsey is a spiritual teacher in Canada who helps people build stronger, more emotionally open relationships.

She inspires her audience to embrace their inner strength as women and guides them in finding wholeness and self-love.

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2025-11-30 13:24