509: The 99 Rule With Jessica O’Reilly

Jessica O’Reilly is a sex and relationship expert, keynote speaker, television personality and host of the Sex with Dr. Jess The 99 Rule With Jessica O’Reillypodcast. A sought-after speaker, Dr. Jess travels extensively to engage with audiences large and small. From couples’ retreats in the Caribbean to academic conferences in the Great White North, she puts clients and workshop participants at ease with her gentle humour, thorough subject knowledge and friendly disposition.

Jessica shares her insights on what confidence is to her and what she does to keep on increasing it.  She also shares the one rule she goes by that helps her in journey to self confidence.


Jessica O’Reilly is a sex and relationship expert, keynote speaker, television personality and host of the Sex with Dr. Jess podcast.

Cultural Background

Jessica is of Chinese and Jamaican descent.

Favorite Self Confidence Quote

Consider the source.

Consider the source.

Definition of Self Confidence

Self confidence is ultimately involves liking yourself.  The more you like yourself, the more you will be open to liking others.

Her Life Before the Discovery of Self Confidence

For Jessica, confidence isn’t something you have, its more fluid than that.  She has times where she exudes confidence and times where she lacks confidence.  Confidence shifts and its not something you possess, but something you cultivate.

The “AHA” Moment

For Jessica, it was going to a nude beach.  Seeing so many body types and being comfortable in their own skin helped her have confidence with her own body and learned not to complain about her body .

She goes by the 99 rule, will I care about this when I’m 99?

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Her Life After the Discovery of Self Confidence

Life is good for Jessica.  She is most grateful for her health, relationships and security along with a range of other experiences.  She is aware of her privilege.

The One Self Confidence Tip For the Listener

Go easy on yourself.

Interview Links

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