28 Things I Wish I Knew at 18 (About Boys, Confidence, Dating, and Self Worth) cover art

28 Things I Wish I Knew at 18 (About Boys, Confidence, Dating, and Self Worth)

28 Things I Wish I Knew at 18 (About Boys, Confidence, Dating, and Self Worth)

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With special guest: my Sister!!! For my 28th birthday, I sat down with my 18-year-old sister to share 28 truths about confidence, dating, boys, people, and being a woman with self-worth.

This conversation moves from chaotic sister humor to the deeper realities of building confidence as a woman. We talk about why most mistakes get made after midnight, how everything feels more dramatic in the dark, and why intensity is not the same thing as compatibility. We unpack the difference between attraction and anxiety, and why calm, secure love can is often the healthiest.

Beyond dating and relationships, we get into the foundations of self-love: choosing your environment wisely, eating consistently, setting boundaries without over-explaining, and remembering that no one is coming to save you. We talk about body image, spotlight syndrome, conquering insecurities, being the average of the people you spend time with, getting to know your mom as a person, and why embarrassment is a choice.

I hope this Mary’s Cup of Tea episode feels like a confidence pep talk from your virtual big sister.

Remember: “The worst thing in the world can happen, but the next day the sun will come up. And you will eat your toast. And you will drink your tea.”

Hope this episode is somehow entertaining and somewhat useful to your self-love journey.

If you’re enjoying our self love podcast, share it with the women in your life! Your support helps spread women empowerment and self-love!

Deepen your self love journey with Mary’s books:

  1. The Gift of Self-Love, an interactive workbook to help you build confidence, recognize your worth, and learn to finally love yourself.
  2. 100 Days of Self-Love, a guided journal with 100 prompts for calming self-criticism and learning to love yourself.

Follow Mary Jelkovsky on IG: @maryscupofteaa and @maryspodcast

Mentioned In This Episode...

Mary’s Self-Love Playlist: maryscupoftea.com/playlist


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