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In this first Dear Diary segment, Kristen shares journal entries from her 16-year-old self, revisiting a short-lived high school crush full of notes, Skittles, and a sweet cappuccino moment. Through the nostalgia and drama, she reflects on how teenage insecurities—like the fear of rejection and caring too much about others’ opinions—still resonate today.

Join Kristen for laughs, insights, and a trip down memory lane as she explores how the past shapes us. Plus, share your own stories: What insecurities have stayed with you, and which ones have you overcome? Let’s talk about it!

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