In this episode, we look at the very first examples of love we ever witnessed — our parents — and unpack how those relationships quietly shaped our dating preferences, expectations, and blind spots.
Janai shares what it was like growing up with parents who had a fun, wild relationship — a rough-around-the-edges provider father and a working, playful mother — and how watching that dynamic, along with the softness and affection in her mom's later marriage, influenced what she thought love was supposed to look like.
Kelsi opens up about growing up in the aftermath of a volatile, messy divorce, and watching her mother enter relationships with abusive and emotionally immature men. She reflects on how chaos became familiar, and how that familiarity showed up later in the partners she chose.
We talk about how differently we were raised around boys and dating — Janai being taught that relationships were meant to end in marriage, and Kelsi having more openness and curiosity without that same expectation. And yet, despite those differences, we both found ourselves yearning for love and affection… and seeking it in the wrong places, with people who didn't value or appreciate us.
The conversation expands into the importance of dating — not as failure, but as education. Learning yourself. Gaining awareness. Understanding what works for you, not what you were told should work.
We also unpack how people — especially within relationships — try to keep women in boxes. How we're expected to be palatable, ladylike, quiet, agreeable, and "easy" in order to deserve good partners. And how those expectations shape who we pursue, how we show up, and how much of ourselves we're willing to shrink.
If you've ever looked at your dating history and wondered "Why do I keep choosing this?" — this episode is for you.
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