

What Makes a Relationship Inevitable? | Sasha Chapin & Cate Hall
Feb 21, 2025
Sasha Chapin is a writer and co-founder of a perfume company, while Cate Hall is a former professional poker player and CEO of a foundation. They discuss the concept of radical honesty in relationships and how the Enneagram can illuminate personality differences. Their conversation humorously navigates their contrasting backgrounds, exploring commitment versus connection. They also reflect on evolving gender roles and envisioning future parenthood, emphasizing growth, trust, and the beauty of embracing vulnerability in love.
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Whirlwind Romance?
- Sasha Chapin connected with Cate Hall online after she tweeted about her dating priorities.
- Their first date involved Sasha moving into Cate's apartment for a week, and they were engaged within three months.
Initial Incompatibility
- Despite the quick engagement, Sasha and Cate's relationship wasn't easy initially.
- They were very different people, which led to awkwardness and communication challenges in the first few months.
Early Challenges and Inevitability
- Sasha made comments early in the relationship that horrified Cate, such as saying he'd never date a vegan (which she was at the time).
- Despite these differences, both felt a sense of inevitability about their relationship.