You Keep Dating the Same Person Over and Over

Dec 23, 2025

Emily sits down with Amy Chan, founder of Renew Breakup Bootcamp and author known for her expertise in overcoming breakups. They delve into the reasons we repeat dating patterns, emphasizing that emotional types, not physical traits, dictate our choices. Amy’s unique 12-person dating experiment encourages clients to step outside their comfort zones. They discuss transforming breakups into growth opportunities, recognizing red and green flags in partners, and the importance of emotional readiness in relationships. Tune in to reframe your dating journey!

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ANECDOTE

Entrepreneur Falls For A 9‑To‑5 Partner

One client insisted on only dating entrepreneurs but met a nine-to-five partner during the experiment.
She's been with him three years, showing how dating outside your type can change outcomes.

INSIGHT

Type Is An Emotional Pattern

Your "type" is often an emotional pattern, not physical traits, driven by familiarity.
Strong chemistry can be a red flag if it repeats unhealthy emotional experiences.

ADVICE

Give Attraction Time To Grow

If initial attraction rates 5 or above, give the person another date to gather data via exposure.
Use repeated dates to let attraction grow or fade before deciding.

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EPISODE SUMMARY

In this episode, Emily sits down with Amy Chan—founder of Renew Breakup Bootcamp and author of Breakup Bootcamp: The Science of Rewiring Your Heart—to explore why we keep choosing the wrong partners and how to break the cycle. Amy shares her revolutionary 12-person dating experiment that forces clients to date outside their type, revealing how our "type" isn't about physical traits but the emotional patterns we unconsciously repeat. From spotting unavailable partners to understanding the difference between passionate love and companionate love, this conversation reframes dating as a discovery process rather than a high-stakes audition. Amy breaks down why great daters often struggle in relationships, how to recognize your recurring emotional patterns, and why your best friend you want to make out with might be the person you've been overlooking all along.

In this episode, you'll learn:

• Your "type" is an emotional pattern, not a physical one—by identifying the five main emotions from your last three relationships, you can spot the cycle you keep repeating (like anxiety from chasing unavailable partners) and consciously choose different experiences

• The dating experiment that rewires your brain—dating 12 people outside your type without getting into a relationship removes the pressure of finding "the one" and trains you to be present, recognize how you actually feel with someone, and notice who genuinely treats you well

• Why passionate love fades and what replaces it—the neurochemical high of early romance naturally transitions to companionate love, and understanding this shift helps you stop mistaking familiarity for incompatibility and start building the deeper intimacy that sustains long-term relationships

• The dating funnel approach—treating early dates like lead generation (just asking "Am I having fun? Do I want to see them again?") instead of evaluating someone as your future life partner eliminates job-interview energy and lets authentic connection emerge naturally

• Stop performing, start choosing—moving from "waiting to be chosen" to actively selecting partners based on how they make you feel (not just how they look on paper) puts you in control of your romantic life and attracts people who appreciate your authentic self

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This episode is sponsored by…

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