Podcasts > The School of Greatness > Why You Keep Choosing the Wrong Person (And How to Finally Stop) | Faith Jenkins

Why You Keep Choosing the Wrong Person (And How to Finally Stop) | Faith Jenkins

By Lewis Howes

In this episode of The School of Greatness, Faith Jenkins and Lewis Howes explore the foundations needed to build healthy, lasting relationships. Jenkins discusses how self-awareness, emotional maturity, and healing from past wounds enable better partner selection and relationship success. She shares insights from her own journey, including waiting until 42 to marry, and explains why the work done during singleness—developing communication skills, setting clear boundaries, and identifying non-negotiables—prepares individuals for partnership.

The conversation covers practical strategies for evaluating potential partners, including recognizing red flags, examining behavioral patterns, and understanding the value of pre-engagement counseling. Jenkins and Howes discuss why love requires sustained commitment beyond initial feelings, address common pressures that lead people to settle, and emphasize that choosing a life partner is one of the most consequential decisions anyone makes. Throughout, they provide guidance on maintaining high standards and distinguishing between necessary compromises and essential dealbreakers.

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Why You Keep Choosing the Wrong Person (And How to Finally Stop) | Faith Jenkins

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Why You Keep Choosing the Wrong Person (And How to Finally Stop) | Faith Jenkins

1-Page Summary

Self-Awareness, Maturity, and Growth: Foundations for Healthy Relationships

Faith Jenkins and Lewis Howes discuss how self-knowledge, emotional maturity, healing from past wounds, and personal development are essential for building strong, lasting relationships.

Building Self-Knowledge and Emotional Maturity

Jenkins emphasizes using one's twenties to discover personal values and non-negotiables, which leads to better relationship decisions later. While initial attraction may spark connection, lasting compatibility comes from shared values and deeper understanding. She highlights the importance of recognizing red flags and distinguishing between necessary compromises and essential dealbreakers.

Jenkins and Howes discuss how emotional maturity enables separating feelings from facts, especially during heartbreak. Jenkins learned to acknowledge her pain while recognizing that "this is happening for a reason." Radical acceptance—trusting that relationships sometimes end for reasons not always visible—allowed her to view breakups as opportunities for growth. This mindset shift helped her meet her husband after a significant breakup.

Jenkins warns that unhealed wounds breed cynicism and block healthy love. She stresses the ongoing work of healing: "I had to learn to allow the past to stay in the past. I didn't want someone to come into my life and I make them pay for something they had nothing to do with." Both speakers reflect on how each relationship offers lessons, with Jenkins noting that pain lessened over time as she learned to separate her self-worth from external events.

Jenkins asserts that preparing for partnership begins with intentional self-improvement during singleness. By developing strong communication skills, conflict resolution abilities, and healthy boundaries, she believes one builds the foundation for lasting relationships and becomes more discerning in choosing partners.

Recognizing Red Flags and Patterns

Jenkins and Howes emphasize identifying warning signs and behavioral patterns in potential partners. Jenkins gives the example of someone claiming to be vegan but eating chicken wings—a seemingly minor deception that reveals deeper issues with authenticity and integrity. She stresses that small lies indicate how someone will handle bigger matters.

To understand future actions, Jenkins explains, look at historical behavioral patterns rather than promises. Drawing an FBI profiling analogy, she notes that people might lie, but their patterns don't. Someone with a history of infidelity claiming things will be different should be viewed skeptically unless sustained behavioral change is evident over time.

Digital footprints also reveal values and compatibility. Jenkins recounts declining a blind date after reviewing the person's social media and finding their humor incompatible with her values. She emphasizes that red flags range from major dealbreakers to subtle warnings like dismissive comments or avoidant behavior. Howes adds that while difficult, making decisions with the head rather than the heart ensures warning signs aren't overlooked or rationalized.

Pre-engagement Counseling and Important Conversations

Jenkins and Howes emphasize structured dialogue and counseling before engagement. Jenkins and her husband underwent pre-engagement counseling, which allowed them to explore incompatibilities before public announcements or wedding planning created pressure to proceed despite doubts. She notes that counselors asked unexpected questions about everything from daily routines to life goals, ensuring nothing essential was overlooked.

Jenkins highlights understanding how partners have healed from past relationship pain, explaining that unhealed hurt can foster codependence and misplaced expectations. Openly discussing daily responsibilities and expectations prevents silent resentment, while aligning life goals—including where to live and career ambitions—ensures both partners feel secure moving forward.

Premarital counseling cultivated conversations about love languages, conflict resolution, and commitment philosophy. Howes references the Five Love Languages framework in clarifying compatibility, while Jenkins emphasizes that identifying whether partners' approaches align reduces future conflicts rooted in misunderstanding or misaligned expectations.

Love as a Commitment Rather Than a Feeling

Jenkins explores the difference between falling in love and the sustained work required for long-term relationships. She asserts that "it's easy to fall in love...it takes work to stay there." The intense feeling fades over time, but true commitment means actively choosing to stay engaged even after the emotional high wanes.

Jenkins highlights how life inevitably evolves, causing feelings of connection to fluctuate. In tough seasons, steady commitment carries love through. She compares relationship maintenance to tending a garden: "If you maintain and you take care of your yard...you have to mow the lawn, take care of the grass, fertilize it, pull out the weeds." Consistent effort—communication, appreciation, and attentiveness—keeps partnerships strong.

Jenkins warns against the narrative that "meant to be means it's easy," explaining that this expectation sets couples up for disappointment. Real love is proven when one chooses their partner through boredom, conflict, stress, or change, building lasting love rooted in commitment rather than transient feeling.

Avoiding Settling and Maintaining High Standards

Jenkins waited until 42 to marry, despite external pressures. She and Howes note that research shows significantly lower divorce rates for those who marry later, as the intervening years allow for personal growth and clarity about true needs. Howes reflects that if he'd married anyone from previous relationships, he would have divorced.

Both stress that choosing a partner is among life's most consequential decisions. Marriage affects daily routines, experiences, and profoundly influences children if a couple has them. Jenkins urges careful evaluation and warns against rushing due to pressure or loneliness.

Settling often stems from loneliness, fear of missing out, low self-worth, or external timeline pressure. Jenkins discusses the subtle shame from prolonged singleness and emphasizes addressing internal wounds rather than seeking to "not be single." She contends that marriage doesn't change fundamental character—expecting a partner to change after marriage leads to disappointment. Howes agrees, cautioning against choosing someone for their potential rather than their reality.

Jenkins stresses that valuable partners are distinguished by character, values, and commitment. The true measure is how they treat others, especially those from whom they have nothing to gain. Setting clear boundaries and identifying non-negotiables is critical for long-term satisfaction. Jenkins advises it's okay—and necessary—to have standards and leave relationships involving emotional abuse or repeated hurt, as remaining normalizes poor treatment while leaving allows for healing and reaffirms self-worth.

1-Page Summary

Additional Materials

Counterarguments

  • The emphasis on self-knowledge and personal development as prerequisites for healthy relationships may overlook the fact that many successful relationships are built and grow even as individuals continue to discover themselves and heal over time.
  • The idea that marrying later leads to lower divorce rates is supported by some research, but other studies suggest that relationship satisfaction and stability depend on a variety of factors, including cultural context, support systems, and individual circumstances, not just age.
  • Relying heavily on identifying red flags and patterns may lead to excessive caution or mistrust, potentially causing individuals to prematurely dismiss partners who could be compatible with time and communication.
  • The focus on structured counseling and pre-engagement dialogue may not be accessible or culturally relevant for all couples, and some relationships thrive without formal counseling.
  • The assertion that marriage does not change fundamental character may not account for the ways in which people can and do grow, adapt, and change within committed partnerships.
  • The recommendation to make decisions with the head rather than the heart may undervalue the importance of emotional intuition and the role of feelings in building connection and empathy.
  • The idea that settling is always negative may not consider that compromise and acceptance of imperfections are inherent in all relationships, and what constitutes "settling" can be subjective.
  • The focus on maintaining high standards and non-negotiables could potentially lead to unrealistic expectations or difficulty finding a partner, especially if standards are rigid or inflexible.
  • The use of digital footprints to assess compatibility may not always provide an accurate or complete picture of a person's values or character, as online personas can differ from real-life behavior.

Actionables

- You can create a personal relationship audit by listing your top five values and non-negotiables, then reviewing your current or past relationships to see where they align or conflict, helping you make more intentional choices moving forward.

  • A practical way to strengthen emotional maturity is to keep a feelings vs. facts journal during emotionally charged moments, writing down what you feel and what you objectively know, so you can practice separating emotions from reality before making decisions.
  • You can set up a monthly self-check-in where you rate your communication, boundaries, and conflict resolution skills on a scale of 1–10, then choose one area to focus on improving with a specific, small action (like initiating a difficult conversation or saying no to a request) before the next check-in.

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Why You Keep Choosing the Wrong Person (And How to Finally Stop) | Faith Jenkins

Self-Awareness, Maturity, and Growth: Foundations for Healthy Relationships

Faith Jenkins and Lewis Howes discuss the crucial role of knowing oneself, emotional maturity, healing from the past, and self-development in building strong, lasting relationships. Drawing from Faith Jenkins’ personal experiences and observations, they outline how these foundational qualities lead to healthier partnerships and more conscious choices.

Know Yourself to Identify True Desires in a Partner

Faith Jenkins emphasizes the importance of self-knowledge in one’s twenties. She encourages using this period to discover likes, dislikes, values, and non-negotiables, laying the groundwork for making better relationship decisions later. Jenkins notes that initial physical attraction may lead to connection, but enduring compatibility comes from shared values and deeper understanding. She describes her own journey in clarifying core values and learning what she was or was not willing to compromise on, clarifying that non-negotiables are acceptable and necessary.

Learning about oneself allows for more conscious dating and clearer vision in partnership, reducing the risk of settling for incompatible people. Jenkins also highlights the importance of recognizing red flags, learning the difference between compromises and essentials, and making decisions accordingly.

Emotional Maturity: Separating Feelings From Facts, Accepting Difficult Circumstances With Radical Acceptance

Jenkins and Howes discuss how emotional maturity enables individuals to distinguish between emotional pain and objective reality, especially during heartbreaks. Jenkins recounts how, with maturity, she learned to separate her feelings from the facts: “My feelings are hurt, and it's okay for me to feel this hurt, I'm human. But the fact is, this is happening for a reason.” She highlights that while pain is inevitable, additional suffering often stems from reactive behaviors and internalizing events.

Radical acceptance is key—acknowledging that relationships sometimes end for reasons not always visible and trusting that better things may come. Jenkins shares that adopting this mindset allowed her to approach breakups as opportunities for growth and new beginnings. She consciously chose to view the end of a relationship as opening the door for the right partnership, expressing faith that “something better is coming, even if unseen.”

Her own transformation is evident in how she handled a significant breakup: rather than dwell in pain or bitterness, she accepted the ending, committed to letting go, and opened herself up to new possibilities, which led her to meet her husband.

Heal Past Relationship Wounds Before New Partnership

Jenkins warns that unhealed heartbreak and betrayals breed cynicism, which can block healthy love. Fear of future hurt may masquerade as self-protection but often only poisons perspective and undermines openness to new relationships. Jenkins admits to periods of cynicism and jadedness, acknowledging the inner work required to break these patterns.

She stresses that healing from the past is non-linear and demands conscious effort: “I had to learn to allow the past to stay in the past. I didn't want someone to come into my life and I make them pay for something they had nothing to do with...I had to decide how I wanted to live my life and what perspective I really wanted to have.” Jenkins articulates the need for ongoing self-reflection and a commitment to emotional health, so new partners are not burdened by wounds from prior relationships.

Emotional Maturity Grows Through Relationships and Lessons

Both Jenkins and Howes reflect on the growth that emerges from the end of relationships and the learning that each experience brings. Jenkins shares that with each dating experience, including rejections, the resulting pain lessened over time as she internalized lessons from each situation. She recounts an early experience where she misinterpreted the reason for a rejection, later realizing it had nothing to d ...

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Self-Awareness, Maturity, and Growth: Foundations for Healthy Relationships

Additional Materials

Counterarguments

  • The emphasis on self-awareness and personal growth as prerequisites for healthy relationships may overlook the fact that many successful relationships are formed and thrive even when individuals are still discovering themselves or have unresolved issues.
  • The idea that healing from past wounds must be complete before entering a new relationship may be unrealistic, as healing can be an ongoing process that occurs within supportive partnerships.
  • Focusing heavily on self-improvement and readiness could lead to perfectionism or avoidance of relationships due to feeling perpetually unprepared.
  • The notion that emotional maturity is necessary to separate feelings from facts may not account for cultural or individual differences in emotional expression and processing.
  • The belief that one must become the "right partner" before attracting a lasting relationship may inadvertently pla ...

Actionables

  • You can create a weekly self-check-in ritual where you write down recent situations that triggered strong emotions, then identify whether your reaction was based on facts or feelings, helping you practice emotional maturity and separate emotional pain from unnecessary suffering.
  • A practical way to clarify your relationship non-negotiables is to draft two lists: one of qualities or values you absolutely need in a partner, and another of things you’re willing to compromise on, then review these lists before each date to stay grounded in your true priorities.
  • You can set up a “growt ...

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Why You Keep Choosing the Wrong Person (And How to Finally Stop) | Faith Jenkins

Recognizing Red Flags and Patterns in Potential Partners

Faith Jenkins and Lewis Howes discuss the importance of identifying red flags and consistent behavioral patterns in potential partners. They emphasize that dismissing small warning signs can allow larger problems to unfold in relationships.

Lies and Inconsistencies Reveal Deeper Character Issues and Should Not Be Dismissed

Faith Jenkins gives the example of someone who claims to be vegan but is later seen eating chicken wings on Snapchat. This seemingly minor deception highlights a tendency to feel unsafe being authentic and a compulsion to project a false image to impress others. Such small lies matter; Jenkins notes that if someone cannot be honest about minor things, it likely indicates how they will handle bigger matters. Jenkins stresses that these subtle inconsistencies provide insight into a person's integrity and character.

Past Behavior Predicts Future Better Than Promises

Jenkins explains that to understand someone’s future actions, one should look at their historical behavioral patterns. Drawing an analogy to how the FBI profiles individuals, Jenkins says people might lie, but their patterns do not. Observing how someone has acted in previous relationships or at work delivers more reliable data about their character than their verbal assurances about change. For instance, a person with a history of infidelity who claims things will be different should be considered a significant red flag, as words about improvement must be questioned if not matched by actions.

Align Actions and Consistency With Personal Claims or Transformation

Jenkins advises to trust actions over words, especially when they do not align. When someone acknowledges mistakes from their past but claims to be living differently now, Jenkins encourages a healthy skepticism—look for concrete evidence of sustained behavioral change over time, not just promises made during the dating phase. She stresses that genuine transformation is demonstrated by a long-term shift in actions, not just by talking about change.

Digital Behavior Reveals Values, Humor, and Character

Digital footprints provide insight into values and compatibility. Jenkins recounts declining a blind date after reviewing the person’s social media and finding their humor incompatible with her values. She asserts that social m ...

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Recognizing Red Flags and Patterns in Potential Partners

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Clarifications

  • "Red flags" are warning signs indicating potential problems or unhealthy traits in a relationship. They can be behaviors, attitudes, or patterns that suggest disrespect, dishonesty, or incompatibility. Recognizing red flags early helps prevent emotional harm and relationship failure. They vary from obvious issues like cheating to subtle signs like consistent avoidance or dismissiveness.
  • Projecting a false image means presenting oneself in a way that is not true to their real personality or values. People do this to gain approval, avoid judgment, or fit into social groups. It often stems from insecurity or fear of rejection. Over time, this behavior can harm trust and authenticity in relationships.
  • The FBI uses behavioral profiling to predict future actions based on past patterns. This method analyzes consistent behaviors rather than isolated statements. In relationships, observing someone's history reveals their true character more reliably than promises. Thus, past actions serve as a practical guide to anticipate future behavior.
  • Personal non-negotiables are core values or boundaries that a person refuses to compromise on in a relationship. They reflect what is essential for one's emotional well-being and respect. These can include things like honesty, loyalty, or lifestyle choices. Knowing them helps individuals avoid relationships that conflict with their fundamental needs.
  • Social media posts often reflect a person's interests, beliefs, and sense of humor, which are key parts of their identity. Patterns in online behavior, like how they treat others or what they share, can indicate their values and priorities. Incompatibilities in these areas may signal potential conflicts in a relationship. Thus, digital behavior acts as a window into someone's character beyond face-to-face interactions.
  • Verbal promises of change are statements someone makes about how they intend to behave differently in the future. Genuine behavioral transformation requires consistent, observable actions over time that align with those promises. Change is proven through repeated patterns, not just words or temporary effo ...

Counterarguments

  • Overemphasizing minor inconsistencies or "red flags" can lead to unnecessary suspicion and prevent the development of trust and intimacy in relationships.
  • People may tell small lies or present themselves differently in early dating due to nerves, social pressure, or a desire to impress, which does not always indicate deeper character flaws.
  • Past behavior is not always a definitive predictor of future actions, as individuals can and do change, especially with self-awareness, therapy, or life experiences.
  • Relying heavily on digital footprints or social media activity may misrepresent a person's true character, as online personas are often curated and do not always reflect offline values or behavior.
  • Focusing too much on logic and minimizing emotional input can result in overly rigid decision-making and may overlook the impor ...

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Why You Keep Choosing the Wrong Person (And How to Finally Stop) | Faith Jenkins

Relationship Preparation Through Pre-engagement Counseling and Important Conversations

Relationship experts Faith Jenkins and Lewis Howes emphasize the critical role of structured dialogue and counseling prior to engagement and marriage. Their experiences reveal that thorough preparation and open conversation lay the groundwork for a healthy, sustainable partnership.

Pre-engagement Counseling Finds Incompatibilities Before Engagement Announcements

Jenkins and her husband underwent pre-engagement counseling before deciding to get engaged. This allowed them the freedom to explore possible incompatibilities before making public announcements or planning a wedding. Jenkins argues that once engagement is public and wedding plans are underway, discovering problems can feel overwhelming or embarrassing, causing many to proceed despite doubts. Pre-engagement counseling provided an opportunity to end the relationship before such pressures mounted, ensuring both partners could walk away without social or emotional consequences if core misalignments emerged.

Counselors Ask Unexpected Questions, Aiding Exploration of Unconsidered Compatibility Dimensions

Jenkins notes that, while she brought her own questions to counseling, having a professional guide surfaced topics she hadn’t considered, broadening the scope of compatibility exploration. The counselor asked about everything from daily routines to deeper life goals, helping both partners think through the practical and emotional realities of a future together. These unexpected questions ensured nothing essential was overlooked.

Healing From Past Relationships Shows how Your Partner Handles Trauma

Jenkins highlights the necessity of understanding how partners have healed from past relationship pain. Both she and her husband discussed unresolved issues from previous relationships, which helped them identify any potential triggers for harmful behavior. Jenkins explains that bringing unhealed hurt into a new relationship can foster codependence and misplaced expectations. The healing journey, she says, is ongoing and must be supported by honest, compassionate communication. It was in the early months of her marriage, during challenging times like the pandemic, that Jenkins witnessed her husband's positive response to adversity, which deepened her confidence in their partnership.

Avoiding Resentment Through Open Discussion of Life Roles and Responsibilities

Openly discussing daily responsibilities and expectations is vital for preventing silent resentment. Jenkins shares that pre-engagement counseling required her and her husband to explore how they would handle time together, household tasks, and raising children. These talks surfaced assumptions that, if unspoken, might have led to disappointment or frustration. Howes reinforces that uncommunicated expectations inevitably result in unmet needs and growing resentment, emphasizing that even long-term projections—six months, six years, or more—need frank discussion.

Aligning Life Goals and Career Aspirations For a Compatible Future

Jenkins advises that couples must align their visions for the future, includ ...

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Relationship Preparation Through Pre-engagement Counseling and Important Conversations

Additional Materials

Counterarguments

  • Some couples may find that structured counseling and formal dialogue feel artificial or unnecessary, preferring organic communication and growth within the relationship.
  • Pre-engagement counseling may not be accessible or affordable for all couples, potentially privileging those with more resources.
  • Not all incompatibilities can be identified through counseling or structured conversations; some issues only emerge through lived experience over time.
  • The pressure to "find problems" in counseling could lead some couples to overanalyze or create issues that might not be significant in daily life.
  • Cultural or religious backgrounds may offer alternative approaches to relationship preparation that do not involve formal counseling.
  • Some individuals may feel uncomfortable sharing deeply personal issues with a third-party counselor, which could hinder open communication.
  • The emphasis on identifying and resolving all potential issues before engagement may create unrealistic expectations of certainty and control in ...

Actionables

  • You can set up a monthly “future check-in” with your partner where you each write down your five-year and ten-year visions separately, then swap papers and discuss any surprises or mismatches, helping you spot and address misalignments before they become issues.
  • A practical way to uncover hidden expectations is to each make a list of daily, weekly, and yearly routines you imagine sharing, then compare and talk through any differences, such as who handles chores, how weekends are spent, or how holidays are celebrated.
  • You can create a “rel ...

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Why You Keep Choosing the Wrong Person (And How to Finally Stop) | Faith Jenkins

Love as a Commitment Rather Than a Feeling

Faith Jenkins explores the difference between falling in love—an easy, fleeting experience—and the sustained work required to remain loving and connected in a long-term relationship. Jenkins frames lasting love as an ongoing commitment rather than just an emotional high.

Lasting Love Requires Daily Commitment, Not Just Initial Attraction

Jenkins asserts that "it's easy to fall in love...it takes work to stay there." The intense "in love" feeling fades over the course of a long-term partnership. True commitment means actively choosing to stay engaged and devoted to one's partner even after the emotional high of early love wanes. Jenkins explains that maintaining a relationship over time requires a shared commitment to growth—for both individuals and for their bond—emphasizing that success in marriage comes from "being committed to the same commitment."

Separating Love's Feeling From Its Commitment Helps Navigate Tough Seasons Without Abandoning the Relationship

Jenkins highlights how people's lives inevitably evolve due to careers, family, health, and personal growth, causing feelings of connection to fluctuate. In tough seasons—marked by stress, change, or conflict—feelings may be less intense, but steady commitment is what carries love through. Letting go of the idea that marriage should remain unchanged helps couples embrace the journey and stay dedicated even during challenging times. Instead of treating disconnection or hardship as signs to end the relationship, seeing love as an ongoing choice allows couples to navigate difficulties and maintain their bond.

Nurturing a Relationship Is Like Tending a Garden—Needs Consistent Attention

Jenkins compares long-term care in relationships to tending a garden: "If you maintain and you take care of your yard...you have to mow the lawn, take care of the grass, fertilize it, pull out the weeds." Consistent, intentional effort—communication, small acts of appreciation, and attentiveness—are vital for growth and health in relationships. Skipping this "day-to-day" work leads to stagnation. Jenkins stresses that "being on autopilot" does not sustain relationships; regular nurturing and explicit appreciation are what keep the partnership strong through every season, rain or shine.

Love As Commitment: Serving and Sacrificing For Partner's Wellbeing

Jenkins draws on marriage as an example, ...

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Love as a Commitment Rather Than a Feeling

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Counterarguments

  • Emphasizing commitment over feelings may risk encouraging people to stay in unhealthy or unfulfilling relationships, potentially overlooking issues like incompatibility or emotional neglect.
  • The idea that love is primarily a decision or commitment can downplay the importance of emotional connection and mutual attraction, which are also vital for many people’s relationship satisfaction.
  • Some psychological research suggests that both commitment and emotional intimacy are necessary for long-term relationship success; focusing too heavily on commitment alone may neglect the role of affection and passion.
  • The analogy of tending a garden may not resonate with everyone, as some individuals or couples may find that their relationships require less maintenance or thrive with a more spontaneous approach.
  • The belief that relationships should always be “work” could discourage people from seeking or expecting joy, ease, and natural compatibility in their partnerships.
  • Cultural differences exist in how love and ...

Actionables

  • you can set a recurring weekly reminder to write down one small way you actively chose your partner that week, then share it with them to reinforce the idea of love as an ongoing decision and commitment
  • For example, jot down how you supported them during a stressful day or made time for a meaningful conversation, and let them know why you made that choice.
  • a practical way to nurture steady commitment is to create a “relationship resilience jar” where you and your partner each add a note every time you overcome a challenge together, then read a few notes during tough times to remind yourselves of your shared growth
  • This helps you see your progress and reinforces the habit of working through difficulties as a team.
  • you can schedule a monthly “relationship evoluti ...

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Why You Keep Choosing the Wrong Person (And How to Finally Stop) | Faith Jenkins

Avoiding Settling and Maintaining High Standards In Selection

Faith Jenkins and Lewis Howes discuss the importance of patience, self-awareness, and standards when choosing a life partner. Their conversation highlights the benefits of waiting, the dangers of settling, and the crucial role of clarity and self-worth in relationship decisions.

Delayed Marriage Boosts Success Through Self-Knowledge and Reduced Incompatibility

Faith Jenkins waited until she was 42 to get married, despite external questions and pressures during her 20s and 30s. She emphasizes that the right timing for marriage is unique for everyone, and for her, waiting allowed for significant personal growth and clarity. Jenkins and Howes note that research shows divorce rates are significantly lower for those who marry in their late 30s or 40s. Howes reflects that if he had married anyone from his previous relationships, he would have certainly divorced, recognizing that the intervening years taught him about his true needs and wants in a partner.

The years prior to marriage allow individuals to experience rejection, heartbreak, and a variety of relationships, building insight into what works and what doesn’t, and helping to distinguish between fleeting desires and genuine needs. Jenkins navigated external pressures and the stigma of being single, using the time to learn, grow, and prepare for a marriage that would bring her lasting happiness.

Choosing a Partner Is a Consequential Decision That Deserves More Deliberation

Both Jenkins and Howes stress that choosing a partner is among the most consequential decisions of one’s life. Marriage affects daily routines, shapes the experiences one has—from 10,000 meals together to world travels—and has a profound influence on children’s worldviews if a couple chooses to have them. Jenkins urges careful evaluation of how a partner’s life intersects with one’s own and warns against rushing into marriage due to pressure, loneliness, or a desire to justify time already invested in a relationship.

Many people feel compelled to continue with relationships they’re not satisfied with, simply because they’ve spent years together or have become close to a partner’s family, but Jenkins emphasizes that true satisfaction and happiness come from choosing well, not out of obligation or external pressure.

Settling Often Stems From Loneliness, Fomo, Low Self-Worth, or External Timeline Pressure

Settling often arises from loneliness, fear of missing out (FOMO), low self-worth, or feeling pressured by external expectations and timelines. Jenkins discusses the subtle shame that can develop from prolonged singleness, especially when others treat it as a personal failing. If one begins to believe that being single is a deficiency, it becomes easy to accept partners who are incompatible or unkind. Jenkins believes addressing internal wounds and fears—rather than just seeking to “not be single”—is essential for long-term happiness and healthy partnership.

Marriage Doesn't Change Fundamental Character or Values

Jenkins contends that marriage does not change a partner's fundamental nature. Expecting a partner to change after marriage—or marrying someone for their potential rather than their reality—leads to disappointment and resentment. Jenkins reminds that weddings may change a last name or create a public celebration, but they do not fix bad habits. Howes agrees, cautioning against choosing a partner in the hope that they will one day become someone else; rather, you should accept your partner as they are, and expect that “winning the pie-eating contest just means more pie”—you ...

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Avoiding Settling and Maintaining High Standards In Selection

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Counterarguments

  • While marrying later can correlate with lower divorce rates, some research suggests that waiting too long may also reduce the pool of available compatible partners and can introduce challenges related to fertility or blending established lifestyles.
  • Personal growth and self-knowledge can occur within relationships as well as outside of them; some people grow together with their partners rather than needing to be fully formed before marriage.
  • Early marriages can be successful and fulfilling for many people, especially in cultures or communities where early commitment is valued and supported.
  • The emphasis on high standards and non-negotiables may lead some individuals to become overly selective or to dismiss potentially good partners due to minor flaws.
  • Not everyone experiences shame or pressure from being single; some people are content with singlehood or do not view it as a deficiency.
  • The idea that marriage does not change people may overlook the ways in which committed partnerships can inspire positive growth and change in both individuals.
  • Focusing primarily on character and values may underplay the importance of physical attraction, shared interests, or other factors that also contribute to relationshi ...

Actionables

  • You can create a weekly “compatibility check-in” where you and your partner each write down three everyday activities you genuinely enjoy doing together, then compare lists to see where your natural overlap lies and plan more of those moments.
  • A practical way to clarify your non-negotiables is to draft a “relationship boundaries and values” card for yourself, listing your top five must-haves and dealbreakers, and keep it in your wallet or phone to review before making relationship decisions.
  • You can set a r ...

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