In this On Purpose episode, Jay Shetty's guest is Lori Gottlieb, psychotherapist and author of the New York Times bestseller Maybe You Should Talk to Someone.

Moreover, Gottlieb is also the co-host of the Dear Therapist podcast and writes an advice column for The Atlantic.

Lori Gottlieb has developed tools to help people change their lives for the better. This episode's conversation is based on listeners' questions. It aims to help you connect with your true self and become happier and healthier.

Only Friendship

Jay Shetty shares a dilemma that a friend is facing: she wants to cultivate good friendships with men without the pressure of it developing into a relationship. Yet she finds herself often guilted or bullied into considering a more intimate connection. Jay notes how challenging it can be to maintain a boundary when you care about the person, but not in a romantic way.

Gottlieb suggests that expressing one's feelings and boundaries in friendships is vital. If someone argues with another about their emotions, it may indicate that the friendship is not very healthy. Therefore, setting limits early on in a relationship is essential. Gottlieb likens early relationships to wet cement that hardens over time, establishing set patterns.

Nowadays, the trend is to have serious discussions through text rather than face-to-face, which can sometimes make conversations even more difficult. Gottlieb points out that people avoid in-person discussions because they fear they might lose control of their emotions or hear something they are not prepared to handle. However, she insists that in-person conversations are more beneficial and effective.

Gottlieb tells Jay Shetty that she encourages the listeners to break the pattern of texting for serious conversations; one should straightforwardly propose to discuss matters in person to gauge if the other person is willing to participate in a more direct discussion. Jay Shetty adds that shifting to in-person conversations shouldn't be seen as groundbreaking but rather a return to a healthier norm.

Navigating Social Anxiety

Jay Shetty and Gottlieb explore the potential root of social anxiety, suggesting it might stem from negative experiences or messages instilled during childhood. These invisible barriers could prevent individuals from interacting confidently in social scenarios.

Gottlieb highlights the importance of revisiting and possibly rewriting these narratives, encouraging the listeners to gradually step out of their comfort zones, starting with smaller groups and progressively expanding to more extensive settings. Like 'baby steps,' this method might help individuals shed the burden of past narratives and build confidence in social environments.

People tend to favor deeper connections with a smaller group rather than pursuing superficial interactions in a large crowd. The challenge lies in navigating social scenarios without fearing revealing one's true self. Yet the power of curiosity is crucial in alleviating social anxiety. Having a set of genuine questions to initiate conversations is a powerful tool in social settings. It helps in fostering deeper connections and allows for a more comfortable and engaging interaction. This way, you can avoid superficial topics that might invoke pressure and unease and facilitate a healthier, more enjoyable social experience for everyone.

Relationship Expectations

Jay Shetty addressed another question from his listeners - dating someone who seems less focused or driven than they are. Gottlieb explains that you can't pick a partner like ordering from a menu, choosing only the qualities you like. People come with different traits, and you have to accept them as they are. If you try to change them, the relationship is likely to fail. Gottlieb suggests it's essential to understand your absolute deal-breakers, focusing more on the person's character than the career or money they might make.

Many people fear settling because they believe there might be someone out there who has all the qualities they desire. This feeling is intensified by societal pressures, especially as they grow older, as Jay Shetty noticed.

Gottlieb emphasizes the importance of focusing on the essential aspects that make a relationship work, like emotional stability and flexibility. Finding someone you enjoy spending time with is crucial, who also makes you feel safe and secure. She advises the listeners to let go of unrealistic expectations and focus on the substantial, meaningful qualities that will contribute to a lasting, happy relationship.

Getting to Know Each Other

Jay Shetty reflects that people are constantly growing and evolving in relationships and how this continuous growth might cause a lack of emotional regulation and flexibility. He emphasizes that when entering a relationship, you usually meet a "work in progress" version of the person rather than a finished product, which is often concealed initially.

Gottlieb tells Jay Shetty that she has introduced the concept of "the ambassador phase," where people generally portray their best selves in the first three months of a relationship. She points out that during this phase, people often ignore their partners' red flags or actual characteristics and instead project their expectations or desires onto them. Gottlieb advocates for active listening to comprehend the deeper aspects of what the other person is communicating. This includes understanding their backgrounds and how past traumas or unresolved issues may affect the present relationship.

Gottlieb mentions the importance of couples therapy to foster growth in relationships, where individuals are compelled to engage deeply with another person's perspective. She emphasizes the need for willingness from both parties to take responsibility and communicate effectively without fearing their partner's reactions. In couples therapy, partners learn to support each other in healing and growing by recognizing and understanding each other's triggers and finding small, compassionate ways to help each other stay calm.

Furthermore, it is paramount to set and maintain boundaries in relationships. Setting boundaries is not about controlling the other person's actions but determining your reactions to their behavior. Consistent maintenance of these boundaries is vital to prevent the limits from being disregarded in the future.

Boundaries as a Sign of Trust

Jay Shetty and Lori Gottlieb discuss the importance of setting boundaries in relationships. Jay emphasizes that respecting one's limits is vital, as it prevents others from thinking they can break them.

Gottlieb explains that boundaries are not barriers but tools to enhance closeness in relationships. Maintaining a balance where these are neither too tight nor too loose is essential. Gottlieb also advises that setting boundaries should be a gesture of wanting to be closer to the person and avoid discussions or criticisms that might push them away.

Jay Shetty notes that sharing your boundaries with someone shows a deep level of vulnerability and trust, as it often involves revealing what triggers or hurts you. He emphasizes the importance of clear communication while setting boundaries; it should not be merely an announcement but convey the intention of fostering closeness and understanding in the relationship.

Discussing Money

Gottlieb and Jay Shetty discuss the necessity of self-awareness and communication, particularly regarding sensitive topics like money. Gottlieb suggests that sometimes people stay in unsatisfying relationships trying to change their partner, possibly repeating patterns from their past. She emphasizes that a healthier approach is to find someone who already shares your values and interests. Sometimes, the perceived "controlling" person in a relationship might feel they have no space to express their thoughts, creating an unhappy atmosphere.

Jay Shetty believes individuals must examine themselves critically to avoid adopting a superior attitude, which can stifle the other person's input and create resentment. He shares an example of a couple navigating income disparities and the discomfort and pressure it brings, particularly to the partner earning less.

Gottlieb advocates for deep conversations where couples explore the underlying issues and emotions associated with money beyond just budgeting. She points out that discussing personal histories and cultural backgrounds related to money and gender roles can enlighten and help foster understanding and compassion in the relationship.

Uncomfortable Conversations

People often avoid difficult conversations because they fear it might lead to arguments or discomfort. However, Jay Shetty stresses the importance of developing skills to initiate and manage difficult discussions about money and other aspects of life involving family or work settings.

Gottlieb highlights to Jay Shetty the kindness in addressing uncomfortable topics, encouraging the listeners to approach these conversations with an open and curious mindset without imposing their viewpoints. She suggests that before starting such a conversation, you should remind yourself of the other person's humanity. You should approach the dialogue to understand their perspective rather than just conveying your standpoint.

Framing the conversation around understanding each other's emotions and backgrounds can be more fruitful than focusing solely on solving the problem. Gottlieb recommends making these dialogues rather than monologues and suggests a compassionate approach, especially in romantic relationships, such as holding hands, to foster a sense of connection and reduce stress during the conversation.

Am I Settling?

Self-awareness and understanding the influences of culture and family on your perceptions of relationships are paramount. Therefore, Gottlieb recommends that individuals scrutinize whether their opinions are genuinely theirs or influenced by culture or family expectations. It is essential to realize that both partners make compromises in a relationship, and it's not a one-way street.

Lori Gottlieb considers seeking a partner who loves everything about you, including your flaws. She explains to Jay Shetty that the vital aspect in determining if you're not settling is evaluating how you feel when you are with the other person. If you feel safe, understood, and have fun with them, you're not settling, and everything else is insignificant.

Jay Shetty observes that many people are influenced by societal or parental expectations when choosing a partner. He advises listeners to consider various aspects of their lives (physical, financial, mental, emotional, and spiritual) to gauge the give-and-take in the relationship more accurately. Additionally, Gottlieb proposes an exercise where individuals try to view the relationship from their partner's perspective to understand their concessions, fostering a more empathetic viewpoint.

Grey Shades of Life

Jay Shetty read a question from a listener who wants to pursue a dream of becoming a comedian but is scared of the uncertainty that comes with it. Gottlieb advises not to think of it as an all-or-nothing situation. She suggests that it is possible to explore a new passion while still holding onto a stable job until the person is sure about the new path.

Moreover, Jay Shetty recommends a gradual approach to chasing a new dream. He emphasizes the importance of learning and understanding the new field before making a giant leap. Jay advises against making hasty decisions to escape an undesirable situation. Instead, he encourages the listeners to learn from the current situation and build upon it for a successful transition.

Gottlieb adds that one should discern whether the move is towards a goal or just an escape from the current situation. She recommends being cautious to avoid jumping impulsively into something new to prevent an unhappy situation without proper consideration. It is essential to slow down and reflect on the decisions, taking time to understand and learn from the current circumstances before moving on to something new. This way, you avoid repeating the same issues in the new venture or relationship.

Benefits of Journaling

To Gottlieb, journaling is a tool that helps individuals organize their often scattered thoughts, offering a private space where no judgment is passed. It can be a pathway to self-discovery, encouraging people to notice patterns and emotions they might overlook daily. Journaling can be a daily reflection that helps track personal growth and changes over time. Gottlieb also emphasizes that the progress made during therapy sessions should be applied and reflected upon in everyday life to be genuinely beneficial.

Similarly, Jay Shetty highlights that journaling is a tangible means to track mental and emotional growth, much like how physical changes can be measured. He shares that revisiting past journal entries has allowed him to witness his personal development and perspective change over time.

Gottlieb further explains that journaling can effectively illustrate the stages of change people undergo when contemplating and making adjustments in their lives. It promotes self-compassion and personal accountability, serving as a kind friend that assists individuals in navigating through their feelings and decisions. Jay Shetty and Gottlieb advocate for incorporating journaling into daily routines, either in the morning to start the day with clarity or at night to unwind and clear the mind before sleep, ultimately helping in personal growth and mental well-being.

Surviving a Break-up

Jay Shetty and Gottlieb discuss the painful experience of break-ups and their impact on individuals. Jay shares a story from a listener who struggled with a sudden break-up after believing they had a future with their partner. The individual found it difficult to find closure, which many experience during a break-up.

Gottlieb explains that break-ups often involve grief, a loss not just of the present but also of the future one imagined with the person. She emphasizes that people navigate through different stages of grief, including denial, anger, bargaining, and depression. Individuals must allow themselves to feel the suffering instead of downplaying it; friends should understand this.

Gottlieb highlights that the narratives we tell ourselves during this time are essential. It's crucial to avoid destructive reports and realize that incompatibility is sometimes the real issue rather than forcing a change to match the other person's desires. She advises not to carry the hurt into a new relationship and to maintain a balance of hope and caution when entering new relationships, learning, and growing from previous experiences.

More From Jay Shetty

Listen to the entire On Purpose with Jay Shetty podcast episode on “Lori Gottlieb ON How to Set and Keep Better Boundaries & Ways to Know if You Are Settling in Relationships” now in the iTunes store or on Spotify. For more inspirational stories and messages like this, check out Jay’s website at

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