Jay Shetty & Lori Gottlieb ON 7 Answers to Dating Questions

Have you ever found yourself repeating the same negative patterns in relationships? Or struggled to communicate your needs while keeping boundaries intact?

In this On Purpose episode, Jay Shetty is joined by Lori Gottlieb, a psychotherapist and bestselling author, to discuss love, connection, and emotional growth. Known for Maybe You Should Talk to Someone and the Dear Therapists podcast, Gottlieb explores why many step into love with unrealistic expectations shaped by social media and pop culture. She shares the importance of shifting from “idiot compassion” to “wise compassion,” recognizing patterns, and owning our role in relationship dynamics.

Understand Why You Are Single

In his coaching practice, Jay Shetty often hears relationship questions. He wants to know from Gottlieb why some feel left behind if they are still single at 28. The psychotherapist explains that progress is not about age but about doing the inner work to understand past relationship patterns. When you dedicate time to examining your behavior, choices, and roles in previous dynamics, you are one step closer to meaningful relationships. She highlights how important it is to engage in self-reflection and to identify patterns so that you stop attracting the same type over and over again.

Gottlieb explains to Jay Shetty the concept of "idiot compassion," where friends validate feelings without encouraging growth, as opposed to "wise compassion," which offers insights into personal accountability. People are unconsciously drawn to partners resembling unresolved dynamics from their past, such as neglect or unreliability. You can break this cycle once you recognize the patterns and the underlying causes; as you understand your values and relational needs, you will begin to attract stable, emotionally aligned, and healthy partners.

Give It Time

In today’s world, society pressures us around relationship timelines, creating this rush into commitments because of age or fear of limited options. Gottlieb explains to Jay Shetty that you need to slow down and stop chasing the next shiny thing. She suggests understanding relational dynamics and addressing normal issues like communication rather than fleeing at the first sign of difficulty. You need to balance the “head” and “heart” decisions and encourage the listeners to consider therapy or thoughtful exploration rather than hastily labeling relationships wrong.

In her podcast, Gottlieb explores relationship topics more in-depth. She shared with Jay Shetty that even if a relationship doesn’t last forever, it can provide valuable personal growth. Being in a relationship exposes patterns, triggers, and opportunities for deeper understanding that you couldn’t achieve if you were single. Contrary to popular belief and media romanticizing, Gottlieb explains that love is not effortless.

A longitudinal study revealed that individuals’ impressions of relationships evolve often. They recount their initial feelings based on how they currently feel in the relationship.¹ The psychotherapist emphasized that rushing to evaluate a relationship based on fleeting first impressions can cause people to overlook genuine potential. In her opinion, dating apps amplify this issue, encouraging users to dismiss connections prematurely due to an illusion of infinite options.

Moreover, first dates are often inaccurate and based on how you want to be perceived by others. It takes more than a single meeting to discern if you can see yourself in a relationship with someone. Gottlieb advises giving relationships time to develop, as initial nervousness or unmet expectations can mask deeper compatibility. True connection often unfolds gradually, beyond superficial charm or idealized fantasies.

What Is Love?

On first dates, we often focus on how we feel about the other person rather than reflecting on how we feel about ourselves in their presence. Lori Gottlieb told Jay Shetty that self-awareness is paramount; a sign of a healthy dynamic is feeling comfortable and natural rather than nervous or overly impressed.

According to Gottlieb, love is not just an emotion but an active verb; relationships require curiosity and a willingness to communicate needs and emotions rather than assuming love will automatically resolve misunderstandings. It’s not only shared interests that guarantee a good relationship. The psychotherapist explains to Jay Shetty that you need to learn your partner’s "operating instructions"—their emotional needs and reactions—similarly to reading a manual for a new car. Putting in the effort to get to know each other on a deeper level creates the foundation for a fulfilling connection.

Moreover, the psychotherapist emphasizes the importance of curiosity about the context of others' actions rather than jumping to conclusions. Directly misinterpreting undesired behavior as disrespect often overlooks deeper reasons. Therefore, she advises the listeners to view relationships as a shared narrative, where the perspectives of both partners contribute to a fuller understanding. This way, instead of villainizing each other, you treat each other with compassion.

We often expect our partners to read our minds, which leads to disappointment. Lori Gottlieb advocates for clear and direct communication rather than assuming your partner will guess what you need. It is a sign of strength to share your desires, she told Jay Shetty. She believes that partners should address concerns early to ensure compatibility. If you know what you expect from the relationship and regularly work on accommodating each other’s needs, you will prevent future resentment and set the foundation for a strong, lasting, and respectful relationship.

Setting Boundaries

Jay Shetty noted that therapy-related terms like “gaslighting” and “boundaries” are misused on social media, creating a victim-blaming culture. Gottlieb warns that boundaries are commitments you make to yourself, not rigid ultimatums for others. They work well when you enforce them calmly and consistently, as opposed to cutting people off impulsively.

If you want to preserve the relationship, it is crucial to implement your boundaries calmly with a persistent person. The psychotherapist explains to Jay Shetty that maintaining consistency is your responsibility, transforming boundaries into tools for self-respect and healthier relationships. People may continue to break your boundaries, but your focus should be on how you respond and maintain control over your behavior.

Have the Difficult Conversations

Jay Shetty references the movie Cat Person, a satirical take on dating misconceptions, to illustrate how dissecting small actions can result in skewed perceptions. Everyone desires to be loved and accepted, and it is essential to be aware of this when analyzing someone's behavior. While some actions are not justifiable, understanding the context may reveal underlying vulnerabilities.

When it comes to marriage proposals, misunderstandings can arise from poor communication and fear of expressing what you want. Jay Shetty believes it is important to communicate openly with your partner to clarify your expectations. Dramatic gestures or assumptions about your partner's intentions only deepen the misunderstandings between you two.

Lori Gottlieb emphasizes the necessity for transparency and honesty in relationships, from defining commitment to making marriage proposals. If someone struggles to articulate fundamental desires, it indicates a more profound issue concerning their readiness for a lasting partnership. Avoiding these discussions to seem less "needy" or "nagging" can result in resentment and a lack of alignment. You should also refrain from staying silent or leading on your partner because it is unfair and wastes both your time.

However, the fear of rejection often prevents people from expressing their true feelings, amplified by our tendency to overrate emotional triggers. Jay points out that not all issues require confrontation, but misjudging others' priorities can lead to unnecessary conflicts. On the other hand, healthy communication focuses on addressing personal values and discomforts, not every fleeting thought.

Growing Together or Apart?

"Future tripping" is when you prematurely imagine an ideal future with a partner, often leading to disappointment when those expectations are unmet. Jay Shetty explains that effective relationships thrive on rupture and repair, where conflicts are addressed collaboratively. It is important to stay present in the moment and focus on how you and your partner handle current conflicts and disagreements.

Lori Gottlieb highlighted the importance of focusing on current relationship dynamics instead of fantasizing about potential outcomes; how partners handle disagreements and show accountability at the moment is the best indicator of lasting compatibility. Faking behaviors or holding back authenticity prevents genuine connection. Yet, you can build a stable foundation for the future if you create an environment where both partners feel valued and seen.

Openly Addressing Challenges

Jay Shetty and Dori Gottlieb discussed common relationship challenges, especially those involving in-laws and shared duties such as parenting. Partners need to understand how life changes with big decisions - it's easier to get through them if you are open to conversations about responsibilities and expectations to avoid future conflicts.

Often, some of the challenges include in-law issues, often stemming from unresolved couple dynamics. Gottlieb explains to Jay Shetty that partners must prioritize their relationship by standing up for one another, particularly when dealing with demanding parents. If a partner fails to defend their spouse, it creates resentment and weakens the bond. Under these circumstances, it is essential to set clear boundaries lovingly to keep the peace while strengthening familial relationships.

Jay noticed the stress many men experience when caught between their mother and their partner. Deciding between the two most important women can make you feel torn and unhappy. So, Gottlieb suggests addressing these tensions in an attempt to regain peace. It shouldn't be about choosing sides but creating an environment where everyone can engage meaningfully.

Feeling Felt

It is essential to allow emotional expression in a relationship, especially when one partner has difficulties opening up. Jay Shetty compared it to navigating a new environment - you need to exercise vulnerability and patience. Naturally sharing feelings contributes to developing an emotional vocabulary and improves mutual understanding.

The psychotherapist introduced the concept of "feeling felt" - having your emotions genuinely acknowledged and held by someone else. It’s the experience of knowing that what you share is understood rather than minimized or brushed aside. When you sense that another person fully receives your feelings in a caring, compassionate way, it builds trust and encourages deeper openness.

Gottlieb pointed out the damaging impact of disrespect in relationships and the necessity of addressing it promptly. To repair ruptures, she advises communicating, becoming self-aware, and showing flexibility. One way to calm your nervous system and become closer when having these conversations is to hold hands.

More From Jay Shetty

Listen to the entire On Purpose with Jay Shetty podcast episode “Lori Gottlieb ON 7 Answers to Dating Questions You’re Afraid to Ask & How to Break Free from Relationship Timelines” now in the iTunes store or on Spotify. For more inspirational stories and messages like this, check out Jay’s website at jayshetty.me.

¹Cortes, K., Leith, S., & Wilson, A. E. (2018). Relationship satisfaction and the subjective distance of past relational events. Journal of Social and Personal Relationships, 35(8), 1092-1117. https://doi.org/10.1177/0265407517704721