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April 15, 2019
How can I achieve internal, not external validation?
What is the best way to overcome anxiety of regret?
Is your wife actually interested in your work?
Should you date someone before you’re in love?
Why are bad habits so easy to pick up?
What do you eat? How do you keep healthy?
How do you reconcile “fuck yes” with not trusting ourselves?
How do I cope with not belonging to my community?
Should you tolerate toxic relationships with family?
February 6, 2019
What is the best way to deal with your demons? / How do you learn to love yourself unconditionally?
Do you think it’s important to specialize in a specific task?
What’s the difference between a manageable shortcoming in a friend/partner and a red flag?
Is it possible to continue to grow without fully forgiving those who have harmed/neglected you?
What should I look for in a therapist?
Why is monogamy your preferred choice?
Does it bother you that we’re living in the Matrix?
November 5, 2018
What recommendations do you have for those with an overly sensitive personality?
What’s a healthy way to cope with averageness?
Should you choose a partner based on logic and reason?
How do you balance self-improvement with self-acceptance?
What is the self-limited beliefs you found most difficult to overcome?
How do you follow through on plans without validation?
What would you put on a giant billboard for thousands to see?
What would you do if you were starting your writing career today?
What do you honestly think about Facebook and other social media?
How much space do you and your wife give each other and are you interested in each other’s work?
September 14, 2018
How and where did you meet your wife? What do we like the most/least about each other?
How do you re-write narratives to get out of the victim mentality?
Do you know any 50+-year-olds who did NOT have kids and don’t regret it?
Are you familiar with Jordan Peterson and if so, what are your opinions on his stances, both social and political?
What are your Top 5 movies and why?
There’s so much I want to pursue in my life, how do I determine the thing I want to pursue?
I always hear “Never give up” as a motivational tool. When should I say “Fuck it” and give up?
How do you know when you should get married?
What does it feel like to have found one’s purpose?
What would you say is the most controversial opinion you hold?
Are you writing another book and if so what is it about?
How have you internally handled being around people with shitty values?
May 31, 2018
How can you gain confidence in yourself?
How to get over jealousy
Can we actually change?
Are promiscuous people ruined for monogamy?
What do you think of dating apps?
Dealing with narcissistic people
Passion vs. Practicality
Dealing with past abuse, bullying, and intimacy
Can we get a reading list?
Is it OK to tell white lies?
How to get better with groups
Do you ever take lazy days?
When ‘fuck yes’ makes you say no too much
What’s your take on familial duty?
How do I deal with injustice?
Breaking a “self-help addiction”
More on honesty
Staying positive dating in your 30s
Do you want children?
February 14, 2018
How to make fulfilling friendships?
How do I know I’m doing/being enough?
How do you know you’re with the right person?
How to switch careers with little/no experience?
Where do you find “the one”?
How the fuck am I supposed to meet a guy?
What is currently blowing your mind?
How do you know when you’re not giving enough fuck
Where’s the line between self-respect/entitlement?
Why people can’t accept women who don’t want kids
October 27, 2017
When the world is a steaming pile of shit
How to stop being a dreamer and start being a doer
How to act without expectation
Essential areas of compatibility in a relationship
What to do when neediness comes back?
Why is turning 30 such a difficult age?
How to make up for lost time as a fuck up
Why are we so fearful of rejection?
What the fuck does it all mean anyway?
How do you balance/prioritize your life?
Are our brains ready for monogamy?
The state of masculinity today
Should we own houses or cars at all?
July 18, 2017
Balancing wanting more with with being content
Have you experienced profound periods of nihilism?
How can you become more comfortable with conflict?
How do we cope in a world that’s changing so fast?
How to know if you’re emotionally stable
What do you think about ethical non-monogamy?
The ethics of pornography, sex clubs, casual sex
What’s the fastest way to beat low self-esteem
How do you separate the gold from the shit?
How to create intention-fulfilled relationships
Abolishing competition in schools
What’s the best way to point out real sexism?
What would you change about humanity if you could?
Thoughts on white privilege in the 21st century
How do you find the place where you belong?
Why do some people stay stuck in their worldviews?
What do think you makes a best-selling book?
Changes you’ve experienced as a bestselling author
Was there any inclination to coast after the book?
August 2, 2016
3 Core Components of a Healthy Relationship
May 11, 2016
Brilliant or Bullshit: MBTI Personality Tests