3 distilld lessons on insecurities, fears, and heartbreak from Nikki Glaser x The School of Greatness (#995)

Here are the distilld lessons (extended) inspired by the School of Greatness episode featuring Nikki Glaser.

3 distilld lessons on insecurities, fears, and heartbreak from Nikki Glaser x The School of Greatness (#995)

Here are the distilld lessons (extended) inspired by the School of Greatness episode featuring Nikki Glaser.


On this episode of The School of Greatness, Lewis Howes talks to Nikki Glaser about insecurities, fears, and heartbreaks. Lewis and Nikki go over their experiences with bullying and how it affected their approach to dating. They also discuss the steps we can take to help us find more success in approaching and attracting people we like.

Read this if…

  • You want to improve your communication skills
  • You get nervous around someone you like
  • You struggle to accept compliments or validation

Guest bio

Nikki Glaser is a stand-up comedian, actress, and former television host. She was the host of the series Not Safe with Nikki Glaser. Her stand-up special “Perfect” aired on Comedy central. “Bangin’”, another stand-up special by Nikki is streaming on Netflix.

the distilld lessons (extended)

Dating is an important part of life. It can be fun and exciting, but it can also be difficult and challenging. When we want to be involved with someone, we can lose our chance with them because of inner doubts. These doubts prevent us from approaching, talking, or being intimate with someone we like. But when we lean into our fears, address our insecurities, and accept that pain is part of the process, we can find more success and fulfillment in seeking relationships.

On this episode of The School of Greatness, Lewis talks to stand-up comedian Nikki Glaser about the insecurities we have, the heartbreaks we avoid, and the great relationships we can have when we learn to face our fears.

Here are the distilld lessons inspired by the “Self-Image, Intimacy, and the Dangers of Comedy” episode of The School of Greatness podcast:

1. Every part of us—even our imperfections—deserve love.

Our imperfections deserve our acceptance. According to Nikki, she faced a lot of issues with beauty growing up. Even if was made aware of her attractiveness, she always struggled with accepting it. She’s aware of her own beauty but she can’t help but focus on her flaws and limitations.

She traces her struggles with self-image when she was bullied for her looks. She recounts the time she asked her male friend for a pencil but was told to just carve one out from a tree with her buck teeth. She dealt with relentless teasing and bullying while her younger sister was constantly being told she was the pretty one.

Nikki’s childhood experiences hurt her self-confidence. Even if she was the prettiest person in the room, she never felt like she was. She’d always have memories of being bullied. She always felt overshadowed by her sister. These overtake any admiration she may have received.  She says that her insecurities have scared her off long-term relationships. Instead, she sought partners only for short-term sexual pleasure.

There are so many Nikkis among us. We often reject the love people have for us because we don’t think we deserve it. This may be the combined result of our experiences and how we view ourselves. We may never feel attractive, engaging, or smart enough for someone even if we actually are. We’re always seeking validation and there’s never enough of it. We’re stuck in those times when we were rejected or bullied for our flaws and deficiencies. These are our personal traumas that have scarred and prevent us from pursuing meaningful relationships.

Personal insecurities can ruin relationships. When one or both partners enter a relationship without being secure in themselves, they’ll rely on the relationship itself to define their worth. When uncertainty challenges the relationship in any way, individual insecurities get exposed and get in the way of conflict resolution. This can eventually overwhelm one or both of the people in the relationship and lead to a breakup.

We have to realize that we are more than what we lack. Our flaws and shortcomings don’t define who we are as people. We have beauty, potential, and value that only we have. Our unique strengths more than make up for our imperfections.

We can learn to love ourselves despite our flaws. We can focus on the things that make us good people and great partners. In doing this, we can learn to accept the love and appreciation of others.

2. Rejection is part of human connection.

Lewis went through the same struggles with his appearance. He grew up tall, lanky, and with crooked teeth. Because of this, he was teased and ignored by girls. He was once picked last at dodgeball, and considers it a low point in his childhood.

He became fueled by this fear of being ignored and picked last. This helped shape his mentality of being the first one in the gym, and the last one to leave. His efforts bore fruit, and he eventually became a varsity athlete during his high school years. This got him more attention, especially from ladies his age.

There was only one problem: he didn’t know how to talk to women. He spent most of his childhood being ignored, and this fear of rejection stayed with him even as he became popular. To address this, he faced it. Whenever he saw a girl he was nervous to talk to, he talked to them anyway. He did this for three months   every single day. He eventually reached a point where he felt like he could talk to anyone. He still got rejected a lot, but his confidence never faded.

We have to make a move, even if we have cold feet. We won’t always succeed in connecting, but rejection is a part of it. The important thing is trying..

When we’re insensitive to rejection, we can have better relationships. Studies show that being sensitive to rejection might lead individuals to distance themselves from their romantic partners. This reduces opportunities for deeper mutual understanding, and ultimately leads to a lowered relationship satisfaction.

When we accept rejection as a possible outcome of conversation, we can talk more naturally. Our focus now becomes knowing someone instead of getting something out of it. We can show our true selves without worrying too much if they approve of us or not.

3. Nobody is universally liked.

There will be times when people simply won’t take to us very kindly no matter what we do. Nikki has faced this in her relationships, especially in her career as a stand-up comedian. She jokes that she might be one bad joke away from being cancelled. Despite the possibility of being seen as an insensitive, hateful human being by everyone, she maintains her authenticity.

In a magazine interview, Nikki said that a certain college tried to cancel her. The college put out a statement after her show that offered therapy to people who were triggered by Nikki’s jokes. The jokes explored themes of sexual abuse. Nikki wasn’t discouraged by the response. She believes that her act empowers and delights people, and that the experiences she talks about are ones everyone finds relatable.

Being self-confident and authentic has its price, but it’s a price worth paying. We will find ourselves being criticized--or even attacked--for being ourselves. Different people have different personalities, and ours may not fit well with others. When we’re quick to censor ourselves whenever someone reacts negatively, then we’re not letting other people truly know us. We’re essentially trading our personality to please others.

When we accept and stand by our own worth, amidst the rejection and criticism, we can have better relationships with other people. More importantly, these can also lead us to have better relationships with ourselves.

For a shorter conversation, the distilld lessons summary are here.

The School of Greatness

Hosted by Lewis Howes, The School of Greatness features conversations and interviews with the world's best movers and shakers in various industries. The distilld lessons here.

Great! You've successfully subscribed.
Great! Next, complete checkout for full access.
Welcome back! You've successfully signed in.
Success! Your account is fully activated, you now have access to all content.