Friend Talk: How to Start Uncomfortable Conversations Within Your Friend Group

Published June 12, 2020 by Sheila Anne Murray

Why are uncomfortable conversations so dang hard to start?

The real treat of a friendship is what happens when you move past feel-good fun and dip into the uncomfortable conversations — the ones that pull at your heart strings, can feel messy as hell, stretch your perspectives, and leave you feeling stronger and more connected.

It isn’t easy to get started. You may or may not feel comfortable talking with your friends about classically vulnerable things such as your vices, sex life, and finances - but have you breached topics such as racism, grief, depression, or socio-economic health disparities?

If you’ve always avoided uncomfortable conversations around challenging topics, ask yourself why. What is it that is keeping you from speaking up? What might you be afraid of? Perhaps you fear it will be awkward, or that you’ll say the wrong thing. Perhaps you fear you’ll be the “buzz kill” friend if you bring up the tough stuff. How would it feel to release those fears?

Cultivating a safe space for uncomfortable conversations is vital in this moment. We are still in the midst of a pandemic (which has had its own host of challenges & changes) and now the world is watching as the US faces the deeply seeded beasts of police brutality & white supremacy. If you are a white woman, and conversations with friends have never broached the topic of race, this is your opportunity to start. If this feels uncomfortable, then you’re on the right track… cue the classic quotes you’ve used in the past around your personal struggles (ie. “grow through what you go through”).

If this is resonating with you, rest assured that having uncomfortable conversations isn’t easy for anyone! It certainly hasn’t always been easy for me. That said, I recognize my privilege as a white woman and I know that alongside the solitary education I do at home, it is vital that I speak out and offer my readers tools during this time, instead of taking a back seat and silently hoping we all “figure it out.”

I will offer 3 steps to help you start having uncomfortable conversations. I hope that it helps to elevate your courage to do the inner work and delve into this tough stuff. Though these steps can be integrated into virtually any topic you want to explore with your friends (both old & new), I invite you to consider starting a conversation around the Black Lives Matter movement. If not now, then when?

Alice walker quote, no person is your friend who demands your silence or denies your right to grow

What is your why for starting an uncomfortable conversation?

Before you reach out to your friends, reach inside and consider why you want to have this conversation. For example, you may want to:

  • Learn something new
  • Make a change in your life
  • Take action in your community
  • Create a space for discussion and cultivation of ideas

Not only will this help you to understand yourself, your needs, and your motivation, it will also help you to set up a thoughtful discussion space with your friends. You can keep returning to your why as the conversation progresses with your group to keep the conversation on track and intentional.

Be clear on what kind of space you want to create

What kind of space is going to help you achieve your why?Space for these conversations isn’t limited to an intimate talk with friends, it can happen in a variety of settings and it’s important to choose the right one for your purpose.Consider if you are looking to have a single discussion or if you want to create a container for an ongoing conversation. If you feel you need something more structured and long-term you may want to:

  • Decide on a cadence for meeting about the topic (ie. weekly, bi-weekly, monthly)
  • Start a book club or documentary club around the topic.
  • Create a separate space for the discussion, such as an email thread, texting thread, or group on social media
  • Commit to attending community events/joining groups related to this topic

Alongside that, consider the values you want to uphold in your group. What values are most important to achieving your why? For example you may use the following values as inspiration:

  • Accountability
  • Respect
  • Openness
  • Embracing imperfection
  • Change-making
  • Compassion
  • Honesty

Consider that not all of this is new! You may already have established values within your friend group without realizing it! If you’ve ever followed a nutrition plan with a friend, relied on a gym buddy, or joined a book club, you’ve already gone through the experience of creating a specific lane of your friendship for accountability, change-making, etc.

Open up the conversation, be compassionate to all viewpoints (even the “no thank-you”s), and be kind to yourself through the process

You’ve decided on your why and you know what kind of space you want to create… Now it’s time to start the conversation with your friends. Reach out to your friends using the platform that feels most natural, and start by keeping things personal — by explaining why you want to have a conversation and what you’d like to create / get out of it.

Be open to the fact that some of your friends may not want to engage in the discussion. This is a reflection of their personal comfort zone; don’t let it distract you from your purpose or take away from your friendship. Just because you may be ready to engage in an uncomfortable conversation doesn’t mean that everyone else will be. Find peace with that.

As you begin the conversation keep in mind that the space that you originally envisioned may evolve, and you may evolve too! Isn’t that what it’s all about? You may say the wrong thing, you may uncover things about yourself and past beliefs that you aren’t proud of, you may feel defensive or hurt sometimes. Just remember, your impact is more important than your intent. Let the space and conversation evolve. Let yourself get uncomfortable and do the work. It’s all part of this beautifully messy learning process.

Starting these conversations is not easy but it’s worth it! If you can be bold enough to ask your friends to cultivate this space with you, compassionate enough to let a friend say “no” without holding anything against them, and open enough to consider new points of view, you will be well on your way to growing within your already strong community. The possibilities are endless.


Starting challenging conversations may not be as fun as a blissful day on the lake or night out on the town, but these conversations can be a key piece to developing a deep relationship with yourself and with your friend group.

The process of developing deep relationships & conversions is not separate from the inner work it requires. This is where a coach comes in. I work with free-spirited, driven women who are looking to develop deep self love, self trust, and take aligned action. Schedule a 20 minute free consultation with me, to learn more about my program and the results of those I work with.

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