Discussion Questions for Samantha Irby: I’m Doing My Best (Life Now)

Listen to the conversation between Kate & Samantha Irby, here. 

1. For many of us, “living our best life now” is an illusion—which is why we need humorists like Samantha Irby to help us see the absurdity in being human. How would you put your own, more humorous, spin on the “living my best life now” line?

2. Samantha was a sensitive, inside kid who liked to listen to singer songwriters and read the Sweet Valley High series. Then, both her parents died at 18—and none of the pressures and desires of being young went away with the grief. How do you grieve when life goes on?

3. Reflecting on her mom’s long struggle with multiple sclerosis, Samantha says what makes her the saddest was there was nothing she could do as a young person to fix it. Big chunks of time were lost to feeling stressed out, overwhelmed, and helpless. What has losing your sense of agency cost you?

4. Both Kate and Samantha share hilariously tragic medical dramas in which they don’t spare themselves. This is, indeed, one of Kate’s favorite things about Samantha: she doesn’t make herself the hero in her own stories. How do you think one develops bravery like this—and what gets in the way?

5. Do you ever feel like you’re too much for everyone else? Kate does and wonders if writing is one of way of being honest without the pain of watching other people’s faces fall. What or where or who do you turn to when you need to tell the truth about what life’s really like?

6. Samantha reads an essay in which she destroys the idea that perfection can be attained in three easy self-care steps. “All I want,” she says after, “is to free people enough to just talk about the real stuff they actually do.” So, real talk, what’s humbling and/or hilarious about your self-care routine?

7. Social media can be a great way to connect without leaving our beds, but it can also be one of our most curated spaces. So, how you do interrogate what’s real? How might you use it, like Samantha, “to keep reminding everyone that we’re all disgusting and ugly and that’s fine”?

8. Samantha wrote an episode for the t.v. show Shrill about a fat babe pool party where the main character gets to witness women enjoying their bodies and be transformed by it. Have you ever witnessed a similar scene of shame free, big group, body love? How did the love transform you?

9. Samantha attributes her ability to revel in life to a tough childhood and ongoing depression. What do you think it is about the struggle that can make savoring life more possible? What helps you to pay attention to the good stuff and take joy where you can find it?

10. “Life has not turned out like you thought it would, but you are not alone, it’s just your humanity showing.” Kate ends the podcast with these words and this invitation: let’s take ourselves off the hook for perfection. What’s one small way you can risk being imperfect today?

Bonus: After listening to this week’s podcast, what part of Kate & Samantha’s conversation resonated with you most? What insight will you carry with you?

Discussion Questions written by author, editor, and facilitator Erin S. Lane.

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