Friendship Breakups and Coworker Crushes with Haley Jakobson

On today's episode I'm joined by writer and fellow internet advice giver, Haley Jakobson. When I teased this episode on insta stories a couple of weeks ago, saying “the guest wrote a book on friendship breakups,” dozens of you guessed it would be Haley, and alas, you were right!!! Haley is the author of OLD ENOUGH, a novel that explores, yes, friendship breakups, but also queerness and bisexuality and being a survivor and growing up and away from who we in the Hello Hayes universe call an OG bestie. As I shared with Haley in our 1hr+ conversation, her depiction of friendship explosions were so vivid and familiar that I felt physically uncomfortable while reading. The novel can be heavy but in the safe and skilled hands of a writer like Haley, I felt held the entire time. OLD ENOUGH has the full weight of a Hello Hayes book recommendation!

Our conversation covers what we’ve learned about ourselves as writers, why friendship break-ups are so painful, a Hello Hayes (and Haley) question about having a crush on a coworker while you’re in a relationship, and so much more. I cry at one point, obviously.

0:00 - Who is Haley Jakobson?

4:20 - Selling her first book

8:00 - Stepping in front of the lens

10:30 - Writing about pain

13:23 - Our love of book "Acknowledgments" sections

14:00 - Earnestness is underrated

15:30 - A hate comment that I still think about

19:00 - Friendship break-ups

19:30 - Vow of celibacy from best friendship

25:18 - What does the patriarchy have to do with it?

32:00 - Why Hayes admires Haley & unexpected tears

35:42 - On not being an "Emily Henry" type of writer

37:00 - The duality of Haley & the creation process

41:45 - The worst question aspiring writers ask

43:00 - What Hayes has learned about herself as a writer

45:30 - "Creative foreplay"

45:00 - Spontaneous vs responsive desire

49:23 - Writing sex scenes

53:00 - Hello Hayes letter

1:05:44 - The story behind the title OLD ENOUGH

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