The beauty of friendships that float in and out of your life

Sitting down with my dear friend (and "You" author) Caroline Kepnes provided a much needed trip down memory lane as we reminisced about life before, during, and after my beautiful Miss Evan

This is the rare Joyful Grief piece that overlaps with my lifestyle platform, The Retaility, which typically has nothing to do with me and, instead, focuses on inspiring women in my orbit. Over the last year, I’ve had friends “in conversation” with one another as part of a series on the site; so, I figured it was only fair that I jump in front of the lens with a friend — before unveiling The Retaility’s next batch of "In Conversation" subjects later this summer. The experience gave me a newfound appreciation for everyone. Because…

Spoiler alert—it turns out sitting down with a friend and discussing private things in a public forum is as bizarre as it is cathartic. Who knew? (You know, other than all of my previous subjects.) But I soon learned firsthand when I sat down with my dear friend Caroline Kepnes, who I met long before life with Miss Evan.

You know those longtime friends who float in and out of your life — and whenever you see one another, it feels like time hasn't passed? (Even if the plot points from year to year prove otherwise.) For me, that person is Caroline.

On top of being someone I’ve known for close to twenty years, Caroline is the New York Times-bestselling author behind the "You" book series, which includes "You" (2014), "Hidden Bodies" (2016), "You Love Me" (2021), and "For You and You Only" (2023). The hit series also led to the Penn Badgley-fronted Netflix show, "You," which aired for five seasons from 2018 to now. Needless to say, she's been busy, and we're almost always overdue for a catch-up.

"It is very strange sitting down and doing this with a friend," I hear myself saying to Caroline at the start of our conversation, which we filmed on an iPhone last year in my Los Angeles backyard.

"It's not the same as sitting down at the bar," Caroline agrees, nervously laughing. "Or at a coffee table."

In the video, we're both clad in neutral sweaters—an unplanned coincidence — with oversized sunglasses that we each repeatedly take on and off as we individually battle our nerves. It's a funny observation to make about oneself, and in truth, I only notice because I'm reviewing this conversation and moment long after it first took place. In theory, interviews and conversations should be a song and dance Caroline and I are used to. Except, once upon a time, she and I were on the other end of it. We asked other people — famous people — questions.

When Caroline and I first met in 2005, she worked for Ted Casablanca's "The Awful Truth," a gossip column for E! Entertainment. Meanwhile, I was writing for InStyle Magazine. Not to date us, but we knew one another when legacy media wasn't referred to as legacy media. It was the only media. This was before Instagram, Facebook, TikTok, and Substack took over. But in a day and age of social media, now everyone is expected to be someone. Some of us want to be more than others.

As writers at heart, neither Caroline, nor myself, have gotten used to being forward-facing — and yet everyone is now expected to be forward-facing. No matter what you do for a living. Hence the on-again/off-again sunglasses. A prop unintentionally intended to mask our individual anxieties and discomfort with perforative conversations that still manage to dig deep.

So. Here we are in my Los Angeles backyard. In nearly identical outfits. Catching up. Our origin stories and experiences diverge from one another, but they eventually intersect when they're meant to. Like the universe and anything else.

In 2018, Caroline's career as an author hit a new level of surreal when "You" debuted on Netflix. Meanwhile, I experienced equally surreal circumstances as my journey took a major detour with the birth of my first child, Miss Evan, who changed my life in every way. As children often do. However, in Miss Evan's case, she was born with a rare mitochondrial disease, which couldn't have been detected prenatally. As a result, my career — for the first time in my life — took a backseat as I navigated unimaginable circumstances, which included stays in and out of the hospitals during Evan's nearly four short years on earth.

During this time, Caroline prolifically wrote and published five books. Concurrently, I stretched myself in new ways as I wrote about life with Miss Evan and the many life-changing lessons she taught me during our time together — and now in the afterlife.

In some ways, Caroline is as connected as she is disconnected to my memory of that era. Caroline, and her hilarious mom, were among the women at Evan's baby shower. Caroline released another novel independent of the "You" series — called "Providence" — in 2018. Just days before I gave birth, I attended an event in Pasadena moderated by Lena Dunham in celebration of Caroline’s book. The week after Evan was born, Caroline’s Netflix television series debuted. I remember bingeing the series between breastfeeding and those initial sleepless nights. Before realizing that life was about to unfold in all the ways every parent fears.

Over the next four years, Caroline was deep in a writing and deadline hole; while I picked up the pieces of my life. We largely lost touch.

But the universe had other plans.

Somehow, Caroline stumbled upon an essay I'd written for the L.A. Times, which is how she learned of Evan's passing. Caroline wrote, "I came across this piece today, one of the most unforgettable, permanently soul-touching things I have ever read, and I am so sorry for your loss. Miss Evan's light is shining through you and I will think of your little star every time I see sunglasses and feel the waves on my toes. My heart is full and the love in your family is profound."

It meant the world. (As every note from every friend, acquaintance, and stranger always does. More on that next week.) Caroline and I reconnected over lunches (as opposed to our old rendezvous at La Poubelle and Birds), and I invited her to be a part of The Retaility's "In Conversation" series, which has featured many longtime (and, sometimes, long-lost friends) like former co-stars Jaime Ray Newman with Lindsay Price, comedian Esther Povitsky with director Kay Cannon, Constance Zimmer with Katie Aselton, and Amanda Kloots with producer Hilary Shor.

I kept pushing the timing of Caroline’s piece because other stories featuring other people somehow seemed more relevant than featuring myself. But revisiting this conversation over a year later feels all the more fitting.

Without any thought or consideration, I recently created "Joyful Grief" (aka this newsletter) to explore many of the same topics and themes Caroline and I discussed last year. Meanwhile, Caroline is celebrating the series finale of "You," a major milestone for any author whose book was turned into a hit series.

I'd love to claim I carefully coordinated the timing of her piece. But the truth is — as a one-woman show at The Retaility, I just hadn’t gotten around to running it.

In some ways, perhaps, it speaks to the odd timing of the universe and how sometimes, I guess, things unfold as they're supposed to. A strange conclusion considering I’ve experienced the unimaginable.

If you want to read the full conversation in which Caroline and I dive into "You," our backgrounds as entertainment journalists, and how we reconnected through the magical Miss Evan, feel free. But somehow that story’s introduction felt fitting for Joyful Grief, too.

Because all roads lead back to Evan. And I hope they always will for the rest of my life until I reach her in the afterlife.