Road Tripping with Jen + Tyler Merritt: On Grief, Midlife, Creativity, and the Unexpected Stories That Save Us

In this special Road Tripping episode, Jen invites her partner, actor/activist/author Tyler Merritt, to join her live after a last-minute schedule pivot. What unfolds is a night of honesty, hilarity, vulnerability, and deep connection.

Jen reads two scenes from Awake—one from the earliest days of shock and grief, and one from the chaotic, hilarious adventure of dating again at midlife. She shares the moment her body finally allowed her to grieve, the unexpected relief that followed, and how storytelling helped rebuild her life from the inside out.

Tyler joins her onstage and opens up about his own journey: discovering creativity as a kid in a sports household, what midlife has taught him, how his rare cancer diagnosis reshaped his priorities, and how their love story began on a night in New York City neither saw coming. He and Jen talk candidly about walking through illness together, finding joy even in hard seasons, and why Awake speaks to all genders—not just women.

This episode is tender, funny, surprising, and deeply human—a reminder that grief can crack us open in ways that eventually let the light back in.

“You’re So Brave”: Tyler Merritt Turns the Tables on Jen in Part 2 of Their Vulnerable Conversation

In Part 2 of this episode, we push even deeper — into the personal, the creative, the brave, and the sometimes scary places we go when we dare to  tell the truth. This time, Tyler Merritt has turned the tables on Jen and he’s asking the questions! 

We talk about what it’s like to be seen, judged, misunderstood — and still choose honesty. We talk about Awake and the vulnerability involved with retelling the painful and unvarnished parts of your story. We talk about fear. And we talk about the joy we’ve found in the middle of it all. So let’s jump back in.

In this second installment:

  • Jen talks about the last time that she felt truly brave and what it felt like to unearth and expose some of the most tender and personal moments of her life in such an honest and examining way
  • Tyler asks Jen who was her best model of kindness at a young age
  • Jen shares the song that is reflecting her current vibe in the world
  • And Tyler asks Jen what she wishes more people understood about her

Whales, Boats, and Vulnerability with Tyler Merritt

Recorded live from the Oregon coast on the final day of MeCamp, this special two-part conversation between Jen and her partner Tyler Merritt is the perfect blend of hilarity, heart, and honesty.

In Part 1, Jen and Tyler share stories from their MeCamp adventures — including a whale-watching excursion that got a little too close for comfort, and a near-death boat ride they’ll never forget. They also reflect on the power of personal storytelling, how vulnerability has shown up in their lives and work, and why telling the truth (even when it’s awkward) can be both healing and hilarious.

Discussing the impact of Tyler’s viral video “Before You Call the Cops” to Jen’s reflections on her upcoming book “Awake,” this conversation reveals the transformative potential of embracing vulnerability. Tune in to discover how opening up about our most personal stories can not only heal us but also inspire others to see themselves in our narratives.

  • Tyler talks about the most awkward moment he’s ever had because he opted to be vulnerable and honest instead of protecting his pride
  • He and Jen discuss the hardest truths they’ve ever had to tell themselves
  • And Tyler goes back into the annals to reveal his most embarrassing moment as a performer on stage

 

February 2025: Tyler Merritt’s This Changes Everything

Cancer is a heavy topic. It’s a hard thing for anyone in the family/support system to talk about. It’s challenging for people on the outside looking in to know what to say. And, no question, it’s an arduous, isolating, and disorienting time for the one living with it. For Tyler Merritt, a favorite around the JHBC community, the cancer journey was/is an opportunity to 

He and Jen sit down to talk about This Changes Everything, the recent book which Tyler penned as a humorous and optimistic love letter to his beautiful life following his recent battle with cancer. Written with the same trademark humor, pop culture and musical theater references, (and a sick companion playlist) that we came love in his first book, I Take My Coffee Black, Tyler laces very candid and vulnerable stories from his highly invasive surgery and cancer treatment with anecdotes like a five-page play written about his appendix, subtitles inspired by Taylor Swift songs, and sometimes completely divergent footnotes about the ten best dogs in fiction, to serve as the connective tissue in his much deeper story of joy and healing. It might sound crazy but it works. 

Things may unravel at the end of this discussion when Jen and Tyler debate whether words/phrases like “lovers” and “making love” have gone out of fashion and we’re sorry. 

Surprised by Love: Jen & Tyler On Where They Started and How It’s Going

It’s time to bring a close to our Dating, Sex, & Relationships series. And what better way to wrap it all than hearing a candid conversation from Jen and her person–Tyler Merritt. If you’ve listened to this series, you might have noticed that Jen has mentioned Tyler–a long time activist and author—a time or two, and that part of the reason for this series was to explore some new territory that Jen has only been exposed to over the last year or so as she tentatively put her toe in the dating waters after the end of her 26 year marriage in 2020.  As we’ve stepped through all the new ways we can meet people, or explored the choice to be single, or looked at how to start over after divorce or loss, we’ve heard the threads of Jen and Tyler’s story in all of this mix. And now, they’re here to give us some insight as to “how it’s going,” with all the joys and challenges every new relationship faces, plus some never before heard conversations about how they came together from completely different places in life including; long time married with kids vs. long time single with no kids, navigating the nuances of being a bi-racial couple and coming from completely different cultural circumstances, balancing their careers while nurturing a budding relationship and the bittersweet reality of dating long-distance. This episode is packed with some “in the moment” musings from both Jen and Tyler and also includes some hilarious takes on how a relationship that started as a new friendship turned into long daily text sessions moving to hours long phone conversations, their “define the relationship” talk, and culminating with a fun bonus segment–the For the Love team’s version of “The Newlywed Game,”–where we see how well Jen and Tyler really know each other (you’ll want to see this on video as well over on Jen’s YouTube). 

Letters from Me Camp Week 2: Me Camp Turns to We Camp with Tyler Merritt in MN

This year’s Me Camp is in full swing, community. We have traveled from Austin to Aspen, and now up, up, up to the Northwoods of Minnesota, where we find ourselves in Grand Marais. Nestled on the shores of Lake Superior, this teeny tiny town was home to Jen for 3 weeks. And she is doing it all. Eating a plethora of fried fish salads, skipping rocks in the bay, potentially trespassing to sit on a picturesque roof and read her book and drink her wine. BONUS: Jen is joined by none other than the man of the moment Tyler Merritt, who discusses his unique state of being in the great white north, and his surprising and ever-so-northeastern encounter with a music-loving octogenarian.