The Book That Broke My Heart and Filled It Right Back Up
- Jonathan
- Apr 12
- 3 min read
I hadn’t ever read a memoir. My comfort zone is mysteries and thrillers—the kind that keep you guessing until the very end. But Always Kiss Me Goodbye by Jennifer Osler-Bolton landed in my hands because she’s one of my customers. Someone I’ve gotten to know and truly admire for her kindness, warmth, and the light she brings into the world. So when she released a book, I knew I had to support her.
I just didn’t expect it to undo me—in the best way.
From the start, Jennifer is clear: this is a book about her personal relationship with God. As someone who grew up in the church, that immediately gave me pause. Religion is complicated for me. I was outed in high school by a youth pastor, and long before that, I was an eight-year-old boy praying to God to either “fix” me or let me not wake up, because I didn’t understand how being gay could ever be okay. Religion told me it wasn’t. People told me it wasn’t. And eventually, I believed them.
So I was nervous. But I also trust Jenn. She’s trusted me with my candles and with my story—it was my turn to show up for hers. And I’m so glad I did. Because what I found in her story wasn’t judgment or exclusion. It was raw. It was love. It was faith—heavy, real, and deeply personal. The kind that doesn’t try to control, but instead chooses compassion.
Her story begins with love—two high school sweethearts building a life, creating a family, and navigating the world together. But it shifts into grief when her husband, Ryan, tragically passes away. I cried through the first hundred pages. Not a quiet cry—a real, guttural ache. Puffy eyes, splotchy face cry. And yet, I couldn’t stop reading.
Jenn’s writing is intimate, like you’re a camera floating just over her shoulder as she navigates the days, weeks, months, and years after her world changed forever. You feel her heartbreak, her isolation, her strength. And when the man in the red jacket enters her life later in the book, I cried again. This time, they were tears of joy. The butterflies she felt, her hesitation to speak to him like a schoolyard girl, even as a grown woman counting to three before approaching him… the love tragedy turned love story—it was so real, and so beautiful.
What makes this story truly remarkable, though, is the way Jenn holds on to her full devotion to God—even as her own church begins to question, shame, and ultimately push her away. She shares moments that many wouldn’t dare say out loud—the expectation to conform, the shame disguised as concern, the judgment for loving someone outside their doctrine. The people who once encouraged her walk in faith became the same people who tried to strip her of it the moment she stepped outside their mold.
“It Feels Like the Only Way They’ll Trust My Faith Is If They Control It”
And she didn’t back down. She chose love. She chose herself. She chose truth.
“The Church Wants My Obedience—But I’m Obedient to God First”
She parallels her journey with a book in the Bible, and the way it comes full circle is just… brilliant. I won’t spoil it for you, but it gave me chills. Whether intentional or divine coincidence, the symbolism is unforgettable.
What moved me most, though, is how Jenn continues to show love—to people like me. As a gay married man, I’ve often felt unwelcome in faith-based spaces. But Jenn? She’s never once made me feel that way. Her book didn’t restore my faith in "church"—but it did something more personal. It reminded me that people like Jenn exist. People who believe in God, and in kindness, and in me. That matters more than I can say.
If you’ve ever loved deeply, lost painfully, or questioned where you stand with faith—this book is for you. It’s not preachy. It’s not sugarcoated. It’s real. It made me feel welcome in a space I had felt unwelcome in for a long time—and that made my heart full.
I’ll never forget it.
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