In my last blog, I celebrated the start of sweet September by writing about my favorite feel-good scenes. This week, as September winds down, I’m going in a different direction and blogging about my favorite heartbreaking, tearjerking moments. It’s time for sad September!
I’ve always loved sad stories. I find it so cathartic to have a good cry over a tragic tearjerker, and I love creating fiction that inspires the same feeling in other readers. It may sound weird, but I take it as a huge compliment when someone leaves a comment and tells me I made them cry. I don’t often make myself cry while I’m writing (although it does happen once in a while), but when I actually tear up while reading one of my own stories, I know I nailed it. With that being said, here are my top five favorite sad scenes.
5. Kevin’s Grief
My Brother’s Keeper has a lot of depressing moments, but it was difficult to narrow them down to one, mostly because it also includes a lot of comic relief to keep it from being too depressing for too long. But one of my favorite sad scenes is in Chapter 11, which takes place on the day of Kristin’s memorial service. Kevin can’t attend, as he’s still recovering from his injuries in the intensive care unit, which makes the day even harder for him. While everyone else goes to say their goodbyes to Kristin, Kevin grieves alone in a hospital bed, without a sense of closure or the support of his close friends and family. After the service, his mom brings baby Mason to the hospital for a visit. It’s the first time Kevin has seen his son since the accident, which adds a bright spot to an otherwise dark day. But it’s a bittersweet moment, as Kevin realizes how different and difficult it’s going to be for him to raise Mason as a single dad with a severe disability. It’s hard not to feel sorry for him here… but sad moments like these make me happy that I decided to write a sequel to this story, which shows Kevin as a devoted dad who does hard things and thrives despite all the challenges that have been thrown his way. His character has come a long way since this chapter!
4. Nick’s Confession
Chapter 148 of Broken comes during the climax of the story, when Nick learns that his cancer has spread to his lung. His doctor leaves him with a difficult decision to make: undergo a risky operation to surgically remove the tumor that’s dangerously close to his heart, or manage it medically with more chemo and radiation, which might not work to get rid of it. Nick decides to take the risk and consents to surgery. But, before he goes under the knife, he confesses his love to Claire, knowing he might never get another chance to tell her how he really feels about her. It’s a very melodramatic, overwrought scene, especially when you read it while listening to the Evanescence song “My Last Breath,” the lyrics of which were included in the original version of this chapter.
While it may be cheesy, this chapter is a guilty pleasure of mine. It was partly inspired by my favorite movie, Titanic – not so much the actual film, but one specific moment in it. I remember taking a Titanic trivia quiz in one of my teen magazines shortly after the movie came out, and one of the questions was, “How many times do Jack and Rose say ‘I love you?’” I was surprised to learn that the answer was only once. Rose says, “I love you, Jack” toward the end, as they’re floating together in the freezing water. He never says it back, just launches into his last words, telling her not to say her goodbyes, that she’s going to go on and make lots of babies and die an old woman, warm in her bed, not that night. The very intentional use of that single “I love you” stuck with me, and, years later, I used the same technique, saving those words for the end of the story, when Nick knows he might die on the operating table. To me, that made them even more powerful – and made the moment that much more dramatic, yet gratifying. After all these years, this chapter still holds a special place in my heart.
3. Kayleigh’s Death
In Chapter 70 of Song for the Undead, we experience our first fatality among the main group of survivors: Kayleigh. But, first, a bit of back story: Kayleigh was one of the five female original characters my co-writers and I created to balance out the boys. Rose, Dee, and I each came up with a character loosely based on ourselves, and then we developed the last two (Jo and Gabby) together. Gretchen was my character, Riley was Rose’s, and Kayleigh was Dee’s. Relatively early on in the writing of Undead, Rose and I had a falling out with Dee over the kind of issues that tend to arise when you have three young adults trying to write a novel together online: communication, commitment, controlling behavior… Collaborating isn’t easy, y’all! There was fault on both sides, but we’ve since reconciled. The three of us just saw BSB at the Sphere together this summer, so we’re all good now! At the time, though, there was a lot of drama between us. Dee ultimately dropped out of the project, and Rose and I continued writing it without her.
As a result, we decided that Dee’s character, Kayleigh, would be the first casualty out of the main characters. We knew we had to kill at least a couple of them to keep our readers on their toes! But, first, we had to make them care about Kayleigh. This was a challenge, as Rose and I had written her character as a sulky, self-centered, spoiled sorority sister. But, although she’s slower to acclimate to the apocalypse than most of the other characters, Kayleigh eventually comes around and becomes both a valuable member of the group and a more likable character. That makes it all the more tragic when a zombie cracks open her skull and eats her brains! (Tragic… and also graphic, as I had been reading a lot of Stephen King around the time I wrote this chapter and relished in writing descriptions such as “the wormy remains of her brain protruding though the shattered side of her skull.”)
But, in my opinion, the best and most poignant part of this chapter is how Kayleigh’s death affects Brian. Prior to Kayleigh’s death, Brian had lost his faith in God, but as Kayleigh takes her final breaths, he tries to comfort her the only way he knows how: by holding her hand and reciting the Lord’s Prayer. Later, when preparing to perform her funeral service, he picks up a Bible for the first time since throwing his own Bible out the window the night the dead first rose. This is an important moment in Brian’s character’s journey, and that is one reason why I love this chapter.
2. Claire’s Funeral
By My Side is unique in that it has not only an epilogue, but a post-epilogue! What is a post-epilogue, you ask? Well, it’s what you get when an anal-retentive writer is trying to end a really long story on a nice, round number of chapters, like 200… but still has two more chapters to include. So, after Chapter 200, BMS has a sweet epilogue that takes place at Nick and Claire’s wedding and a sad post-epilogue that takes place fifty years later at Claire’s funeral.
The decision to fast-forward five decades to Claire’s (and, later, Nick’s) death in the last chapter was inspired by two other pieces of fiction that I’d read and loved. One was a fanfic, Cover Me With Dreams, which had a huge influence on BMS. The other was an old novel called A Lantern in Her Hand, which is about the life of a pioneer woman. Both stories have beautiful, romantic, tearjerker endings that I clearly tried to emulate in hopes of evoking the same emotional response from my readers that they evoked in me. You can see the CMWD influence in the first half of the chapter, in which Nick and Claire’s family and friends gather to support Nick and say their goodbyes to Claire.
The ALIHH influence comes in the second half, as grieving old man Nick retreats to the solitude of his bedroom to lie down and reflect on the beautiful life and family he and Claire created together. As he drifts off to sleep, he sees Claire standing in the doorway, looking like she did decades earlier. He gets up, forgetting that he’s old and disabled, and she takes his hand, gives it a squeeze, and leads him on to eternity. I’ve always found solace in stories of people who seem to have seen their long-lost loved ones just before dying, and I felt Nick and Claire would be one of those sweet old couples who die within days of one another because they simply can’t go on living without each other. It’s a bittersweet but beautiful ending, and that’s why I had to put this post-epilogue in second place.
1. Nick’s Curtain Call
There was never any question in my mind as to what my number one would be for this week’s blog. Last year, when I was brainstorming ways to celebrate my site’s twenty-fifth anniversary, I thought about doing a countdown of my top twenty-five chapters. I quickly realized I would have a hard time narrowing down twenty-five years of writing (1,772 chapters and counting!) to a mere twenty-five favorite chapters, which is why I decided to do this series of twenty-five top five lists instead. But when thinking about how to rank my “best” pieces of writing and which chapters belonged on that list, I knew Chapter 88 of Curtain Call would probably come out on top. I can’t say it’s my absolute favorite chapter because it’s way too sad, but it is absolutely one of the best chapters I’ve ever written.
Chapter 88 is the last chapter of Curtain Call that’s narrated by Nick. I started writing this story from Cary’s point of view because I already knew Nick was going to die at the end and didn’t see how I could kill a main character in his own first-person point of view. I thought it would be better to have the surviving character be the one to tell the story. But, a few chapters in, I realized that I really wanted to include Nick’s perspective, too, so I started switching off between Cary’s and Nick’s POV. I always assumed that I would write his death scene from Cary’s point of view. But that was before I read the book Before I Die by Jenny Downham, which is written from the perspective of a teenage girl who’s dying of cancer. I read it for inspiration, and it definitely did inspire me to do what I initially thought couldn’t be done and show my main character’s death from his point of view.
While I wrote most of Curtain Call in past tense, I switched to present tense for Nick’s (and, later, Cary’s) last chapter. It starts with him reflecting on his life and his inevitable death, which he knows is not far off. He describes how Cary has tried to prepare him, telling him what to expect, reassuring him that he won’t be alone when it happens, and talking to him even when he’s too tired to respond. Time passes as Nick drifts in and out of consciousness, his condition gradually declining as his friends and family gather to say their goodbyes. In the first half of the chapter, he’s still able to talk back to them and has one last conversation with Howie and AJ. By the second half of the chapter, he can no longer respond, but he listens as Kevin and Brian let him know both how much they love him and how much they will miss him.
I should probably mention that I’m writing this part of the blog with tears trickling down my face at the thought of this ever happening in real life. Like I said in the introduction, I rarely make myself cry while I’m writing because the creative process of putting words on the page tends to take away from the emotional impact of those words. Every once in a while, a certain line will bring a tear to my eye, but I don’t sob over my keyboard as I’m crafting a scene the same way I cry reading sad scenes written by other people. That’s why I always take it as a compliment when someone tells me I made them cry. If a scene packs enough of an emotional punch to bring someone else to tears, then I know my writing was effective. But when a scene I wrote actually makes me cry, I know it’s something special. This chapter is something special. I honestly can’t remember if I actually shed tears while I was writing it, but it’s definitely made me cry the last few times I’ve read it.
I was in my mid-twenties when I wrote Curtain Call, and, at that time in my life, I was lucky enough to have never really lost anyone close to me. In one of my twentieth anniversary blogs, I wrote about how a colleague of mine was diagnosed with stage-four cancer while I was writing this story and how that affected me. Since then, I’ve also lost two grandparents to cancer, so this chapter hits me even harder now.
One of the most poignant parts for me is when Cary reads Charlotte’s Web aloud to Nick to help pass the time and give him something to listen to. It’s a callback to the story of why Cary always wanted a pet pig, so she could be like Fern in Charlotte’s Web, which was her favorite book as a child. Later, we find out the other part of that story, which is that Cary’s mother read her that book to teach her about death as she, herself, was dying of cancer. It comes full circle as Cary reads Charlotte’s last conversation with Wilbur to a dying Nick.
This brings us to the last scene of the chapter, in which Nick wakes to find himself on his tour bus, heading to his next show. “We’re almost there, Nick,” Kevin tells him. “Are you ready?” Nick nods. He’s ready. Before the show, he meets with fans whose lives he’s touched, then gathers backstage with his bandmates for the usual pre-concert prayer circle. Peeking out from behind the curtains, he sees their loved ones in the audience… loved ones who have already passed on. As he climbs onto the platform that will take him up to the stage, he suddenly finds himself alone and feels the first flicker of fear. But as soon as he sees the bright lights over his head, his fear melts away. Of course, the show is a metaphor for the afterlife. I loved the idea of using an actual stage to represent the next stage in Nick’s journey – fitting for a performer. It also fit with his character’s commitment to keep performing for as long as possible, even in the face of an incurable illness.
Fun Fact: I actually wrote the end of this chapter on the wall of my shower with bathtub crayons, which sounds weird, but is something I only do when I’m really inspired, as I tend to be toward the end of a story. I do some of my best thinking in the shower; the ideas seem to flow right along with the water. The words were definitely flowing the day I wrote this scene. Fourteen years later, it’s still one of the best things I’ve ever written.
If you’ve read this far, I’m assuming you also like sad stories, so please feel free to leave a comment and let me know which moments had you reaching for the tissues. I’ll be back next week with a blog celebrating our last Backstreet Birthday Boy of the year!

This last story on your list had me close to tears. Charlotte’s is one of my favorite childhood books as well.
I also love stories that take place over many decades.
Thanks so much for the comment and the compliment! I thought I replied to this the other day, but it must not have posted correctly because I don’t see it. In any case, I love Charlotte’s Web as well! I also enjoy stories that take place over long time periods and involve multiple generations. The book I mentioned, “A Lantern in Her Hand,” was a favorite of my mom’s when she was a teenager. She always talked about how much she loved it, and when I finally read it myself, I understood why. It’s quite a journey! It’s been a long time since I’ve read it, so I don’t remember too many details, but the ending stuck with me.