The clang of the cell door opening rang out, sharp as hell in that cold concrete hallway. Diane stepped out, heart thudding, bed-check roll call—the same damn routine, day in, day out. Her name—it couldn’t come fast enough. Maybe today was the day. “Willshire, Diane. You have an approved letter at the inmate’s window in the mailroom.”

Robyn’s letter. Finally.

Her hands shook when she reached for the envelope, the paper thin but heavy in her grip.

Stamped: APPROVED. Hit like a punch. 

The address stared back:

Inmate: Diane Wilshire - #2456-965.

ALICEVILLE FEDERAL CORRECTIONAL INSTITUTION.

From: Robyn Schultz, Palo Alto, CA. 

Receives 1st Letter

Wednesday, September 13

Dear Mom:

I hope you’re doing okay. I’ve got some big news! Last week, Ryder asked me to marry him. Can you believe it? He’s so sweet, and everyone keeps saying he’s going places—he’s already on track for success, so driven! It feels like the whole world is waiting for me to say yes, and part of me wants to jump in. But... I don’t know, maybe I’m just not ready yet.

I keep thinking about Ethan, my construction worker I met at the coffee shop. There’s something about him that feels so right. He makes me laugh, and be myself around him. No pressure, no pretenses. 

But I have this voice in my head: “Think about your future.” Ryder has so much promise, and part of me thinks I’d be crazy to let that slip away. 

But what if I’m just settling? What if I regret not following my heart? It’s like standing at a crossroads with no signs.

It’s been three years now. I want to know why you drove the car that night? What were you thinking? 

Anyway, I’ll keep you posted on what I decide. Love you always, Your daughter. Robyn.

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Responds to 1st Letter

Thursday, September 14th

Dear Sweetheart:

Your letter lit up my day, but it also got me thinkin real hard about choices. I’m so damn proud of your proposal, that’s huge. And your care about your future.

When you brought up that Ethan fella, my heart squeezed a bit. I remember feelin that same pull once—stuck between what feels safe and what feels right. Easy to get caught up in comfortable. What does your heart want?

Back in high school, I had this best friend who was everything to me—a majorette, always strutting her stuff on the field, all shiny and bright. She fell for the football captain, thought it was the right move. But I knew her heart was somewhere else, and I kept my mouth shut. I thought I was protectin her. I was just been a coward, thinkin it was better to keep quiet than risk our friendship. 

Driving the car? When I know, you’ll know. With all my love, Mom.

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After sealing the letter to Robyn, Diane hesitated, the unspoken thoughts pressing on her. I’ve said what I could... but there’s still so much buried. Her hand hovered above the closed envelope, then drifted toward the worn diary beside her. Before she even realized, her pen had begun spilling out the entry 

1st Diary Entry

Saturday, September 16th

Dear Diary: 

Today, I received a letter from my daughter. She’s hopeful. And confused. It’s hard to see her wrestling with the fears about choices.

She still don’t know. About him. The football captain. About my sister. What they did behind her back. All these years, and I never told her. Kept it buried deep. I can still feel it sitting on my chest—the truth. Should’ve just told her it then. Maybe she wouldn’t have ended up marrying the bastard. Everything could’ve been different.

Now I want to share truth, but it hurts, even if it hurts. Maybe finally let go of the pain. It has been long enough. Time serves all sentences.

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Receives 2nd Letter

Saturday, October 14th

Dear Mom:

I just reread your letter, and it’s really got me thinking. I don’t think I ever realized how messy love can be until now. It’s not just the happy stuff—it’s everything all jumbled together. “Is it still love when it makes you question everything?”

I keep asking myself. Love used to seem simple, like holding hands or just feeling close. But now it’s like…secrets and doubts, maybe even doing things that hurt, just because you care. “Maybe that’s just part of it,” I tell myself, “learning to hold on even when it’s confusing.”

I’m starting to feel a bit pressured, you know? Boy Ryder keeps talking about wedding plans, and while I like him, I’m not sure if I love him the way I should. He says all the right things, but nothing about the way he talks or acts feels like love.

With Ethan, I don’t need the right words—the way he looks at me, the way he’s always there, that’s what love feels like. Ethan—he just gets me. We have so much fun together. I feel free. But I can’t ignore the future—everyone says Ryder’s future is golden.

Wish I could just shut my brain off. You always said think things through, and don’t be like you -- this is me trying, but what if I'm just overthinking? What if I lose something real with Ethan because I’m in a future?

I don’t know. I’m lost about it. Stuck between two worlds, and neither feels quite right. And Mom, I’m waiting—why did you drive the car that night? Love you, Your daughter. Robyn

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Diane picked up her pen after reading the letter, but then put it down. I got to think about this for a while.

Responds 2nd Letter

Sunday, October 22nd

Dear Sweetheart:

Your words hit me hard. Sweetheart, ain’t it always a battle? That tug between what’s sensible and your heart. I know doubting, scared shitless your wrong.

I gotta tell you something I ain’t never said out loud. Not to anyone. Back when we were kids, my best friend—God, she was everything. Majorette, life of the damn school. 

She had a shot at real love. She was dating Mark McCormick. He was everything she needed—passionate, fun, and alive in a way that made her even brighter. But much like your Ethan.

But then she started dating the football captain Bob Bascom —a kid from a rich family, college bound—not a high school dropout like your mother. He told her he loved her. She was the one—and she believed him.

I knew he was cheating on her, because it was with my twin sister. But I didn’t say a word. In my mind, I was doing right by her, keeping quiet. Who was I fooling? It wasn’t about protecting her. It was me—too scared I’d lose her friendship, or worse, get blamed for stirring up trouble. Selfish, that’s what it was.

When she married Bob, my heart shattered. I saw it coming, her trust getting ripped apart. I should’ve said something, told her the truth before it was too late. She could’ve found someone who would hold her heart steady.

The silence I kept? An open wound, never healing. My friend deserved the truth. Secrets rot everything they touch. Don’t let anything between you and Ethan start to fester; secrets ruin everything they touch. Not a day goes by that I don’t wish I’d spoken up. And the car? I still don’t know. But if I ever find an answer, you’ll know.

With all my love, Mom

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2nd Diary Entry

Sunday, October 22nd

Dear Self:

These letters, man. Each one is getting heavier than the last. My daughter...? The same confusion tore me apart. And here I am, damn thing. I still can’t shake it. She’s in college, I’m in prison.

And the car? The judge said she’d give me seven years to figure it out. I’m halfway there and I still don’t know. How can I tell Robyn?

That look—my best friend’s eyes when she found out what her husband did. And what I hid from her—it still cuts deep. Why didn’t you tell me? How could you not tell me? —is what I’d have asked me. Gutless Diane. She lost everything because I didn’t speak up. Protecting her? Set her up for heartbreak. Time ain’t erasing it.

I know what Robyn’s thinking; she’s thinking, “If love’s this confusing, is it even worth it?” Or maybe she’s wondering, “Is it still love if you have to hide?” I’d tell her, I’d say, It’s love alright, but it’ll swallow you whole if you’re not careful. But letters don’t talk back.

Every time she writes about Ryder and Ethan, I wanna scream, “Don’t screw this up! Don’t let secrets bury you!

Pick Ethan, then he’s yours.” These walls eat it up and leave me sittin’ in regret.

It’s not just mine anymore—it’s hers, too, but she doesn’t deserve it. A chain wrapped around both of us, draggin her down. I can’t fix it, but damn, if I could just help her past strugglin to breathe under the weight.

This one hit me hard, another day.

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Receives 3rd Letter

Thursday, November 2nd

Dear Mom:

I’ve been thinking’ a lot about your majorette friend—it got me tangled up, wondering’ about choices and secrets. What do they really mean, anyway?

There’s something I gotta know. When you kept that secret, and you saw her, talked to her -- what were you feeling? Did you ever think about what it’d do to her? And that night you drove the car … I keep wondering what made you do that. What?.

I’m tryin’ to get it, how you dealt with all that—the whole mess. It got me thinking about my stuff. Mistakes.

I miss you, Mom, and I’m trying to learn. Love you, Your daughter

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Responds 3rd Letter

Friday, November 3rd

Dear Sweetheart,

Got your thoughtful letter trying to understand my past. When I think back to those moments, the truth is, I was scared. I thought I was protecting my friend, but I was only protecting myself. I didn’t want to lose my only friendship. I was terrified and that blinded me to see what was right.

In hindsight, I wish I’d had courage. Things would have been different. Your questions are so important, and I hope they help you find clarity in your own decisions.

Your heart is brave, and I have faith in you to choose the right path for you. Just remember, secrets matter, and it’s okay to seek the truth—even if it hurts.

I love you dearly, and I look forward to your next letter. With all my love, Mom.

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3rd Diary Entry

Saturday, November 4th

Dear Diary:

How could I have been so blind? Maybe Robyn can break the cycle. I can’t change my past, but maybe she can learn from it. Not too talky tonight. Time serves all sentences.

It still haunts me, that moment of betrayal. That look—my best friend’s eyes when she found out what her husband did. And what I hid from her—it still cuts deep. Why didn’t you tell me? How could you not tell me? It’s what I’d have asked me. Gutless Diane. She lost everything because I didn’t speak up. Protecting her? Set her up for heartbreak. Time ain’t erasing it.

I still see her as she was that day, baton in hand, bright future ahead. She’d look at me and smile, all trust and warmth. When she came back, broken-hearted, the same eyes burned with that question: “Why didn’t you tell me?”

I know what Robyn’s thinking. She’s thinking, If love’s this confusing, is it even worth it? Or maybe she’s wondering, Is it still love if you have to hide? I’d tell her, I’d say, It’s love, alright, but it’ll swallow you whole if you’re not careful. But letters don’t talk back.

Every time she writes about Ryder and Ethan, I wanna scream, Don’t screw this up! Don’t let secrets bury you! Pick Ethan, then he’s yours. These walls eat it up and leave me sittin’ in regret.

It’s not just mine anymore—it’s hers, too, but she doesn’t deserve it. A chain wrapped around both of us, draggin her down. I can’t fix it, but damn, if I could just help her past strugglin to breathe under the weight.

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Receives 4th Letter

Monday, November 13th

Dear Mom:

I’ve been thinking a lot about what you said in your last letter. It’s hard for me to imagine all those feelings. 

When I think about Ryder and Ethan it’s not just about who to marry anymore; it’s about who I want to be. Your story has me thinking. Love you always, Robyn

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Reponds 4th Letter

Thursday, November 16th

Dear Robyn:

Your words have marked on my heart. The questions you’re asking are some of the hardest.

Damn, that secret is a heavy weight I drag around, Keeping it from my best friend. Thought I was doing her a favor, keeping her safe, but who was I kidding? No one. 

It was fear, plain and simple. Cowardice in a loyalty mask. Every damn day I stayed quiet, I’d add another brick to the wall, one at a time. Didn’t even realize how high it got. 

God, there’s nights I just lay here, starin’ at that damn ceiling. I could have taken it all back. Just once, get it right. But peace? No it ain’t comin’ back. All the folks I hurt -- by my choice.

You’re standin right where I was—same crossroads, same fear gnawin at you, wonderin’ what’s right. Scary as hell, I know. But the fact you’re even thinkin about it -- askin questions is more than I could. 

Secrets? They’re rats. Don’t let that be your story. You know which boy is the right one, and which one promises you only misery in comfort.

The night I drove that car, I was in a haze of poor choices. I knew I shouldn’t have gotten behind the wheel, but the weight of everything felt so heavy, and I wanted to escape it. I made the wrong choice, and it has haunted me ever since.

Honley, you got to get this one right. With all my love, Mom.

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She finished the letter, her heart yanked between hope and regret. No, maybe darker than that. Something twisted, lurking in the shadows. Letting the truth out after all these years—like cuttin’ loose a goddamn anchor. Damn. Yeah, sure. Felt more like rippin out a chunk of herself and tossin’ it into the void. But free? Not a chance. Hell no. Diane opened her diary and started to write.

4th Diary Entry

Friday, November 17th

Dear Self:

Damn, that girl had some guts, askin’ the hard shit like that. Gotta give her props. But it scared the hell outta her too—watchin those wheels turn, seein my decisions. Cause one wrong turn, and she’s gonna end up just like me. Stuck. Buried in the past with no way out. Shit, girl was at a crossroads, just like I was. Christ, I’d give anything to yank her back, keep her from steppin’ into that wrong lane—the one that leads straight to a pile of broken dreams and cold-ass regrets.

But that ain’t how this game works, is it? Naw, my past? A ball‘n chain. 

God, I hope she listens. Maybe my screw-ups can light the way, maybe. I ain’t the one to make her choice—that’s her goddamn road to walk—but shit, secrets keep me down.

They’re nothin but black holes. I know. Like the one I have now. 

I drove because getting caught seemed impossible—but not ready to face that truth, not now—and definitely not for her. Maybe tomorrow. There again another secret. Serving time.

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