Rewind It Back (Windy City #5)
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Read between October 24 - October 27, 2025
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Here’s to the 10 characters, 5 couples, 3 teams, 2 sets of siblings, and 1 amazing friend group that changed my life.   This one is dedicated to you, the readers. Thank you for hanging out in Chicago with me.
readwithtrinnn
Stopppp I’m not ready 😩❤️‍🩹
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“Did you just say you raw-dog it when referring to your dairy intake?” “Yeah. If there’s ice cream and I don’t have a pill on me, I’m not going to not eat it, you know?
readwithtrinnn
Rio the man you are 😂💀
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Kennedy: Is this the first Sunday dinner we’re all going to be at since May? Looking forward to seeing everyone.
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NO I LOVE THIS 😭😭🥹
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Miller: He could be hurt or lost or stranded without food and water and we would never know because you won’t ask a simple question, Ryan. Isaiah: I didn’t know the group adopted a puppy.
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Ryan: Fine. Rio, you back or what? Me: Your care and concern for me hold no bounds. Honey, I’m home! Ryan: I hate this. Me: I know. The distance was hard for me too, Ryan. Ryan: I’m leaving this group chat
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My heart flutters like it used to before I remember everything that happened. Because I may have loved Rio DeLuca once, but I don’t anymore.
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“Do you want to be friends?” Well, that was easy. Just last night I was praying for a new friend, and here she is. “Sure!”
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“I pick a song when something cool or important happens so I can remember it. Then when I want to relive a moment, I rewind it back and start the song from the beginning.”
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That thing I’ve been looking for since I moved to Chicago? That connection? That one person some search their entire lives to find? I had already found her when I was twelve years old.
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“Lose him.”
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“Well, maybe that was the first time you were told, but I know for a fact it wasn’t the first time someone liked you.”
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She rolls her eyes. “You can give it a rest, Rio. I get it. You’re going to make sure I’m late.” I’m going to make sure she doesn’t go at all.
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have no idea how to be around you anymore, Hallie.”
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I look back over my shoulder at him. “Good night, friend.” He grimaces. “Yep. Don’t love that.”
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“Hey, Rook?” He looks my way, so stupidly excited. “Yeah?” “Sit the fuck down.”
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“Yeah, well you’re not his, so tell him to keep his hands to himself too.” Her eyes drop to my mouth. “I’m not yours either.” We’ll see.
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“You sure look good in my shirt for not being mine.” “Get fucked, DeLuca.” I smile as I open the door. “Would love to. You just let me know when and where, Hart.”
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I take note of the song that’s playing and keep on driving.
readwithtrinnn
🥹😭
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But frankly, Hallie Hart is all I see.
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She smiles down at me softly. “It was the first time I realized that you may feel the same way about me as I’ve always felt about you.”
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Kai stops at the door, turning back. “Max, you’re the oldest. You’re in charge. Keep an eye on Uncle Rio for us.”
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Me: You’re babysitting? As in you’re the adult in the situation? Rio: Right? Four kids, Hal. This seems dangerous. I need you.
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“It was real,”
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“For me at least. It was real. That’s how I know it exists.”
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“Yeah,” he breathes. “It was real for me too, Hal.”
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“Thank you,” I tell him. “That . . .” “Felt exactly how it’s supposed to,” he finishes.
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“You single, Hal?” I finally give him the long-awaited answer, nodding to tell him yes. “Good.” He takes a slow predatorial step towards me, tone sharp and leaving no room for question. “Because we aren’t fucking friends.”
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Me: Don’t be needy. I have to get my job done. Rio: Needy is literally my number one personality trait.
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Rio: Trust me, Hallie. For the first time in about six years, I’m thinking perfectly clearly.
readwithtrinnn
🥹😂❤️‍🩹
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After all this time, I just wanted my turn.”
readwithtrinnn
Riooo 😭🥺❤️‍🩹
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“You truly have no idea how ingrained you are in here, huh?” He taps his chest. “You’re basically living rent free, Hallie Hart.”
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“Hallie, do you know why I’m not scared?” He holds up the mix CD. “It’s because I know I’ve got a lifetime of getting these from you. We’ve got a lifetime of best moments ahead of us.”
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What is he doing here? But also, can he get to me a little quicker?
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“Even if I didn’t want to see it at first, you guys make a lot of sense together. And she deserves to get what she wants for once, so if she wants you, I hope you stick around this time.”
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I tried to compare every single person I met to you, but there was no comparison.
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And I will spend the rest of my life regretting leaving you behind all those years ago.”
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For years, I’ve taken this fucking boombox everywhere with me. Held on to it, like if I could keep rewinding and replaying these moments we had, then maybe it wasn’t over.”
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“I don’t want it to be over, Hallie.”
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I know that technically, these are your best memories, but they’re mine too. Meeting on that roof, listening to music. Getting the opportunity to fall in love with you is my best memory, and all I can do is hope that one day you’ll let me do it again.”
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“What the hell?” My voice rises. “I hit on every single one of you over the years. And none of you were interested.” Kennedy rolls her eyes. “We don’t count.”
readwithtrinnn
I CANT WITH THIS MAN 😂🤦🏽‍♀️
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“Are you sure that’s not just a first-love thing?” “No, baby. It’s a last-love thing.”
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My heart. His heart, really, when I think about how many times he fixated on my signatures from the mixtapes and CDs I gave him. It’s my favorite part.
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“Why?” “I’m pretty sure you know the answer to that, Hal.” “Tell me anyway.”
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“What are you smirking at?”
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“Just thinking about what a terrible time you had trying to get over me.”
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“Ain’t that the fucking truth.”
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“How people ever thought you were an asshole, I’ll never understand.” Zanders chuckles. “Stevie girl, I hate to break it to you, but you were one of those people.”
readwithtrinnn
My favessss 🥹
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“Okay.” Isaiah holds his hands out to stop her. “He’s not that great, Ken.” “I don’t know,” she teases. “He’s pretty great.” Isaiah takes her left hand and places it flat on the table. “Okay, just making sure it’s still there.”
readwithtrinnn
Still the same crazy energy we know and love 😂😭🫶🏽
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“When I got to training camp in Chicago, they asked me if I wanted to keep eighty-three, but I decided it was time to change it to my actual favorite day.” My birthday. March eighth. Thirty-eight. He’s been wearing my birthdate on his jersey for six years and I had no idea.
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“Every birthday, I used to love listening to you tell me about all your important moments from the year, so I was hoping on this birthday, I could tell you about mine.”
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