Rewind It Back (Windy City, #5)
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Read between May 20 - May 20, 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.
Morgan Conner
WHY DO I WANT TO CRY
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No shit, she’s referring to diamonds, but I’m trying my best to play dumb because preferred ring style is the last thing I want to talk about on a second date. I’d like to know if she’s a kind person. If she and her mom are close. If she enjoys traveling. Shit, I don’t even know if she has any allergies.  “I’m lactose intolerant.”  Her face morphs into confusion at my sudden change in subject. “What?”
Morgan Conner
oh i love this man this is going to be good lmao
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Are you close with your family?”  “Not particularly.” Are you close with your family, Rio? Why yes, I am. I just got back from three months in Boston, spending quality time with my ma during the off-season. Thank you so much for asking.
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I stand and stretch. “Well, I’m heading out. Just wanted to pop in and say hi. Love you guys.” “Love you, Rio.”  “Did you hear that, Ryan?” I ask from the front door. “Did you hear how easily she said that?” He shakes his head at me. “Never going to happen.” “Never say never, Shay!”
Morgan Conner
i love their banter lmao
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Her brothers are professional athletes, so she’s never once batted an eye at me or my teammates who come over, and I always liked that about her.
Morgan Conner
spin off?
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“Want to come play, Hallie?”  “No,” Luke whines. “She doesn’t know how to.”  I give Rio a smile. “That’s okay. Thanks though.”  His attention goes from me to my brother, then back to me, before he returns to the table, taking his seat once again. “It’s your birthday. What do you want to do?”  “You should go play.”  “Rio, let’s go,” my brother begs from the front door. “You go ahead. I’m going to stay here.” “That’s so dumb. She’s fine.”  “I’ll catch up with you later.”
Morgan Conner
i love baby rio too
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To an outsider, this might seem odd, him having a coffee bar when he doesn’t drink caffeine or having dairy milk in his fridge when he’s lactose intolerant. But the thing is, Rio has always been good to his friends, has always had this innate way of loving and taking care of those important to him. One of his best characteristics is making those around him comfortable and welcomed, so a fully stocked coffee station for friends who are visiting makes perfect sense to me.
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I don’t tell him that I don’t like almond milk. I only ordered it when we were younger because I knew he’d ask for a sip of my latte since he couldn’t handle the amount of caffeine if he ordered his own, and I didn’t want the dairy to bother him.
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“I’m going to do it!” His tipsy grin is way too big. “I’m going to go ask for her number.” “Hey, Rook?”  He looks my way, so stupidly excited. “Yeah?” “Sit the fuck down.” “Yep.”
Morgan Conner
I AM SNORTING
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“Do we have a problem here?” he continues. “Should I call the cops?”  “Oh, get so fucked right now.”
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crosses her bare arms over her chest and, like instinct, I peel off my flannel and hold it out to her. “I don’t want your shirt.” “It’s freezing out. Take it or we’re going right back inside so I can punch Ken Doll straight in the face for calling you Hal.”  She rolls her eyes. “Why are all you men so goddamn dramatic?”  Taking my shirt, she slips her arms through it before cuffing the sleeves enough so that her hands peek through. “There. Happy?”
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I wet my lips, leaning in awfully close. “You sure look good in my shirt for not being mine.”  “Get fucked, DeLuca.”
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I smile as I open the door. “Would love to. You just let me know when and where, Hart.”  She enters the loud bar, throwing a middle finger over her shoulder for me to see. But all it does is make my smile grow because Hallie can pretend to be unaffected by me, by us, by our history, but she’s still wearing my shirt when she gets back to work and looks damn good in it.
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I chuckle. “Well, I was ten years old when I got to choose my number for the first time, and I didn’t know what to choose, so I picked my favorite day. I thought I was so cool picking my birthday. Eighty-three. August third. It’s stuck ever since. Can’t imagine having a different number now.”
Morgan Conner
is his number now her bday?
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“This was a last-minute addition,” she admits quietly. “And what happened that was so important when you heard it?”  I already know the answer, but I want to hear her say it.  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.”  It may be her birthday, but I swear, with that single sentence, she just made all my wishes come true.
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Indy’s smile screams that she’s about to guilt trip me. “Remember how you’re my best friend and you’re in love with my husband and would do anything for him and I’m totally cool with your one-sided man-crush?”  “It’s definitely two-sided,” I scoff, glancing at Ryan. “And I don’t know. He’s starting to lose his appeal.” Ryan chuckles. “We need you to watch the kids, Rio.”  “Did they make you ask because they thought you’d have the best chance at getting me to agree?”
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Have you ever dated while living in Chicago?”  “A few dates here and there. A short-term situationship last year, but I don’t think I ever let myself get invested in anyone because I always knew I’d be moving home eventually.”  “And back home, is there anyone there?”  A tick of a smile begins to lift on her mouth, but she brings her water bottle up to her lips to hide it.  “There is!”
Morgan Conner
this has to be a spin off or i will be cranky.
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“No. No, it’s not like that. I’m just looking forward to getting back home. Cruz got traded to our local NBA team this year, but so did his childhood best friend. So, yeah, I’m looking forward to going home.”  Wren doesn’t make eye contact with me as she says it, but I still see that little sparkle when she brings up Cruz’s friend.  “And this new teammate of his…is this the same teammate that’s going to dinner with you tonight?” She shoots me a look. “If you want to keep talking about my brother’s best friend, I’m going to keep pressing you about our neighbor.” “So that’s a yes. No wonder you ...more
Morgan Conner
Liz baby listen, I demand this book from you.
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She bursts a laugh. “Rio, I’m your girlfriend. Why would I go to prom with someone else?” Wait….what? When I don’t say anything, she lifts her head to look at me.  “Oh my God,” she breathes, jumping off my lap, letting the blanket fall to the floor as she does. “Oh my God! Am I not? I thought it was another one of those unspoken things.”  Both her hands fly to her mouth to cover it, but I can see the panic so clearly in her eyes. “Hallie,” I soothe, circling her forearms to pull her hands away. “I wasn’t sure if you wanted to be, but yeah. Yes. Please. I want you to be my girlfriend. You have ...more
Morgan Conner
my hearrrrttt
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“Nice game tonight, thirty-eight,”
Morgan Conner
I CALLED IT THAT IS HER BIRTHDAY MARCH 8th
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His attention moves back to my mouth, once again asking the question, “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.”  With that declaration, he grips the side of my neck and slams his mouth onto mine.
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Needy is literally my number one personality trait.
Morgan Conner
im snorting because it literally is
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“Hallie,” he says, stopping me before I can make it out the door. “When I first started to try to break into this industry, I didn’t have more than ten dollars to my name. I spent my nights delivering pizza just so I could pay my rent because that’s how badly I wanted all of this.” He sweeps his arms out, as if to say this office, this view, this brand. “You shouldn’t be embarrassed to let people know how hard you’re willing to work to get what you want.”
Morgan Conner
PREACH! what a great freaking boss man.
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“Rio,” I whisper. “I might not be ready for that, but we could have this.”   He laughs sardonically to himself and closes his eyes as if it causes him physical pain to say what he’s about to say. “You know I don’t work that way. I can’t do one without the other.”
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“Goodnight, Rio.” I lean forward and kiss his lips one last time before I turn over, finding my way back to my side. All too soon, there’s a heavy arm wrapping around my waist, hauling me towards him until my back hits his chest.  “Are you out of your mind? Just because I need you to be mine before I fuck you doesn’t mean I don’t want to cuddle.” He tucks one arm under me, allowing me to use his bicep as a pillow, while the other one curls around my middle, his hand slipped under my sweatshirt and his palm pressed against my skin. “But I call little spoon next time.”  Chuckling, I curl myself ...more
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defenseman Rio DeLuca is a healthy scratch. Which is a big surprise because Boston is DeLuca’s hometown, and I know he’s got a whole local fan club here to watch him.”
Morgan Conner
i knew he was going to come to her
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“But your game⁠—” “My job, you mean. I took the day off. I told them I had a family emergency. My agent booked me the first flight out of Boston.”  Family emergency. “This game is too important for you to miss.” “Hallie, I couldn’t care less about that game right now. It’s one of eighty-two.”
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I wasn’t able to work once we moved because of how sick the treatments made me. Thankfully, the trial covered housing and included a caregiver’s stipend, but still, things were tight.
Morgan Conner
i think this is why hallie has debt
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“Because I’m in debt.”  He doesn’t react at all. “And why are you in debt?”  Searching his face, I realize he already knows the answer. That’s why he’s not reacting. No, my dad didn’t tell him because he has no idea about it, but this is Rio. The person who knows me better than anyone, even all these years later.  “I think you already know.”  “Your dad’s cancer trial. The insurance didn’t cover as much as you let him believe.”
Morgan Conner
called it
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Rio shrugs like this is the most casual conversation. “Well, I let him, but yeah.”  “Why would you let him? And why would he do that?”  “I let him because I deserved it for lying to him for so long, and he hit me because he was furious after I told him I was in love with his sister.” My eyes go impossibly wide. For multiple reasons.
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I’m cautious though, because most of me doesn’t want to know the answer. “How long is a long time?” He cradles my jaw, his thumb stroking over my cheekbone, and while his eyes are boring into mine, I look away, hoping I can keep my reaction neutral if I don’t have to see his face when he says it.   “Six years.”  My eyes shoot to his.  “I’ve only ever been with you.”
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So,” she begins excitedly. “What kind of house are you going to buy us?” I chuckle at the change of subject. “What kind of house do you want?” “A big one. With four or five bedrooms that we can fill with kids one day.” I can’t wait for that. I can’t wait to marry her either.
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She shakes her head no. “White walls. Boring. Like a big plain box, so when we get there, I can start renovating it to be ours. I’ll paint every wall exactly how we want them, and I can add all the finishes we decide on together. It’ll be my very first design project, and I’ll make it into our dream home.”  I’m having a hard time holding back my smile as I listen. “Is this house in the city or in the suburbs?”  “It depends on where we end up, I suppose. But ideally, we’d live a short drive from downtown so you can get to work, but in a family area that’s a bit quieter. Like the neighborhood we ...more
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“I think because for six years, I watched your life move into this new, impressive phase. You have all these new people around. I mean, you’re literally famous now.”  “Gross.” “But you are, and sometimes I get nervous that because I’m part of your old life, I won’t fit into the new.”   He’s quiet for a long moment before he says, “But you’re not just a part of my life. You’re the center of it. So, if something isn’t fitting around us, that piece needs to change, not you.” He runs his thumb over my knuckle. “And yes, I’m in a different phase of my career than the last time we were together, but ...more
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He’s really doing what he always dreamed of.  “So,” I begin. “Girlfriend, huh?”  “Oh, I’m sorry. Do you think we should take a couple more decades to get to know each other before I start calling you that?”  “I just didn’t know I was, is all.”  “I assumed this was another one of our unspoken things.” He drapes an arm over my shoulders as we continue walking. “But in case it needs to be said out loud… Yes, Hallie Hart, you are my girlfriend. Though, you should know, there’s a good chance I’ll be changing both that title and that last name one day.”
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“Everyone,” Rio announces, “this is my girlfriend, Hallie. Be nice to her or I’ll literally never talk to you again.” There’s a collective laugh throughout the room before Rio tilts my chin up to him. “See you after.”
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“All of us met our husbands after they were already playing in the pros,” Miller says. “How do you feel, getting to see his career form from the beginning to this point?”  Still focused on him on the ice, I simply say, “Proud.”
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He tries to act completely nonchalant about it, moving food around on his plate. “Well, you and Cheryl have been talking about moving Senior Dogs of Chicago into a bigger building. I found one. I bought it. I want Hallie to design it so there’s more room for people to come visit the dogs, hang out with them, and take them on walks.” She stares at him, dumbfounded.  “What?” he asks, trying to bite back his smile. It’s drastically different from the arrogant version I’ve gotten to know.
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That house on my account is my roommate’s home. Actually, Ryan, you might know her brother. Cruz Wilder.” He pauses with his fork midway to his mouth. “Cruz Wilder?” “Yeah, he plays basketball too.” “I’m sorry, what?” He places his fork back on his plate, turning to Rio. “Your neighbor is Cruz Wilder’s sister?”
Morgan Conner
SPIN OFF SERIES?!!
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Ryan laughs but it’s laced with disbelief. “You’ve lived next to Cruz Wilder’s sister for four years and you’ve never once mentioned it? Those brothers are huge names in their own respective sports. The oldest Wilder is going to be inducted into the NFL Hall of Fame one day, and the youngest brother was the MLB Rookie of the Year a few years back.”   “Wait,” Isaiah cuts in. “Easton Wilder? He’s a beast, and he’s only in his third season in the league. You’re living next to his sister?”  Kennedy’s eyes go wide. “He’s amazing. Every time we play against him, I’m shocked by how good he is ...more
Morgan Conner
spin off spin off spin off
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“You’ve been living next to their sister this whole time and never mentioned it?” Kai shakes his head with a laugh. “And you’ve spent all these years fanboying over Ryan?”  “Well yeah, he’s Ryan fucking Shay.” Rio turns to him. “Don’t worry, honey. Cruz Wilder will never be you.”
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“Of course.” “Don’t worry about all of us,” Stevie adds. “We’re all going to still love you.”  Rio’s attention shifts to Ryan. “Is that true, Ryan?”  The tension dissipates with a laugh from everyone, thanks to Rio’s futile attempts to get the basketball superstar to admit he loves him. Ryan shakes his head. “I have no idea what you’re talking about.”
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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.  He slowly turns over his shoulder to look at me.  I lean my chin on my arm that’s resting on him, a painfully big smile on my mouth. “So, you like really like me, huh?” I tease quietly for only him to hear.  “I think we both know it’s a little deeper than that, even if we’re still pretending it’s one of those unspoken ...more
Morgan Conner
CALLED IT
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“I’m going to sign.” “You are?” I hear Indy ask, but I don’t know how to read the tone. Is she surprised, or is she simply agreeing with him? “But I don’t know how I’m going to tell her.” There’s an edge of panic in Rio’s tone. “How is she supposed to come visit? My mom refuses to even let me talk about Hallie, and I’m supposed to assume they’ll be able to be in the same room?”
Morgan Conner
he means his mom visiting chi but shes going to take it as her visitng boston
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“Let you explain?” I laugh sardonically. “Let you explain what? What kind of explanation could you possibly have for sleeping with my boyfriend’s dad? What the hell are you thinking?” “I know,” she says calmly. “I know.” “How long?” “Hallie.” “How long have you been fucking your best friend’s husband, Mom?”  Her jaw tenses as she rolls the answer over in her mind. “It started last fall, after you left for college.”
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Pressing play, I let the music come through the earbuds. I let her listen for a while. I let her be the one to ask.  She looks up at me. “What happened while you were listening to this song?” I smile at her softly. “This is the song I was listening to when I signed my contract extension with the Chicago Raptors.”  Those hazel eyes go wide as she abruptly sits up. “What?”  I just chuckle at her reaction because I know she heard me.  Turning, she straddles my lap, knees bent on either side of me with a mix of panic and confusion etched on her face. “But…but I heard you. After family dinner, ...more
Morgan Conner
called it
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Those eyes start to gloss over again, and she shakes her head. “I thought there was no way, at first. I noticed the white walls and the four bedrooms. The proximity to the city while still being in a neighborhood, but I thought there was no way you would have remembered that.” “I remember everything about us.”
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“Rio,” Indy calls from across the firepit, sitting on her husband’s lap. “Ryan has something he wants to tell you.”  We all shift our attention his way. “Uh…” he stumbles, and Indy gives him an encouraging nod. “I just wanted you to know that…” He clears his throat. “I love you, man.” My eyes go comically wide while everyone else stays perfectly silent.  I’ve been waiting to hear him say that for years.   “I don’t know, Ryan.” I toss my head from side to side, studying him from across the firepit. “It just didn’t hit the way I always imagined it would.”
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You didn’t think I forgot about Monty did you?! A Windy City Series spin-off is coming March 3, 2026 featuring Emmett (Monty) Montgomery and Reese Remington! PRE-ORDER HERE!
Morgan Conner
STFU