Chapter 3
CHAPTER THREE
Cassidy
“When you come to a fork in the road.… take it.”
Yogi Berra
Missing someone didn’t get easier. The grief didn’t lessen.
You just learned to carry it differently—like a weight you stop fighting because it’s part of you now.
Two months without my dad’s laugh, his corny dad jokes, his texts that never used punctuation, or his habit of showing up at my door with takeout “just because he was in the neighborhood.” We used to have dinner every Tuesday.
He’d talk about the team, about the “magic of the game,” while I half-listened and scrolled on my phone, pretending I wasn’t touched by how much he loved it all.
Turns out, those nights were the best part of my week.
I just didn’t realize it until they were gone.
Not when I switched majors three times, or when I quit my first real job to chase a career that didn’t make sense to anyone but me.
He’d roll his eyes when I said I was building my brand, but he still watched my videos, still told me he was proud.
He didn’t understand what I did, not really, but he showed up anyway with a huge smile and words of encouragement.
He told everyone to follow, to comment or like a video. That was kind of his thing.
He was the reason I got into creating content in the first place.
He loved old movies, and my earliest memories were the two of us watching black and white movies and him laughing.
He was always amazed at the creativity of others and sure, being an influencer wasn’t the same as his favorite directors, but it was the inspiration that got me started.
My dad had this quiet belief that people were doing their best. Even when they weren’t. Especially when they weren’t. I used to think that made him na?ve. Now I think it made him brave and wonderful and damn, I missed him.
Without him, everything felt louder. The silence. The expectations. The pressure to keep it together. There were no late-night calls, no bad jokes, no one to anchor me when life spun too fast. Just me, pretending to have it handled.
Two months without Mathias, too. That hit differently, more like a dull ache I kept forgetting about until someone mentioned him. He’d texted a few times after the funeral, but his messages felt like formality, like he was checking a box. I guess I was too.
I used to think we were connected—both of us chasing something bigger, both driven, ambitious.
But maybe we were just two people running parallel, never actually meeting in the middle.
When he left, I didn’t even fall apart. I just …
adjusted. Slid into the empty space he left behind and filled it with work. Content. Plans.
Maybe what I missed wasn’t him at all. Maybe I just missed being seen. Hence, the dates.
I laughed softly to myself at how fast everything had blown up.
In the week since that first game, my numbers had tripled.
The brand deals, the messages, the constant stream of notifications—it should’ve felt like winning.
Maybe it was. But lately, I wasn’t sure if I was chasing success or just staying busy enough to keep from thinking.
My Nine Dates, Nine Games plan had rules. Each guy had to be in on the bit: a few dance challenges, a mini interview, then the game. Keep it light. Keep it funny. Keep it moving. I told myself it was about connection, but really, it was about distraction.
Jeremy, date number two, was thoughtful and kind. He laughed in all the right places, kissed my cheek, and said he had fun. That was the point—it was supposed to end neatly, no strings, no mess.
But the ballpark was something else. The energy, the smell of popcorn and grass, the hum of a crowd that felt alive in a way I hadn’t in months.
I sat in my dad’s seats for the first time, and it hit me—he’d sat there for years, always saving the second spot for me.
I could almost see him beside me, laughing, calling out stats, elbowing me when the team did something great.
I’d turned down so many of those invites. Too busy. Too tired. Too full of myself to realize he just wanted me there.
Now I was here, smiling for a camera, pretending I was fine while the one person who’d never asked me to be anything else was gone.
The biggest shock, though, was learning Nate O’Brien came to my dad’s funeral.
The guy with the aviators and big shoulders was my dad’s favorite player.
Didn’t love that he saw me at my literal worst, but I brushed it off. Our paths wouldn’t cross again.
My phone buzzed with a text, and I stopped curling my hair.
There was another home game tonight, and Nate was starting.
I double-checked this time to make sure he wasn’t scratched.
I wanted to see him pitch. Just him. It made me feel closer to my dad, even though I got the distinct impression Nate couldn’t stand me.
But my GRWM look was a bandana-tied shirt that showed a lot of my stomach, high-top Chucks, and vintage ripped jean shorts. The only way to wear my hair was down and wavy.
“Get ready with me for date two!” I turned the phone around to start my transition. It was awesome; you did this thing where you showed your pre-makeup and hair look, then swung your arms like a bat to reveal the glam look—but I frowned at the text waiting for me.
Cass: Hey, Nate. This is Cass Calloway. I know this is kind of random, but I wanted to reach out.
Cass: I’m doing this Nine Dates, Nine Games thing, and the response has been wild. My dad talked about you all the time—you were his favorite player—and I thought it might be nice to do something in his memory. Maybe a short video together? Share some stories or advice for new players?
The typing bubble appeared. Then vanished. Then came back again.
Nate: No.
Cass: No to what part?
Nate: All of it. I want no part of this shit idea.
Cass: Which idea would that be?
Nate: Using your dad’s name to chase followers.
Was he fucking kidding me? My skin heated with annoyance at his insinuation and misjudgment.
My heart raced as comebacks formed in my mind.
I wasn’t a speed chess player. Quips and wit weren’t my strong points.
I liked being thoughtful when I replied, which was why my job worked for me. I controlled the pace. The content.
But Nate fucking O’Brien insulted me.
Cass: Excuse me?
Nate: Jackson loved this game. He respected it. Turning his memory into some viral sideshow? He’d hate it.
The words blurred as I stared at the screen. My chest went tight. No, my dad always supported me.
Cass: Wow. You don’t even know me, but sure, let’s go ahead and decide what my dad would or wouldn’t approve of.
Nate: I knew him better than you did.
Cass: Oh, that’s rich. You think catching a few innings with him makes you some authority on who he was? Congratulations, O’Brien—you must feel really special.
Nate: I just think he deserved better than this bullshit you’re doing. Social media star my ass. Its shallow.
Cass: You’re unbelievable. I was trying to do something nice, but you’d rather believe I’m using him for clicks.
Nate: If the shoe fits.
I scowled at my screen, pulse still racing. I thought we’d do something fun together but this was mean.
Nate: Stay out of my games.
Cass: Sure thing, O’Bryant.
I intentionally spelled his name wrong, just to mess with him. Men hated that. They hated it so much. When someone left a horrible or disgusting comment on a video, I’d either block them or delete it immediately—but sometimes, I’d reply with a misspelling of their name. Drove them crazy.
Nate: It’s O’Brien. Jesus.
Cass: Need a tutorial on reading comprehension, O’brYAN?
Nate: You’re insufferable.
Cass: And you’re a jerk.
Nate: Then we agree on something.
I started typing another comeback, but his next message popped up before I could hit send.
Nate: You talk like you knew him. But you didn’t. You never came to a single game. Not once. He sat in those seats year after year, and you never bothered to show up. And now you’re turning that into content? It’s pathetic.
My breath caught somewhere between my ribs. The screen blurred as tears burned the backs of my eyes.
That was the last straw. My thumb shook as I hit block, watching his messages vanish into silence.
I dropped my phone onto the couch and stared at the ceiling, my pulse still hammering. I’d reached out hoping for connection—for a chance to talk about Dad, to find some small piece of him in someone who’d known him—and Nate O’Brien had gutted me with the one truth I already hated myself for.
I told myself it didn’t matter. That he didn’t matter. But the ache in my chest said otherwise.
It wasn’t the first or the last time someone would judge me for being an influencer. That part rolled right off. I had blonde hair, boobs, and a ring light—people loved assuming that meant I was shallow. I’d been underestimated my whole life, and I’d learned to let it bounce.
But Nate’s words dug deeper.
He hadn’t just called my job stupid—he’d called my love for my dad fake. Said the quiet part out loud that I already whispered to myself in the dark. That maybe I hadn’t done enough. That maybe posting and talking about him now was too little, too late.
For once, it wasn’t my career he dismissed. It was me.
Ugh. My eyes watered, and I fanned my hands over them. I’d done enough crying the last few months, and I refused to let an entitled athlete make me feel less. How dare he?
Motivated to be even more extra and more distracting, I finished my look as a wild idea took root. I knew exactly what I was going to do to piss Nate off even more.
“How’d you get us on the field, Cass? This is fucking sick.” Luciano Flores was my date tonight. He was a looker, that was for damn sure, and stood as tall as the players. His mouth hung open as I guided him from the dugout toward the infield.
My wild idea?