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Cover image for How (Not) to Date Your Brother's Best Friend

How (Not) to Date Your Brother's Best Friend

How (Not) to Share

CHASE

Samantha Hastings was nervous.

Oh, great. Now Chase had officially seen everything.

No.

The burning question on his mind was—why in the world was she working in a grocery store?

Or living in a broken-down building?

The peeling paint, the peculiar smell, and the broken stair rail screamed neglect. Chase had always pictured Samantha as Daddy’s precious little princess. More privileges than her brother Stephen and wishes fulfilled on a silver platter.

As they approached her apartment door, the deteriorating wood and the loose handle couldn’t escape Chase’s attention. Samantha turned to face him, wide-eyed and seemingly trapped between him and the door.

Her every breath strained the fabric of her shirt, her chest looking even more pronounced than before. But hey, it was little Sammy, and he wasn’t checking out little Sammy like that. Just noting the changes. Nothing else.

“Look, this place has character, all right?”

He raised an eyebrow. The girl who used to call a mansion home was now casually deeming this apartment—smaller than any walk-in closet she’d ever had—just “all right”? “Sure.”

For a hobo.

As she swung the door open, Chase braced himself for the unexpected. Yet, what he found inside was far from what he had imagined—a snug and tidy space.

Living the high life wasn’t his thing anymore, and he wasn’t one to preach luxury for everyone. But picturing her adjusting to a regular person’s life? That seemed like a stretch.

Here she was, a young woman navigating the mean streets of the city, someone who’d been shielded from life’s rough edges for the better part of her existence.

Interrupting his thoughts, Samantha leaned in. “I’ve got a roommate, Ellie. We work together, so I’m not living alone.”

Leaning forward, Chase scanned the room, half expecting Ellie to materialize out of thin air. However, the apartment felt strangely empty.

“She’s…she’s out of town for a few days. I promise, I’m not making her up,” Samantha stammered, nervously tugging at her sleeve. “Feel free to check her room if you’re not convinced.”

“I believe you…” Chase mumbled, a twinge of guilt settling in. Taking a closer look at her, noticing the way she avoided his gaze and explained herself, he realized he had been acting like a jerk. “Look, Sam. I wasn’t… I’m just worried about you, okay? I don’t get how you ended up here.”

“I could ask you the same question,” she shot back, her familiar assertiveness making a comeback.

“What do you mean?” Chase inquired, his frown deepening.

She gestured toward him, her eyes widening slightly. “Hello, mechanic dude?”

He furrowed his brow. “Stephen didn’t clue you in?”

Sam pointed to her face. “Does this look like the face of a girl who knows anything?”

Fair point. He had assumed she knew the whole story, or at least enough to make sense of his current situation.

“All right, fair is fair. I’ll spill, and then you can fill me in on what happened to you,” Chase suggested.

“Deal,” Samantha agreed, visibly relaxing as the tension drained from her body.

“Mind if I sit, though? I don’t feel like telling you my life story while standing in your…is this a hallway, or are we straight up in the kitchen?” Chase teased, attempting to inject a bit of levity into the atmosphere.

Why was Stephen so tight-lipped? Why hadn’t he opened up about Sam? And why hadn’t he clued Sam in on his own situation?

“Yes,” she replied, shooting him a pointed glare. Samantha took a step back and motioned toward the couch.

Chase followed her cue, settling at one end of the worn-out couch while she claimed the other.

“I suppose I can skip the ‘dead parents’ part. You’re familiar with that saga,” Chase began, alluding to the tragic loss of his parents a while back. His family had once moved into the same elite social circles as Samantha’s, surrounded by extravagant lifestyles.

“Yeah,” she breathed, her voice barely audible.

“So, I stayed back home. My uncle and aunt got custody of me… But, truthfully, they were here, and I was there—like my parents never left.”

He’d been old enough to have memories of them but young enough to power through. Unfortunately, it wasn’t like he’d spent quality time with his parents. They were constantly at events, shipping him off to boarding schools, and hiring nannies.

Not that he didn’t care for them or they for him, but it was a different kind of love. His mother had always been loaded, but his father, born poor, hit the jackpot marrying her.

Meanwhile, his uncle stuck around here, in the realm of poverty and all that jazz.

But they didn’t talk—they kept their distance.

“I was almost done with school when—my aunt called. She said my uncle was sick…” He glanced to the left, avoiding her gaze. He hated this part of the story—it made him feel like a damn asshole.

He never bothered to check up on them. Chase assumed they were relieved to be rid of the burden. He distanced himself, and the occasional check-in to confirm his existence seemed enough. He had been wrong.

Chase swallowed hard, the lump in his throat refusing to go down. “Look, I… When my parents passed, they didn’t leave as much money as I thought they did…” His hand anxiously clutched at his neck, his gaze shifting away from her attentive eyes.

He felt like a complete idiot. No matter how much he worked, no amount of effort could ease the guilt.

Chase couldn’t bring himself to meet Sam’s eyes—the fear of what he might find in them paralyzed him.

“My aunt and uncle—they didn’t want me to know. They busted their asses for me…for me to maintain my lifestyle.”

His utterly foolish, damn fuckboy lifestyle. Nights out drinking, reckless spending, skipping classes, lavishing girls with expensive dates. He kept up with Stephen and the crew, utterly oblivious to the fact that all the while, they were the ones footing the bill.

“My uncle fell ill, really ill,” he began, his voice catching in his throat. “When I found out—I came back here. I dropped out of school and… I worked at his shop until I was ready to take over…and I’ve been at it ever since.”

There was a whole lot more to the tale. The shame he bore. The tears he shed. Chase had thought his life was one thing, but once the facade shattered…he realized how much time he squandered and how self-centered he had been.

And now…now…Samantha was silent.

She gazed at him, her lips forming a small ‘o’, barely meeting his gaze. He didn’t want to see it—the pity. Chase didn’t deserve pity.

They toiled endlessly, sacrificing everything to sustain a life he now understood he didn’t need. It wasn’t fair.

“W-what did your brother say? Where did he say I went?” Anything to shift the focus.

He had assumed the siblings were close, but he was mistaken. Or maybe Chase simply didn’t matter to Stephen.

Stephen was the only link to his old life he maintained, even now. Their exchanges weren’t as frequent, and distance hindered their visits, but they still talked…

“I’m sorry, Chase—I didn’t—I didn’t know… I can’t even imagine…” She bit her lip. “He— he didn’t say a word.”

Sam hadn’t inquired. Why would she? They knew each other due to unavoidable circumstances. They weren’t friends.

Their lives had taken different paths. They weren’t navigating the same life stage with their age difference. Exactly. Here he was, trying to be…brotherly, he was— he was acting out of concern but…

Chase had overestimated his own importance.

“Right, that makes sense.” No one gave a damn about him once the money dried up. “That’s my schmuck story. What’s yours?”

Sam rubbed her hands over her jean-covered thighs, her head still tucked into her chest. Now, though, she shot him a glance from beneath her lashes.

“I think I need a drink before that,” she declared, springing to her feet. She put some real estate between them, then abruptly stopped and turned her head, looking over her shoulder. “Don’t worry, I’m of legal drinking age now. In case you wanted to add that to the list of things to punish me for.”

Punish her.

He resisted the urge to gulp. Nope.

“Sorry, I guess little sisters are always little to me.” Yeah, good reminder.

The smirk on her face wavered for a beat, but then, it was as if nothing happened. She stuck her tongue out at him and resumed her stride, heading for the kitchen with confident steps.

He observed as she ducked down behind the counter, only to pop up a few seconds later, holding a bottle of wine and a colossal grin. “Thank you, cheap wine,” she muttered through pursed lips.

She settled back onto the couch, working the cap off the bottle. Real classy. Chase almost let out a snarky comment. Almost. Until he witnessed her take the bottle straight to her lips, and he couldn’t help but arch an eyebrow.

“Oh?” she remarked, pulling it away, a smudge of wine left on her chin. “Did you want some too?”

“Driving.”

“Right, because Chase Bennett has never tried the art of drinking and driving before.”

Ouch. Touché.

He thumped his chest dramatically, as if wounded. “This Chase is way more responsible.”

“And does Chase often refer to himself in the third person?”

“It depends on his mood.”

A soft chuckle bubbled up from her lips as she shook her head. “I don’t remember you being like this,” she said, eyeing him while she took another swig from the bottle.

“And I don’t remember you unable to afford a glass or a cup.”

Her lips twisted. “This is just easier,” she explained, her fingers clamping down on the bottle’s neck.

“So, am I in for the tear-jerker, or am I the sole genius in the room?”

She nodded. “I guess Stephen didn’t spill the beans about me either?” Sam questioned, looking straight ahead.

He shook his head. “I figured you were back home.” Chase sighed, slouching into the couch. “In his defense… I didn’t bother to ask.” It felt kind of rude to admit it, but he couldn’t let Stephen take all the blame. Chase didn’t launch the inquisition on Sam…why would he?

“Right.” She sucked in her cheeks before exhaling. “Well, I found out my dear father had plans for me.”

“Plans?”

She took another swig from the bottle before slamming it down on her thighs. “Yeah. A son is a successor. You know what a daughter is?” But she didn’t wait for him to answer. “It’s a way to get power. Want to know how?” Again, he wasn’t given a chance to speak. “By marrying her off to whoever is convenient. Pawn off your daughter, get two cows!”

She couldn’t possibly mean…she wasn’t saying…

But he remembered.

Before Chase left, how many mothers came to him, shoving daughters in his face? Yet, he had always assumed they did so willingly. That the daughters had been interested.

But to think some of them had done it on the orders of their family…it made his stomach churn.

“Welcome to a woman’s world,” she declared, lifting her bottle.

“So, your dad…” he cleared his throat, “he wanted you to marry someone?”

“It wasn’t just that,” she said, glancing down at her lap. “He didn’t—he didn’t give a damn, Chase.”

He observed her pause, her bottom lip teetering on the edge of a quiver, as if she was holding back tears. Yet, there was nothing but venom in her eyes. “I thought one of the boys liked me,” she began, before sinking her teeth into her lip.

Oh no. He’d seen that look before. He’d been the cause of it in the past. He hadn’t intended to—but there were a few years where he was an absolute idiot, thinking consequences didn’t matter.

Then they’d sport this exact expression when they found out he was a piece of shit.

Yup.

But it had never hit him like this before.

Now there was a lump in his throat. Damn.

“But—turns out he was an ass.” She chuckled. “You should have heard the stories. You’re looking at the Hastings pornstar, in the flesh. I mean, my dad told me to get over myself,” she said, finally turning her head to look at him.

She was smiling, but there was no happiness, no joy in the gesture.

That he had never done.

To think someone did that to her… It pissed him off. He wanted to hunt down the little weasel and beat the living daylights out of him.

“Sam… I’m sorry.”

She snickered, tears bubbling in her eyes. “Yeah, so…I left. I left, and I didn’t want anything from him. Otherwise, he’d own me. And I wanted to own myself. So there. I live in a crappy apartment, I have a crappy car, and I have a crappy job. That’s how my life ended up like this, Chase.”

He shouldn’t have asked. “Sam…”

She let her bottle rest against her thigh. Lifting her hand, she interrupted his speech, and he shut up. “I-I made my choices, Chase. You made yours. We had crappy situations, and we did what we could. I… I don’t have to justify why I do what I do. It’s my life.”

She wanted to cry, but she wouldn’t do it in front of him. He acted like he knew a lot about her and as if she couldn’t handle herself, as if he had a say about it.

Turned out she didn’t know him, and he didn’t know her.

“You’re right. I’m sorry.”

“It’s getting late,” she said, her voice wobbling.

Chase wanted to say more, wanted to linger, but—he would honor her boundary. He needed to remember she knew a Chase from a different life, and he knew a different Sam.

He’d been in a similar spot, and he would be considerate.

“I’ll give you a shout when your car’s ready?”

“Yeah, thanks.”

Maybe Chase was wrong. He believed he’d shed all remnants of his old life, but he was mistaken. He still had some work to do.

She wasn’t his responsibility.

Sam was a grown woman.

Continue to the next chapter of How (Not) to Date Your Brother's Best Friend

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