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How (not) to date your brother's best friend

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Samantha Hastings spent her life in her older brother's shadow. He had it all: good looks, insanely smart, pretty girlfriend, handsome best friend... Tired of being second best, Sam left home to strike it on her own. A string of bad lucks cumulated until one night, her car broke down. The last thing she expected when she walked into the busted mechanic shop down the road was to run into a familiar face she hadn't seen in years. Chase Bennett. Her brother's best friend from high school. Could he make her see that her car wasn't the only thing in need of a tune-up?

Romance / Humor
Megan Blake
4.8 26 reviews
Age Rating:

How (not) to escape



The sound of the screeching voice was enough to raise the hair on her arms. Samantha rolled her lips together, tension forming in her neck. Come on, you got this. She took a deep breath, the expansion of her chest smoothening the wrinkles of her beige work polo.

“Yes, Sarah?”

“What is this?”

Samantha turned her body, stiff like a stick, and cast a glance upon the pile of can goods. She had sweated her life out, piling them up in a pyramid, which was the stupidest design, all because Sarah had requested it.

Now she had a problem with it?

“Hm, the cans of beans you asked me to place?”

Sarah popped her lips, her neon pink lipstick cracking in the folds as she pursed her lips. “Really, Samantha, do you think, this,” she began, pointing at the pile with disdain dripping from her words, “is what I asked for?”

Bitch you asked for a pyramid, and you got a pyramid.

That was the answer Samantha wanted to give her. But couldn’t. Because she needed this job. Like desperately so. If she didn’t, she wouldn’t be able to keep her apartment for long. And she’d already burned her way through a lot of the low-paying jobs when she first arrived…

She couldn’t get fired.

She dug her fingers into her palm, nails scratching at the skin, leaving a trail of red behind. Don’t punch her in the face. Breathe. Breathe. She’s trying to make you lose your shit, don’t let her win.

“You’re right, my bad. I’ll start over.”

Good.” Sarah pushed her shoulders back, her hands resting on her hips as if to feel superior. “When you’re done wasting everybody’s time, go through the dairy products and put the near-expiring stuff at the front.”


“Excuse me?”

Bitch was pushing her luck. Samantha clenched her teeth hard enough to feel her jaw lock. “Yes, I will.”


Sarah turned around, her blue heels clicking, and walked away, leaving Samantha free to stick her tongue out at the back of her head. What a bitch. Sarah had never liked her. There was never a precise reason, but Samantha could guess.

It was because she was a Hastings.

Her family was well off. Very well off. She grew up surrounded by nannies, maids, and whatnot. Up until the day she left her family home, she didn’t know how to boil water. Everything had been done for her.

Not her finest accomplishment.

For a long time, Samantha thought she was happy with that life. If she wanted something, she had it. There was more to it than the money. It was the freedom she thought she had. It wasn’t like she spent Daddy’s money on crazy shopping sprees.

As a child, she had gotten scolded a lot - for running around outside in boyish clothes, for rolling in the mud, or bringing home insects. It wasn’t what a proper lady should do. But she did it anyway.

Maybe it was then that her rebellion had started. Overalls, pigtails, and freedom.

Her mother always let it go more than her father. Eventually, the rules were stricter, but she could try any passion she saw fit. Piano, painting, singing. If she mentioned it, her father would make it happen.

They expected her to graduate, but no one put any pressure on her when it came to grades. She had to be smart, she had to be able to hold a conversation with her father’s social circle but no one was forcing her to become a doctor or get an MBA.

It had felt like she could be anything because no one was expecting her to be something.

And yet that was the problem.

After years of wandering, goal-free, she had begun to think about the future. A career, becoming something, following a dream. The possibilities had been endless. At that moment, her father dropped the truth on her. A husband. Samantha had boyfriends in the past.

Not many.

Sometimes it was hard to trust people. Did they want her for who she was, or because of her father?

Well, her father expected her to be someone’s wife. Someone who would be beneficial to him and his business. All the pieces fell together; they didn’t expect much of her because they only thought of her as someone’s wife.

As if this was 1920…. It wasn’t.

Initially, Samantha had tried. There wasn’t anything wrong with having someone in her life. Yet, none of the boys he introduced her to were good matches. Her father didn’t present her with anyone good to her, or good for her.

It was always someone with a rich daddy.

A disgusting frat boy who’d make lewd comments about her cleavage, he tried to grab her ass or tried to get lay on date number one. Even though the one did. Michael. Sam had been an idiot still, thinking there was a silver lining to it all.

She had fallen for every single line he had thrown her way. Hook, sink, and line. So, she had sex with him after the dinner. Only to find out the next morning, he had bragged to everyone and grossly exaggerate everything that happened.

Based on his story, she would have made porn stars blush.

Samantha had gone to her father, in tears. But did she get help? She did not. Instead, she got a lecture about her behavior. How to be a good woman, and how she should behave when she was with a gentleman.

Her. The one with no worth, no future, nothing. She was the problem according to her father. It was the moment she snapped.

So she rebelled. She tried to attend school, she tried to find a career for herself, but of course - her father dismissed her. He called her irrational, that she was throwing a temper tantrum. Except she wasn’t.

All the freedom she thought she had - wasn’t freedom. It was a different form of control.

So, Samantha sought to prove them wrong.

Which her ridiculous ignorant self thought was an easy thing to do. On a whim, and through tears, she packed a bag, took the money she did have - not from her father, and left home.

Twenty years old, hopeful, and stupid.

She found a town she thought was far enough from home that her name wouldn’t help her and she… made a fool out of herself. Half her money was gone the first week because she had to find a hotel to stay.

She couldn’t afford an apartment.

Oh, and she learned she had no credit to her name, nothing. No guarantor. No job. No higher education. Nothing. When Samantha Hastings was all alone, she was nothing. She went through a couple of roommates before finding someone who could put up with her.

It seemed that she had lacked the proper education regarding responsibilities and sharing of tasks. But she learned. Same with jobs. A gas station, a restaurant… she lost a few before she understood how to do the work.

Now, there she was, three years later.

She had to do community college for almost two years before anyone would even consider her for anything. It had taken every moment of her time, only to still be at the bottom of the barrel.

Since Sam didn’t quite know what she wanted out of life, and her portfolio and resume were quite lacking, she was going for another round of community college. The next semester would begin soon…

Then, her shifts wouldn’t match Sarah’s and all would be well in the world.

Two more fucking weeks.

“Are you stacking that thing again?”

Samantha’s head snapped to the left, watching as Ellie frowned at her tower, the skin between her eyes bunching. Ellie, her savior. The first person to put up with her as a roommate and not kick her to the curb.

She adored her.

Leaving her old life behind also implied losing all of her friends - who had never been her friends in the first place. But it was alright. Because she met some new ones, like Ellie. Despite her under-five-foot stature and her innocent blond bangs, she didn’t take any shit.

Ellie lived her life the way she wanted, and Samantha envied her for that.

“Yeah, Sarah didn’t like it.”

“Sam, how long are you gonna let her bully you like this?”

“Forever?” Samantha replied

Ellie curled her upper lip before closing the distance between them and tugging at her ponytail.


“Stand up for yourself.”

“And lose my job? No, thank you.”

Because of the insane amount of money her family made, she hadn’t been eligible for any grants. A lot of loans. But it was fine. She could do it. She would do it. She hadn’t busted her ass for the past three years to give up now.

“We could find you another job.”

“Ellie, I need the money.”

Ellie sighed, rolling her brown eyes, before dipping her head backward. “Fine. But, please tell me you’re gonna make a scene when you quit.”

“I promise.”

One day.

“Talking about money.”

Oh. Oh.

“What about money?”

Samantha was pretty sure she was up to date on all of her bills. At least she thought so - granted she should probably get her car checked out because that noise was not normal but, hey who had the time or money, right?

“So, I sorta gotta go help out my mom for a few days.”

“She okay?”

Ellie nodded. “Yeah, she has a few appointments for her heart, and… she can’t go by herself. She finally got a spot with a good doc… I found people to cover most of my shifts but…”

One glance and Sam knew. “You can’t close tonight.”

“I can’t close tonight,” Ellie repeated. “But on the plus side, Sarah’s shift is done in two hours and it’ll be you and no one else!”

The advantage of being a small grocery store on a small street. They didn’t need a lot of staff during the evening. Though sometimes, Samantha wasn’t a fan of being all by herself. Not to say the area wasn’t ideal but…

“Yeah, right. Knowing Sarah she will not let me close by myself. She’ll probably say something about me not knowing how to count or whatnot.” Comments she had made before. Because Sam had been so rich, someone counted on her.


“We could not tell her,” Ellie suggested with a sly smile.


Ellie shrugged. “Worst case, she’ll be pissed at me. I’ll tell her something came up.”

Honestly? Samantha loved that option. The thought of spending hours alone with Sarah was enough to make her skin crawl. Plus, taking Ellie’s shifts and having easy hours? It would be a blessing. She needed the money.

“You’ve got yourself a deal missy.”

“Yay! I promise I’ll bring back some of my mom’s cooking.”


There. Sarah didn’t have to ruin her whole mood. Today would be a good day.



There was no missing his name as it flashed across her phone in bright white letters. Her big brother. Unlike her parents… he tried. Though, even saying that he tried was a big word. Unlike her, Stephen remained stuck in her parents’ clutches with no way to freedom.

He was the heir, the golden child, the boy.

All hopes had been pinned on him.

She remembered there was a time when she felt bad for him. He wasn’t allowed to step out of line without any repercussions. He had to have perfect grades, follow the most competitive programs, and be involved in everything.

Stephen never complained, and never said a word out of place.

Now, his behavior wasn’t always flawless. At some point in high school and university, he got into a bit of trouble. He and his best friend Chase had gotten escorted home once or twice… and that wasn’t even including all the girls they brought home.

Of course, since he was older than her, she’d been a kid to them. An annoyance.

Friendships were selective.

His brother wasn’t allowed many friends, but he had been allowed to have Chase. Something about Sam’s mother knowing Chase’s parents… They had passed away when he had been a kid, and his aunt and uncle raised him.

So, his pedigree checked out, and Stephen and Chase became best friends.

Samantha on the other hand had been allowed… girls.

At least until she was eighteen.

So Chase had been the only boy she knew.

Which had led to a little crush back in the day. A tiny one. Very small. It wasn’t like he ever gave her the time of day anyways. Plus, a couple of years before she left home, she had stopped seeing him hanging out of the house.

She’d known him for years but… Stephen was his friend. Not her.

They’d been up to their own things, and moving forward, while she had been left behind. Stephen cared for her but, not enough to face their parents.

When she had walked out, and they had let her, he hadn’t spoken a word. He hadn’t come to her defense, he hadn’t told their father he had been irrational with his demands. No, he had remained a loyal son.

Sometimes, Sam was mad at him. Furious. Other times, she understood. She had been able to walk out - he could not. Why make his own life unnecessarily painful? He couldn’t. It wouldn’t help anyone.

Their father would never change his mind.

But, Stephen did check up on her once in a while. He’d call, he’d text. He had tried to send her money a few times, but she had always refused it. It wouldn’t count if he helped her. At the end of the day, it was their family’s money and she wanted nothing to do with it.

Did she have days where she wanted to run back home, crying, and begging? Yes. Many times. More than she cared to admit. Even after years, it was new to her. The struggles, the pain, the hunger. It had never been her life.

Yet, Sam held on.

She pushed through.

A sigh rattled her body as she clutched her cell phone. She should pick it up. He would harass her if she didn’t. If she gave him some crumbs, he might leave her be. No one knew where and how she lived, it was better this way.

If Stephen saw her apartment, he would lose his damn shit.

Samantha glanced up, confirming no customers were roaming around, and then she picked up the call.


Is that how you greet your loving older brother?”

“Sir Hastings?”

Ha. Ha. Funny girl.”


Great, a customer had walked in.

What was that?”

“Nothing. I’m at work.”

Maybe, possibly, Sam had left out where she worked. Maybe. It wasn’t like being a cashier was shameful in itself but her family had different standards. They expected her to be someone’s pretty trophy wife and working being a cash register wasn’t going to cut it.

Work being?”

None of your beeswax.”

Polite as always.”

“I could have said none of your fucking business.”



He sighed into the phone. “Are you sure you’re alright?

“You ask me the same question every time. My answer is always the same.”

Is this better than home?”

“I don’t know, is it better than being someone’s Stepford wife? I think so.”


“Are we gonna do this again? Look, if you called to know if I’m miserable… I’m not.”

No… that’s not why I called.”

Then out with it, I’m at work. I can’t be on the phone the whole time.”

Dad has been talking about you.”

“Let me guess, he’s been talking about what a disappointment I am. Or maybe, he’s been telling everybody I’m in rehab? Overseas to study? What’s his little story so he can save the family the embarrassment of having me as a daughter?”


Nothing but silence.


There was a squeezing in her stomach, fear flooding her bloodstream. Why wasn’t he replying?

I-I… I don’t know if Dad will let you do your thing forever.”

Sam flicked her tongue against the top of her palate. Control freak. “Sucks to be dad, then. I’m an adult. I don’t need his permission to do anything.”

Samantha… dad… he gets… you know.”

“I know how he gets. That’s why I left. So, sorry to burst his bubble, but I’m never coming back. I’d rather live in the streets.”

I would never let my sister live in the streets.”

“And we both know you’ll never go against Dad, so. Here we are.”

Sammy… I worry about you.”

I’m fine, dummy. Now, bye. Before you cost me my job.”

She hung up, never giving her brother the chance to say anything else. Sam slammed her phone down on the glass counter, her heart racing. She meant what she said; she was an adult, and she could do as she pleased.

They would have to drag her back kicking and screaming.

Except, that was the kind of thing her father could do - if he wished. He would make her life a living hell and force her to come back. Stephen was trying to warn her but… her father had come sniffing around before…

Then he had decided his daughter wasn’t worth it.

Sam lived by one rule; do not make waves. As long as she didn’t attract any attention to herself, as long as she didn’t do anything to harm her father’s reputation… he would leave her alone.

So, though she did as she pleased, she made sure her behavior wasn’t attention-worthy. She kept to herself and she lived the life she wanted. If she kept doing it this way, she should be able to hold on to her life.

Samantha smoothened her bangs, running her fingers until she reached the blue hair tie keeping her ponytail up. Hopefully. She didn’t like that Stephen felt the need to inform her. They barely spoke about their father.


This was probably what her father wanted. He had to know she spoke with Stephen from time to time and the only reason he allowed it was because it kept her connected to the family. He could send messages and receive them.

Her father was all about control.

And Sam was all about paving her own way, no matter the cost.

You can do this. You don’t need him, you don’t need anyone.

One more hour and she would go home, open a bottle of wine and pass out on the couch.

She could do this.

Her day had been sucky enough.

Surely she was due for a break.


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