The Gold Digger's Guide to Winning
I’m the gold digger in this story, the woman who uses men to get money, power, and status.
My twin sister, Annie, is the story’s heroine: proud, stubborn, and fiercely independent.
She despises my methods; I mock her naivete.
But when I overheard her deadbeat boyfriend laughing about what a cheap "independent woman" she was, I called her.
“Did you hear that, Annie?” I asked, my voice cold.
“‘Independent woman’ is a trap. It’s a pedestal they put you on so they can enjoy the convenience of not having to provide a thing.”
“If you can use a man to get ahead, that’s a skill. Why wouldn’t you use it?”
She said nothing.
But the next day, I heard she finally kicked her cheapskate boyfriend of five years to the curb.
1
I became aware of my role in this story when I was very young. I knew I was the infamous gold digger, destined to use my beauty to climb a ladder of men, all for the sake of wealth and status.
My sister, Annie Ashton, was the righteous heroine. Taking help from a man was a mark of shame for her; she had to do everything herself.
The moment I understood her character design, I understood my own purpose. The author meant for me to be the foil, the dark reflection meant to prove a point: a woman’s life can only be built by her own two hands, never by relying on a man.
For a fleeting moment, I was disheartened, just a supporting character in someone else’s narrative. But the feeling passed. So I wasn’t the protagonist. It didn’t mean my life had to be worse.
If the author wanted so badly to condemn my choices, then I would show her a different way to live.
And so, armed with my own interpretation of what a "gold digger" could be, I began my life within the pages of this story.
2
The differences between Annie and me were obvious even in kindergarten. At five or six, kids are all about playing and making friends, and the currency of friendship was snacks.
Because we were identical and pretty, boys were always trying to give us candy.
Annie would meet their hopeful eyes with a blank stare and a firm rejection.
I, on the other hand, would always accept with a sweet smile.
Annie never understood. “Anya, you don’t even like sweets. Why do you take them?”
I looked at her and answered seriously. “Annie, they’re giving us snacks because they want to be our friends. They want us to say yes. Besides, their parents gave them those snacks to share. If they don’t give them to us, they’ll just give them to someone else. So why should we be ashamed to accept?”
She turned her head away, a flicker of uncertainty on her face. I knew she loved sweets. I knew she wanted to accept. But she was trapped by the role she’d been assigned, the "independent heroine" label she didn't even know she wore.
“Next time someone offers you something,” I urged her, “just take it. Think of it as a gift to start a friendship.”
Annie hesitated, then gave a small nod.
3
The next day, after school, a little boy approached Annie, his arms overflowing with snacks. He seemed to have gathered all his courage.
“Annie,” he whispered, “these are for you. Will you be my friend?”
I watched from the sidelines, curious to see what she would do. Annie looked from the boy to the mountain of treats in his hands. Her mouth opened as if to say no, but the word wouldn’t come out.
Finally, a decision seemed to form in her eyes. She reached out to take the snacks.
But a sharp voice cut through the air, stopping her cold. “Annie, what are you doing? You can’t just take things from boys!”
We both snapped our heads toward the kindergarten gate. Our parents were standing there, their faces masks of disbelief. They hurried over, pulled Annie away from the boy, and began their interrogation.
“Annie, how could you take snacks from a boy? At best, that’s just being greedy. At worst, it shows a complete lack of self-respect! A girl does not get things to eat by cozying up to boys!”
The little boy, his face burning red, scurried away.
Annie stood there, head bowed, as our parents lectured her. Several times, she glanced at me, her lips moving as if to speak, but she said nothing. She was probably wondering how we could have the same parents, yet I didn’t see this as a shameful act of a girl without self-respect.
4
After that incident, Annie became even more guarded. She refused all help and kindness from boys, determined to prove she could do everything on her own.
In middle school, we were in the same class. Annie’s grades were good, but her chemistry scores were mediocre, keeping her stuck in the middle of the pack. Her deskmate, Peter Vance, was a chemistry whiz and consistently ranked first in our year.
Peter, probably feeling sorry for his deskmate, tried several times to explain the problems she’d gotten wrong. Each time, Annie shut him down.
“Thanks, but I can figure it out myself.”
After a few attempts, Peter gave up.
In a way, Annie was right. In the story, Peter was a total player. Our plotlines were even supposed to intersect. After his crush on my sister went nowhere, he was meant to turn his attention to me, the girl who looked just like her. And I, seeing his good grades and wealthy family, was supposed to fall for him, convinced I’d found a guy with potential. I was supposed to get so wrapped up in the romance that my grades would tank, and I’d end up in a mediocre high school.
But a truly smart gold digger would never let that happen. I would take only what was useful from him and never let him distract me from my goals.
5
When Peter started showing interest in me, I didn’t push him away. Instead, I used his crush to my advantage, bringing him lists of problems I didn’t understand every day. After each tutoring session, I’d thank him with a small snack or a soda.
One afternoon, after I’d packed up my books, he took a sip of his Coke and finally asked the question that had been on his mind.
“Anya, why are you and your sister so different?”
I turned his question back on him. “How are we different?”
He tapped a long finger against his chin, thinking seriously. “She seems to hate relying on anyone. But you… you’re good at using people.”
I smiled as I zipped my backpack. “Peter, ‘using’ is such a harsh word. I prefer ‘leveraging.’ Only the most capable men offer a woman leverage. So, I’m not using you. I’m acknowledging your value.”
Peter had a big ego, and my words stroked it perfectly. He was completely won over.
“You know, Anya,” he said, a grin spreading across his face, “I don’t mind being used by you. But…” His tone shifted. “When are you going to be my girlfriend?”
I dangled a carrot. “When you help me get into Northwood Prep.”
He smirked, full of confidence. “Is that all?”
6
As it turned out, for Peter, it was that simple. With his help, six months later I passed the entrance exam for the most prestigious prep school in the state with the second-highest score in the city.
The first thing I did was block his number and all his social media accounts.
Annie, who had gotten into the same school through her own hard work, was appalled.
“You promised him you’d be his girlfriend if you got in. What do you call this?”
I just shrugged. “How many girls has Peter played with? Is it only okay for a guy to mess with a girl’s feelings, but not for a girl to use a guy to get ahead?”
Annie’s brow furrowed. “Anya, if you keep relying on men to succeed, you’ll regret it one day.”
“I don’t mind,” I said coolly. “The grades I got with his help were real.”
Annie looked at me like I was a lost cause.
Our relationship, while never incredibly close, had been decent enough. But after that, she started to distance herself from me. I understood. She was the story’s independent heroine; of course she’d look down on my methods.
We grew more and more estranged. It reached the point where people were shocked to learn we were sisters.
“Wait, Anya and Annie Ashton are sisters?”
“But they never even talk to each other at school!”
It was true. We didn’t speak at school, and we barely spoke at home.
7
At home, Annie was the sun around which our family revolved, thanks to her innate protagonist halo. I was usually just part of the background scenery.
Like tonight.
Our parents had prepared a feast to celebrate Annie getting first place in her class. That was the only time they’d bring me up.
“Anya, look at your sister. You scored higher than her on the entrance exam, but two years later, she’s at the top of the class. And you? Your grades are slipping. You’re not even in the top fifty anymore.”
Their words didn’t bother me anymore. I knew that even if I were number one, they wouldn’t spare me a single glance that wasn’t meant for Annie. I was just her foil, after all.
Annie, of course, didn’t see it that way. She thought it was all my own doing.
Later that evening, as I was heading to my room, she stopped me. Her expression was calm, tinged with the quiet pride of a winner.
“Do you see now?”
I looked at her, confused. “See what?”
“You can’t rely on other people forever. True security only comes from yourself. You used Peter to help you study and get good grades back then, but what about now? Are you going to rely on him for the rest of your life? If you start studying on your own now, it’s not too late.”
Her self-righteous sermon gave me a headache. Annie, did you really think I could have gotten those scores if I hadn’t been studying my ass off on my own? How dare you dismiss my hard work just because he helped me?
“And you probably don’t know this,” I said, changing the subject, “but I have a boyfriend now. We’re applying to universities abroad together. His family is covering all my expenses.”
Annie froze, her face shifting into a look of profound disappointment. “Anya, there’s no such thing as a free lunch. Everything has a price tag attached.”
I shrugged. “I don’t care.”
8
After that, Annie and I became complete strangers.
Honestly, I never wanted our relationship to get this bad. We weren't in direct competition, and I could understand her protagonist’s pride. Some of her warnings were even born from a genuine concern for me. But we were two extremes in this story, polar opposites, destined to drift apart over our irreconcilable views.
It was a shame, but I knew we could never convince each other. Perhaps being strangers was the best we could do.
As college entrance exams approached, I was a bundle of nerves, juggling exam prep and my study abroad applications. Everyone was in the final sprint.
And that’s when Annie got caught in a relationship.
The boy was Ryan Miller, a broke kid from her class with nothing to his name but a pretty face. The news sent shockwaves through the school administration. Annie was the top student in her year, the school’s only real hope for an Ivy League acceptance. They were terrified the relationship would tank her grades but were equally afraid that handling it badly would affect her performance.
So, they came to me, asking me to talk to her as her sister.
I refused at first. I knew she wouldn’t listen to me.
But Annie’s homeroom teacher told me that Annie often asked about my grades and my class rank. She insisted Annie cared about me, that I was the perfect person for the job.
So, one day after school, I waited for her outside her classroom.
9
When she saw me, a flash of surprise crossed her face before being replaced by her usual calm mask. “What are you doing here?” she asked.
I didn’t beat around the bush. “I heard you have a boyfriend.”
She nodded, unfazed. “So?”
“I just wanted to see what kind of guy would make you risk everything right before the biggest exams of your life. Annie, is he handsome? Is his family rich? What are his grades like?”
My words wiped the calm from her face, replacing it with a look of derision. “His family isn’t rich, and his grades are average. He’s not the type you’d be interested in. But so what? I’m not you. I don’t want anything from him. I believe I can get everything I want on my own, without needing a man.”
Her answer was exactly what I expected. The conversation was a dead end.
But as I turned to leave, I couldn't stop myself from looking back.
“Annie, the biggest mistake you can make with a man is to want nothing from him. It’s okay for you to have everything, but it’s not okay for him to have nothing.”
Her reply was ice-cold. “Thanks for the advice. I don’t need it.”
My twin sister, Annie, is the story’s heroine: proud, stubborn, and fiercely independent.
She despises my methods; I mock her naivete.
But when I overheard her deadbeat boyfriend laughing about what a cheap "independent woman" she was, I called her.
“Did you hear that, Annie?” I asked, my voice cold.
“‘Independent woman’ is a trap. It’s a pedestal they put you on so they can enjoy the convenience of not having to provide a thing.”
“If you can use a man to get ahead, that’s a skill. Why wouldn’t you use it?”
She said nothing.
But the next day, I heard she finally kicked her cheapskate boyfriend of five years to the curb.
1
I became aware of my role in this story when I was very young. I knew I was the infamous gold digger, destined to use my beauty to climb a ladder of men, all for the sake of wealth and status.
My sister, Annie Ashton, was the righteous heroine. Taking help from a man was a mark of shame for her; she had to do everything herself.
The moment I understood her character design, I understood my own purpose. The author meant for me to be the foil, the dark reflection meant to prove a point: a woman’s life can only be built by her own two hands, never by relying on a man.
For a fleeting moment, I was disheartened, just a supporting character in someone else’s narrative. But the feeling passed. So I wasn’t the protagonist. It didn’t mean my life had to be worse.
If the author wanted so badly to condemn my choices, then I would show her a different way to live.
And so, armed with my own interpretation of what a "gold digger" could be, I began my life within the pages of this story.
2
The differences between Annie and me were obvious even in kindergarten. At five or six, kids are all about playing and making friends, and the currency of friendship was snacks.
Because we were identical and pretty, boys were always trying to give us candy.
Annie would meet their hopeful eyes with a blank stare and a firm rejection.
I, on the other hand, would always accept with a sweet smile.
Annie never understood. “Anya, you don’t even like sweets. Why do you take them?”
I looked at her and answered seriously. “Annie, they’re giving us snacks because they want to be our friends. They want us to say yes. Besides, their parents gave them those snacks to share. If they don’t give them to us, they’ll just give them to someone else. So why should we be ashamed to accept?”
She turned her head away, a flicker of uncertainty on her face. I knew she loved sweets. I knew she wanted to accept. But she was trapped by the role she’d been assigned, the "independent heroine" label she didn't even know she wore.
“Next time someone offers you something,” I urged her, “just take it. Think of it as a gift to start a friendship.”
Annie hesitated, then gave a small nod.
3
The next day, after school, a little boy approached Annie, his arms overflowing with snacks. He seemed to have gathered all his courage.
“Annie,” he whispered, “these are for you. Will you be my friend?”
I watched from the sidelines, curious to see what she would do. Annie looked from the boy to the mountain of treats in his hands. Her mouth opened as if to say no, but the word wouldn’t come out.
Finally, a decision seemed to form in her eyes. She reached out to take the snacks.
But a sharp voice cut through the air, stopping her cold. “Annie, what are you doing? You can’t just take things from boys!”
We both snapped our heads toward the kindergarten gate. Our parents were standing there, their faces masks of disbelief. They hurried over, pulled Annie away from the boy, and began their interrogation.
“Annie, how could you take snacks from a boy? At best, that’s just being greedy. At worst, it shows a complete lack of self-respect! A girl does not get things to eat by cozying up to boys!”
The little boy, his face burning red, scurried away.
Annie stood there, head bowed, as our parents lectured her. Several times, she glanced at me, her lips moving as if to speak, but she said nothing. She was probably wondering how we could have the same parents, yet I didn’t see this as a shameful act of a girl without self-respect.
4
After that incident, Annie became even more guarded. She refused all help and kindness from boys, determined to prove she could do everything on her own.
In middle school, we were in the same class. Annie’s grades were good, but her chemistry scores were mediocre, keeping her stuck in the middle of the pack. Her deskmate, Peter Vance, was a chemistry whiz and consistently ranked first in our year.
Peter, probably feeling sorry for his deskmate, tried several times to explain the problems she’d gotten wrong. Each time, Annie shut him down.
“Thanks, but I can figure it out myself.”
After a few attempts, Peter gave up.
In a way, Annie was right. In the story, Peter was a total player. Our plotlines were even supposed to intersect. After his crush on my sister went nowhere, he was meant to turn his attention to me, the girl who looked just like her. And I, seeing his good grades and wealthy family, was supposed to fall for him, convinced I’d found a guy with potential. I was supposed to get so wrapped up in the romance that my grades would tank, and I’d end up in a mediocre high school.
But a truly smart gold digger would never let that happen. I would take only what was useful from him and never let him distract me from my goals.
5
When Peter started showing interest in me, I didn’t push him away. Instead, I used his crush to my advantage, bringing him lists of problems I didn’t understand every day. After each tutoring session, I’d thank him with a small snack or a soda.
One afternoon, after I’d packed up my books, he took a sip of his Coke and finally asked the question that had been on his mind.
“Anya, why are you and your sister so different?”
I turned his question back on him. “How are we different?”
He tapped a long finger against his chin, thinking seriously. “She seems to hate relying on anyone. But you… you’re good at using people.”
I smiled as I zipped my backpack. “Peter, ‘using’ is such a harsh word. I prefer ‘leveraging.’ Only the most capable men offer a woman leverage. So, I’m not using you. I’m acknowledging your value.”
Peter had a big ego, and my words stroked it perfectly. He was completely won over.
“You know, Anya,” he said, a grin spreading across his face, “I don’t mind being used by you. But…” His tone shifted. “When are you going to be my girlfriend?”
I dangled a carrot. “When you help me get into Northwood Prep.”
He smirked, full of confidence. “Is that all?”
6
As it turned out, for Peter, it was that simple. With his help, six months later I passed the entrance exam for the most prestigious prep school in the state with the second-highest score in the city.
The first thing I did was block his number and all his social media accounts.
Annie, who had gotten into the same school through her own hard work, was appalled.
“You promised him you’d be his girlfriend if you got in. What do you call this?”
I just shrugged. “How many girls has Peter played with? Is it only okay for a guy to mess with a girl’s feelings, but not for a girl to use a guy to get ahead?”
Annie’s brow furrowed. “Anya, if you keep relying on men to succeed, you’ll regret it one day.”
“I don’t mind,” I said coolly. “The grades I got with his help were real.”
Annie looked at me like I was a lost cause.
Our relationship, while never incredibly close, had been decent enough. But after that, she started to distance herself from me. I understood. She was the story’s independent heroine; of course she’d look down on my methods.
We grew more and more estranged. It reached the point where people were shocked to learn we were sisters.
“Wait, Anya and Annie Ashton are sisters?”
“But they never even talk to each other at school!”
It was true. We didn’t speak at school, and we barely spoke at home.
7
At home, Annie was the sun around which our family revolved, thanks to her innate protagonist halo. I was usually just part of the background scenery.
Like tonight.
Our parents had prepared a feast to celebrate Annie getting first place in her class. That was the only time they’d bring me up.
“Anya, look at your sister. You scored higher than her on the entrance exam, but two years later, she’s at the top of the class. And you? Your grades are slipping. You’re not even in the top fifty anymore.”
Their words didn’t bother me anymore. I knew that even if I were number one, they wouldn’t spare me a single glance that wasn’t meant for Annie. I was just her foil, after all.
Annie, of course, didn’t see it that way. She thought it was all my own doing.
Later that evening, as I was heading to my room, she stopped me. Her expression was calm, tinged with the quiet pride of a winner.
“Do you see now?”
I looked at her, confused. “See what?”
“You can’t rely on other people forever. True security only comes from yourself. You used Peter to help you study and get good grades back then, but what about now? Are you going to rely on him for the rest of your life? If you start studying on your own now, it’s not too late.”
Her self-righteous sermon gave me a headache. Annie, did you really think I could have gotten those scores if I hadn’t been studying my ass off on my own? How dare you dismiss my hard work just because he helped me?
“And you probably don’t know this,” I said, changing the subject, “but I have a boyfriend now. We’re applying to universities abroad together. His family is covering all my expenses.”
Annie froze, her face shifting into a look of profound disappointment. “Anya, there’s no such thing as a free lunch. Everything has a price tag attached.”
I shrugged. “I don’t care.”
8
After that, Annie and I became complete strangers.
Honestly, I never wanted our relationship to get this bad. We weren't in direct competition, and I could understand her protagonist’s pride. Some of her warnings were even born from a genuine concern for me. But we were two extremes in this story, polar opposites, destined to drift apart over our irreconcilable views.
It was a shame, but I knew we could never convince each other. Perhaps being strangers was the best we could do.
As college entrance exams approached, I was a bundle of nerves, juggling exam prep and my study abroad applications. Everyone was in the final sprint.
And that’s when Annie got caught in a relationship.
The boy was Ryan Miller, a broke kid from her class with nothing to his name but a pretty face. The news sent shockwaves through the school administration. Annie was the top student in her year, the school’s only real hope for an Ivy League acceptance. They were terrified the relationship would tank her grades but were equally afraid that handling it badly would affect her performance.
So, they came to me, asking me to talk to her as her sister.
I refused at first. I knew she wouldn’t listen to me.
But Annie’s homeroom teacher told me that Annie often asked about my grades and my class rank. She insisted Annie cared about me, that I was the perfect person for the job.
So, one day after school, I waited for her outside her classroom.
9
When she saw me, a flash of surprise crossed her face before being replaced by her usual calm mask. “What are you doing here?” she asked.
I didn’t beat around the bush. “I heard you have a boyfriend.”
She nodded, unfazed. “So?”
“I just wanted to see what kind of guy would make you risk everything right before the biggest exams of your life. Annie, is he handsome? Is his family rich? What are his grades like?”
My words wiped the calm from her face, replacing it with a look of derision. “His family isn’t rich, and his grades are average. He’s not the type you’d be interested in. But so what? I’m not you. I don’t want anything from him. I believe I can get everything I want on my own, without needing a man.”
Her answer was exactly what I expected. The conversation was a dead end.
But as I turned to leave, I couldn't stop myself from looking back.
“Annie, the biggest mistake you can make with a man is to want nothing from him. It’s okay for you to have everything, but it’s not okay for him to have nothing.”
Her reply was ice-cold. “Thanks for the advice. I don’t need it.”
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