Single mother Riley was trying her best to find love, even though it was tough. As soon as her dates found out she had a son, the romance quickly faded away. Her desperation grew, and Riley felt she had no choice but to hide her son. However, she immediately regretted that decision.
Riley stood in front of her 8-year-old son, Roy, with a heavy heart, unsure if she was making the right choice. At 32, balancing life as a single mother and trying to find love felt like walking a tightrope.
Ever since her ex-boyfriend walked out on her as soon as he found out she was pregnant, Riley had been left to raise Roy on her own.
For illustration purposes only. | Source: Midjourney
Over the years, she had embraced being a mom and built a world around her son, but deep down, there was still a longing—someone to share her life with, someone to love her as much as she loved Roy.
But finding that someone was harder than she ever imagined. Every time she met someone new, things seemed promising until they found out about Roy.
It was as if the mere mention of her child made them pull away. The disappointment stung every time, and Riley was growing tired of it.
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Now, with this new date on the horizon with Mitchell, she couldn’t shake the feeling that it was her last chance to see if there was hope.
Mitchell seemed different—kind, charming, and someone who could be the one. But she was afraid that if she introduced Roy too soon, she’d scare him off like the others.
“I don’t want to go to Kyle’s tonight,” Roy whined, clutching his favorite toy tightly in his arms.
His face was scrunched up in a pout, his big eyes pleading.
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“I want to stay here with you.”
Riley crouched down so that she was eye-level with her son, trying to push aside the guilt gnawing at her. She gently brushed a strand of hair off his forehead and forced a smile.
“Roy, it’s just for one night,” she said, trying to sound upbeat.
“You always have so much fun with Kyle. You two will stay up, watch movies, play games—it’ll be a blast. And I’ll pick you up first thing in the morning.”
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Roy’s expression softened slightly, but he still looked uncertain. “But what if I don’t want to sleep there?”
“You’ll be fine,” Riley reassured him. “It’s only for tonight, and tomorrow we’ll do something fun, okay?”
As much as she loved Roy, she needed this night to go well. She had arranged for him to have a sleepover at his friend Kyle’s house, something she rarely did. But tonight was different.
Tonight, she was going to see if there was a future with Mitchell, and to do that, she needed to focus on herself.
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She didn’t want to have to worry about Roy or the complications that might arise from mentioning she had a child too soon.
The taxi arrived at the Kyles house, and with one final hug, Riley sent Roy inside.
She felt a pang in her heart as she watched him walk up the steps, his shoulders slightly slumped, but she quickly reminded herself that this was necessary.
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She wasn’t doing this just for herself—if things went well with Mitchell, it could mean a better future for both of them.
As the taxi pulled away from Kyle’s house, Riley took a deep breath and tried to focus on the evening ahead.
She knew it wasn’t going to be easy, but she couldn’t help but hope that maybe, just maybe, this time would be different.
When Riley arrived at the restaurant, she spotted Mitchell waiting at a small table near the window. He looked sharp in a clean-cut suit, his hair neatly combed, and when he saw her approaching, his face lit up with a warm smile.
For illustration purposes only. | Source: Midjourney
Riley’s nerves immediately kicked in, but she had put effort into her appearance tonight—her favorite dress, just enough makeup to feel confident, and a pair of heels that made her feel taller.
She wanted to feel good about herself, especially since she was hoping this date could be something more than just casual.
They exchanged a few pleasantries as they sat down, but there was an awkward tension in the air.
Neither of them seemed to know what to say to get the conversation going. Riley’s mind raced as she tried to think of a topic to break the ice, but Mitchell beat her to it.
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“So, do you think the menu is a bit too… fancy?” Mitchell asked, a playful smile on his face. “I mean, I’ve never seen so many different kinds of salad in my life.”
Riley couldn’t help but laugh. The tension broke, and the joke made her feel more at ease.
“I know, right? Who knew you could have six varieties of lettuce?” she joked back.
With that, the conversation flowed more easily. They started talking about their favorite foods, funny stories from their jobs, and some light-hearted moments from their past.
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Riley found herself laughing more than she had in months, and for a while, she felt like she could enjoy the evening without overthinking everything.
But as they finished dinner and stepped outside for a walk, that nagging thought crept back into her mind. She still hadn’t told him about Roy.
The guilt weighed on her. She liked Mitchell, and they were getting along so well, but would that change if he knew she was a single mother?
For illustration purposes only. | Source: Midjourney
Taking a deep breath, Riley decided to test the waters.
“Mitchell, what do you think about kids?” she asked, trying to sound casual but feeling her heart race as she waited for his answer.
Mitchell’s expression shifted slightly. He hesitated for a second and then quickly changed the subject.
Riley’s heart sank. His avoidance was clear, and it made her even more anxious about telling him the truth.
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She didn’t want to lose this connection, but hiding such a big part of her life felt wrong.
Before she could figure out what to say next, her phone buzzed in her pocket. Startled, she quickly excused herself and answered. It was Kyle.
“Kyle? Is everything okay?” she asked, trying to hide her rising worry.
Kyle’s voice was shaky. “Roy fell really bad, and he won’t stop crying. You need to come get him.”
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Riley’s heart leaped into her throat. Her son needed her, and there was no question in her mind about what she had to do next.
Riley took a deep breath, her heart pounding as she turned to Mitchell. She knew she couldn’t avoid the truth any longer.
“Mitchell, I need to tell you something,” she said, her voice slightly trembling.
Mitchell looked at her with genuine concern in his eyes. “What is it?”
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“I have an 8-year-old son, Roy,” Riley admitted, the weight of the words hanging in the air. “I didn’t tell you earlier because… I was afraid it would scare you away.”
She paused, gauging his reaction. His face showed a hint of surprise, but he remained silent, letting her continue.
“I left him at his friend’s house tonight so we could have some space, but he just got hurt, and I need to go get him. I’m so sorry. I lied, and I shouldn’t have done that.”
For illustration purposes only. | Source: Midjourney
Mitchell stared at her for a few moments, and Riley braced herself for the worst. But then, he smiled softly, the corners of his eyes crinkling in a way that reassured her.
“Riley, it’s okay,” he said gently. “I understand. And honestly, I’ve been hiding something too.”
Riley blinked, caught off guard. “What do you mean?”
Mitchell let out a small sigh, running a hand through his hair.
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“I have a daughter. She’s twelve. I didn’t mention her because I was afraid of how you’d react too.”
Riley’s heart lifted with relief. “You do?” she asked, her voice softening with surprise. She hadn’t expected this.
Mitchell nodded.
“Yeah, and I get it, Riley. Being a parent is tough. You’re constantly juggling everything, trying to make sure your kid is okay while also trying to live your own life. Dating is even harder when you’re trying to balance it all.” He smiled warmly at her.
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“Why don’t I come with you? We can go get Roy together. I’d like to meet him.”
Riley’s eyes welled up with gratitude, a mixture of relief and joy washing over her.
She had been so scared of telling him, of being judged, but here he was, offering to help.
“You’d do that?” she asked, her voice barely above a whisper.
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Mitchell smiled again, his expression calm and reassuring. “Of course. I know how important he is to you. Let’s go make sure he’s okay.”
Riley couldn’t believe how everything had turned out. She smiled back at Mitchell, feeling a sense of peace she hadn’t felt in a long time. Together, they headed to the car, ready to get Roy.
Mitchell drove Riley to Kyle’s house, his hands gripping the steering wheel a little tighter than usual. Riley sat beside him, her mind racing with worry about Roy.
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They barely exchanged words, but Mitchell’s presence was comforting. As soon as they arrived, they both hurried to the front door, their nerves apparent in their quick steps.
Kyle’s mother greeted them with a calm expression, clearly puzzled by their urgency. “Is everything alright?” she asked, looking from Riley to Mitchell.
“Kyle called and said Roy was hurt,” Riley explained, her voice trembling with concern.
Kyle’s mother’s brow furrowed in confusion, but she remained calm.
“Oh, I’m sure he’s fine. The boys are just upstairs, playing video games. Come on, I’ll show you.”
Riley and Mitchell followed her upstairs, hearts pounding, though the woman’s calm demeanor reassured them slightly.
When they reached Kyle’s room, Riley pushed the door open carefully, bracing herself. There, sitting on the floor, were Roy and Kyle, engrossed in their game, completely unharmed.
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Relief washed over Riley as she knelt in front of Roy, her voice soft but full of concern. “Roy, what happened? Kyle said you were hurt.”
Roy blushed deeply, fiddling with the controller in his hands. “I… I just missed you, Mom. I wanted you to come back.”
Riley’s heart melted. She pulled Roy into a tight hug, tears welling up in her eyes. “Oh, Roy. You don’t have to make up stories to see me. I’ll always come back for you, no matter what.”
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Behind her, Mitchell chuckled softly, the tension in the air dissolving. “Well, looks like the crisis has been averted,” he said with a grin.
As they drove home, Riley couldn’t help but laugh at how the night had turned out. All the stress and fear had vanished, replaced by the warmth of the moment.
She glanced at Roy, who was happily chatting away in the back seat, and then over at Mitchell, who smiled at her.
“How about our next date?” Mitchell asked, his eyes twinkling. “We bring the kids.”
Riley smiled back, her heart light. “I’d like that.”
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Man from Dating Site Brought His Parents on Our First Date with Their Ridiculous Demand – I Decided to Outplay Them
Who brings their parents to a first date? My boyfriend from a dating app did. But what really got me was the list of OUTRAGEOUS DEMANDS his parents brought with them. I knew I’d have to outwit them… but on my own terms.
When I virtually met Jacob on a dating site several months ago, we hit it off instantly. The connection felt real — the kind that makes your heart skip a beat when you see a new message notification. I grew to think that he was “the one,” but then when we actually met… well, let’s just say reality has a way of shattering our perfectly crafted illusions.
A woman holding a phone | Source: Unsplash
Three months of late-night texts and hour-long video calls had built up to this moment. Jacob wasn’t just another match; he was different.
While most guys led with cheesy pickup lines or bland “hey” messages, he had caught my attention with a detailed comment about my profile photo taken at Comic-Con.
“Is that a handmade Scarlet Witch costume?” he’d written. “The detail work is incredible!”
From there, our conversations flowed naturally. He listened, really listened, when I talked about my work as a graphic designer and my dreams of starting my own studio.
A woman using a computer | Source: Midjourney
He shared my love for true crime podcasts and could quote every episode of my favorite shows by heart. When I mentioned my sister’s battle with depression, he opened up about his own experiences with anxiety.
“I feel like I can tell you anything,” he’d said during one of our video calls, his warm brown eyes crinkling at the corners. “I’ve never connected with someone like this before.”
“Me neither,” I’d admitted, feeling my cheeks flush. “Sometimes I worry this is too good to be true.”
He’d laughed then, running a hand through his dark hair. “I can’t wait to finally meet you in person. Friday at Coffee Beanz? 7 p.m.?”
A man using a laptop | Source: Pexels
“It’s a date! Finally!” I’d chirped, unable to contain my excitement.
“See you on Friday!” He said as I hung up, blushing.
I spent the entire week planning my outfit, finally settling on a gorgeous dress that my best friend Sarah insisted brought out my eyes.
“He won’t know what hit him,” she’d said, helping me style my hair.
Friday evening found me standing outside Coffee Beanz, smoothing down my dress for the hundredth time. Through the window, I could see couples enjoying their meals, soft candlelight flickering across their faces.
People in a cafe | Source: Unsplash
My hands were shaking slightly as I pushed open the heavy wooden door, the warm aroma of garlic and fresh bread enveloping me. My eyes nervously darted around in search of Jacob.
“Lia! Over here!”
I turned toward Jacob’s familiar voice, my practiced smile freezing on my face. There he sat, but not ALONE.
An older couple sat beside him, their faces beaming with smiles. My heart, which had been filled with excitement all day, sank to my stomach.
“Hey… um, hi, what’s going on?” I managed, my brain struggling to process the scene before me.
A shocked woman | Source: Pexels
Jacob stood up, his bright smile unchanged as if this was completely normal. “Lia, I’m so excited to finally meet you! These are my parents, Linda and Patrick!”
Linda, a petite woman with perfectly coiffed gray hair and gold earrings that probably cost more than my monthly rent, gave me a practiced smile that didn’t reach her eyes. Patrick, sporting a dress shirt that seemed a size too small for his frame, barely looked up from his menu.
“Sit down, girl,” Linda patted the chair next to her, not next to Jacob. “While we wait for our appetizers, I have a few questions for you.”
An older lady smiling | Source: Midjourney
I sank into the chair, still trying to make sense of this ambush. The waiter appeared with water glasses, and I found myself wishing it was something stronger.
That’s when Linda pulled out a crisp sheet of paper from her designer handbag.
“Now then,” she cleared her throat, clicking her gold-plated pen. “I’ve prepared a brief questionnaire to help us get to know you better. I want you to fill it out.”
Sheets of paper on a table | Source: Pexels
My eyes scanned the paper she placed before me, each question worse than the last:
1. What is your current annual income and five-year career projection?
2. Please list any medical conditions, including a family history of genetic disorders.
3. How many romantic partners have you had, and what were the reasons for those relationships ending?
4. Do you own or lease your vehicle? What is your credit score?
5. Are you willing to sign a prenuptial agreement?
6. Do you plan to work after having children? If so, who will provide childcare?
7. What is your stance on living with in-laws?
8. Are you willing to host special occasions like Thanksgiving & Christmas every year without expecting a penny from your partner?
A startled woman covering her mouth | Source: Pexels
The questions went on and on like a never-ending train carriage. My water glass stopped halfway to my mouth. “I’m sorry, but is this for real?”
“Of course it is, dear,” Linda replied, her tone suggesting I was being deliberately difficult. “Our family has certain standards to maintain. We need to ensure any potential partners for our Jacob are… suitable.”
My eyes darted to Jacob, waiting for him to jump in, to say this was all a joke. But he just sat there, examining his napkin as if it held the secrets of the universe.
A man sitting casually | Source: Midjourney
Something snapped inside me. Three months of building this connection, sharing hopes and fears, only to be treated like a job applicant? No. This called for a different approach.
“Would you excuse me for just a moment?” I smiled sweetly. “Ladies’ room.”
Instead of heading to the restroom, I ducked into the convenience store next door. Five minutes later, I returned with my own notebook and pen.
“Before I answer your questions,” I said, sitting down with renewed confidence, “I have a few of my own.”
A woman holding a piece of paper | Source: Pexels
Linda’s perfectly plucked eyebrows shot up in surprise as I placed the paper with my questions on the table. She picked it up and began reading loudly, her face speaking volumes of her anger.
“Question one: At what point did you realize your son wasn’t capable of choosing his own partner?”
Patricks’s face reddened. Jacob finally looked up from his napkin.
“Question two: How many women have actually completed your interrogation process? Or do most run screaming before the credit check?”
“This is completely inappropriate!” Linda’s voice pitched higher as she continued to read.
A furious older woman with a man | Source: Midjourney
“Question three: Do you also inspect their teeth like show horses, or is that saved for the second date?”
“Question four: When Jacob moves out of your basement, will you be requiring his future wife to submit weekly progress reports?”
“Question five: Have you considered therapy for your control issues, or is that too personal a question?”
“That’s enough!” Jacob slammed his hand on the table, making the silverware jump. “You have no right to disrespect my family like this!”
An angry man | Source: Midjourney
I leaned back, crossing my arms. “Oh, but they have every right to treat me like I’m applying for a position at the FBI?”
“My parents are just looking out for me,” he protested, his voice weak. “They want what’s best— “
“No, Jacob. What’s best for you would be growing a backbone and living your own life.”
Linda and Patrick were already gathering their things, faces flushed with indignation. Linda’s hands shook as she stuffed her questionnaire back into her bag.
“We’re leaving,” she announced. “Jacob, come on. She’s not the one for you.”
“Wait!” I called out, loud enough for nearby tables to turn. “Aren’t you forgetting something?”
Side shot of a woman | Source: Midjourney
They paused. “WHAT??”
“Waiter, these people are trying to leave without paying their bill!” I announced loudly, waving to the waiter. “Guess running out on checks is another proud family tradition!”
The restaurant had gone quiet. Linda’s hands shook as she pulled out her credit card, practically throwing it at the waiter. I stood up, smoothing my dress once again.
“Well, this has been entertaining. I’ll cover my water.” I placed a five-dollar bill on the table and turned to Jacob.
“Good luck finding someone who meets your family’s rigorous standards. Although, you might want to try job recruitment sites instead of dating apps. I hear they provide detailed background checks and references.”
A woman laughing | Source: Midjourney
As I walked out into the cool evening air, my phone buzzed with a message from Jacob, “You didn’t have to be so cruel. My parents were just looking out for me.”
I typed back, “Just looking out for myself, mama’s boy. Goodbye!”
Later that night, Sarah called to hear about the date. After I finished telling her everything, she was quiet for a moment.
“You know what?” she finally said. “I bet Linda has a spreadsheet ranking all of Jacob’s potential wives.”
We both burst out laughing, and I felt the last of my disappointment melt away. Dodged a bullet? Absolutely. And I’ve never been so grateful for a red flag wrapped in a questionnaire.
A woman walking away | Source: Midjourney
This work is inspired by real events and people, but it has been fictionalized for creative purposes. Names, characters, and details have been changed to protect privacy and enhance the narrative. Any resemblance to actual persons, living or dead, or actual events is purely coincidental and not intended by the author.
The author and publisher make no claims to the accuracy of events or the portrayal of characters and are not liable for any misinterpretation. This story is provided “as is,” and any opinions expressed are those of the characters and do not reflect the views of the author or publisher.
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