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
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.
For illustration purposes only. | Source: Midjourney
For illustration purposes only. | Source: Midjourney
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.
For illustration purposes only. | Source: Midjourney
For illustration purposes only. | Source: Midjourney
“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.”
For illustration purposes only. | Source: Midjourney
For illustration purposes only. | Source: Midjourney
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.
For illustration purposes only. | Source: Midjourney
For illustration purposes only. | Source: Midjourney
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.
For illustration purposes only. | Source: Midjourney
For illustration purposes only. | Source: Midjourney
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
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.
For illustration purposes only. | Source: Midjourney
For illustration purposes only. | Source: Midjourney
“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.
For illustration purposes only. | Source: Midjourney
For illustration purposes only. | Source: Midjourney
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
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.
For illustration purposes only. | Source: Midjourney
For illustration purposes only. | Source: Midjourney
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.”
For illustration purposes only. | Source: Midjourney
For illustration purposes only. | Source: Midjourney
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?”
For illustration purposes only. | Source: Midjourney
For illustration purposes only. | Source: Midjourney
“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
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.
For illustration purposes only. | Source: Midjourney
For illustration purposes only. | Source: Midjourney
“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.
For illustration purposes only. | Source: Midjourney
For illustration purposes only. | Source: Midjourney
“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.
For illustration purposes only. | Source: Midjourney
For illustration purposes only. | Source: Midjourney
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.
For illustration purposes only. | Source: Midjourney
For illustration purposes only. | Source: Midjourney
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.
For illustration purposes only. | Source: Midjourney
For illustration purposes only. | Source: Midjourney
“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.
For illustration purposes only. | Source: Midjourney
For illustration purposes only. | Source: Midjourney
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.”
For illustration purposes only. | Source: Midjourney
For illustration purposes only. | Source: Midjourney
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.”
Tell us what you think about this story, and share it with your friends. It might inspire them and brighten their day.
If you enjoyed this story, read this one: Charlie would have never thought that his daily hide-and-seek game with his older brother would reveal their parents’ family secret. A single paper with the word “Divorce” stopped the game for the boys and started a new mission: to save their parents’ marriage. Read the full story here.
This piece is inspired by stories from the everyday lives of our readers and written by a professional writer. Any resemblance to actual names or locations is purely coincidental. All images are for illustration purposes only. Share your story with us; maybe it will change someone’s life. If you would like to share your story, please send it to info@amomama.com.
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