Rich Man Falls in Love with Homeless Girl He Sees on the Street and Rushes to Find Her — Story of the Day

He saw a girl begging on the sidewalk and somehow couldn’t get her face out of his mind. He had to know her story.

Wealthy businessman Roger Landers was often annoyed by the sight of the homeless begging on the street outside his office building. There seemed to be more and more of them each year, he reflected.

As he passed a young woman huddled against a wall, a kindly soul dropped a coin in her cup. The woman looked up and smiled at her benefactor and that smile pierced Roger to the heart. In one second, that huddled anonymous annoyance became a lovely radiant woman.

For illustration purposes only. | Source: Unsplash

For illustration purposes only. | Source: Unsplash

Roger walked into the building and that moment when the girl’s face was transformed by her smile replayed over and over in his mind. He found himself wondering who she was, what had driven her to live in the pitiless streets of L.A.?

For the rest of the week, Roger found himself almost obsessed by the young homeless woman. He watched her surreptitiously, and once when he dropped a coin in her cup, watched that miraculous transformation at close quarters.

Love can sometimes lurk in the most unexpected places.

He found himself thinking about her, inventing stories about her, little fantasies in which he discovered she was really a reporter writing about homelessness at close hand, or a deeply committed actress preparing for a role…

Finally, on Friday afternoon, after he wrapped his work for the day and dismissed his employees, Roger did what he’d been longing to do all week. He walked up to the girl sitting on the sidewalk and talked to her.

For illustration purposes only. | Source: Unsplash

For illustration purposes only. | Source: Unsplash

“Hi,” he said awkwardly. “Would it be okay if I bought you a cup of coffee? You look really cold.” The girl lifted up her face and smiled at him.

“Thank you,” she said sweetly. “I’d like that.” Roger was struck by her low educated voice and her grace as she got to her feet. She was tiny, he realized, a petite 5′ 3″ next to his towering 6′ 2″.

He walked her to a nearby coffee shop and ordered her hot food to go with her coffee. Once again Roger was surprised by her delicate gestures, her manners. This was an educated girl. How had she ended up on the streets?

When Roger saw color flood back into the girl’s face after she finished her hot soup, her grilled sandwich, and her coffee, he asked her exactly that. “How did this happen to you? Living on the streets?”

The girl looked him straight in the eye. A wry smile twisted her lips. “I was stupid, and trusting,” she said. “It’s not an original story. I was in love with this boy in my hometown — Idaho — if you can believe it.

For illustration purposes only. | Source: Unsplash

For illustration purposes only. | Source: Unsplash

“My parents disapproved of him, which only made him even more romantic and attractive to me… To cut a long story short, he convinced me to withdraw my college funds and run away with him to L.A. He was going to be a movie star, and I’d be a screenwriter…”

Roger shook his head sadly. “A lot of people come out here every year, less than a handful make it!” he commented.

“Well, I’ll never know.” A tinge of bitterness colored the girl’s voice. “The first night in L.A., we booked into a motel. When I woke up in the morning Kevin was gone, so was my money and everything I had.”

Roger gasped. “Did you go to the police? Call your family?” The girl was shaking her head, tears in her eyes.

“I was too ashamed. I made a deal with the motel manager. She let me sleep in the storeroom and I cleaned the rooms. Some of the guests gave me tips, and I managed to eat. But then her husband started trying…” The girl shook her head. “You know how it is. I left the motel and ended up here, on the streets.”

For illustration purposes only. | Source: Pixabay

“What’s your name?” Roger asked gently.

“Emma,” the girl said with one of those radiant smiles. “Emma Sinclair from Preston, Idaho!”

“Well, Emma Sinclair from Preston, Idaho,” Roger smiled back. “I’m Roger Landers from Los Angeles, California, and I’m sending you home.”

Roger took Emma into a nearby mall and he bought her several outfits and a suitcase. He waited at the food court while she changed and came out of the restroom transformed.

He drove her to the bus station and bought her a bus ticket home. He tucked a $100 bill in her hand. “Listen,” he said. “Don’t let any more charming rascals talk you into coming to L.A., OK?”

For illustration purposes only. | Source: Unsplash

For illustration purposes only. | Source: Unsplash

Emma was crying and smiling through her tears. She reached up and gave Roger a hug. “Thank you, thank you, and God bless you!”

Roger watched her board the bus with a sinking feeling in his heart. Why did he feel that this was a mistake? He wanted to run after that bus, beg Emma to stay… What was happening to him?

That night, Roger realized that the petite waif with the glowing smile had stolen his heart. “If I let her go, I’ll regret it for the rest of my life!” he told himself. “She’s special, and I love her.”

Two days later, Roger was driving into Preston, Idaho. He stopped at the police station and asked where he could find Emma Sinclair. “Emma?” asked one of the deputies suspiciously. “What do you want with Emma?”

For illustration purposes only. | Source: Unsplash

For illustration purposes only. | Source: Unsplash

Roger blushed. “Well, you see, I met her in LA, and I wanted to see if she was alright…”

The deputy looked him up and down. “You can find Emma at her mom’s laundromat, two doors down. I’m coming with you. I don’t want any more trouble for Emma!”

Roger’s heart was beating fast as he walked into the laundromat and saw Emma. She looked up and her face lit up. At that moment, Roger knew she had been feeling the same way: they belonged together!

So just three weeks after she returned home, Emma headed back to LA once again, but this time she was with a man who loved and cherished her. By the end of the year, Roger and Emma were married, and she became involved in a program to help runaways find their way home.

For illustration purposes only. | Source: Unsplash

For illustration purposes only. | Source: Unsplash

What can we learn from this story?

  • Helping others can be a transformative experience. Roger helped Emma, and in the process, he found his own way to life-long happiness.
  • Love can sometimes lurk in the most unexpected places. Roger found love with a homeless waif when everyone expected him to marry a socialite.

My Son Drew Pictures of a Strange Man — When I Asked Him, He Said, ‘He Comes to See Mommy When You’re at Work’

I was stunned when my son started drawing a grinning stranger. “He comes to see Mommy when you’re at work,” Oliver said innocently. Initially dismissing it as a childish fantasy, I soon spied a mysterious man entering our home, igniting a chilling quest for the truth.

I found the drawing while tidying up the dining table. Most of Oliver’s pictures were what you’d expect from a six-year-old: dinosaurs with rainbow scales, our house with a chimney that looked more like a volcano, and stick figures of our family holding hands. But this one made me pause.

A man frowning at a drawing | Source: Midjourney

A man frowning at a drawing | Source: Midjourney

Among the crayon scribbles was a tall figure with unnaturally long arms and huge hands, wearing what looked like a suit. The figure had an enormous grin that stretched across most of its face.

“Oliver,” I called out, trying to keep my voice casual as my fingers crinkled the edge of the paper. “Is this me in the picture? Who is this?”

My son looked up from his LEGOs, his blue eyes bright with excitement.

An excited boy with a bright smile | Source: Midjourney

An excited boy with a bright smile | Source: Midjourney

The plastic blocks clattered as he dropped them onto the hardwood floor. “That’s Mr. Smiles, Daddy! He’s Mommy’s new friend. He comes to see her when you’re at work.”

My heart skipped a beat. Laura and I had been married for nine years. We’d had our ups and downs like any couple, weathered job changes and family losses, and celebrated promotions and birthdays. But never, not once, did I think she’d…

No, I shook the thought away. There had to be a reasonable explanation. Laura wasn’t that kind of person. We’d built too much together.

A concerned man holding a paper | Source: Midjourney

A concerned man holding a paper | Source: Midjourney

“When does he come over?” I asked, proud of how steady my voice remained despite the tremor in my hands.

Oliver stacked another block on his tower, his tongue poking out in concentration.

“Sometimes in the morning. Sometimes at night. He always makes Mommy and me laugh.” He glanced up, suddenly serious, his small face scrunching with the weight of importance. “But, Daddy, it’s a secret! Don’t tell anyone!

An emotional man standing in a living room | Source: Midjourney

An emotional man standing in a living room | Source: Midjourney

The mention of laughter and secrecy felt like ice in my stomach.

That night, I barely slept, watching Laura’s peaceful face in the darkness. The steady rhythm of her breathing, once comforting, now felt like a taunt. Every time she shifted in her sleep, I wondered what she was dreaming about. Who she was dreaming about.

The next day, I left work early, parked down the street from our house, and waited. The fall air grew crisp as the afternoon wore on, and fallen leaves skittered across my windshield. A little after 3 p.m., a sleek black car pulled into our driveway.

A black car parked in a driveway | Source: Pexels

A black car parked in a driveway | Source: Pexels

A tall, wiry man stepped out and marched up to the front door. Even from this distance, I could see his broad smile when Laura welcomed him inside. The door closed behind them.

I gripped my steering wheel until my knuckles turned white; the leather creaking under my fingers.

“Maybe this is all in my head,” I whispered to myself, watching my breath fog the window. “But if I’m wrong, I need to know for sure.”

A man sitting in a car | Source: Pexels

A man sitting in a car | Source: Pexels

Over the next few weeks, I started buying Laura flowers and gifts, trying to rekindle our bond, but I also began documenting everything.

The evidence piled up: receipts for dinners I didn’t attend, calls she’d leave the room to take, and, of course, more pictures of “Mr. Smiles” drawn by Oliver. Each new piece of evidence felt like another brick in a wall being built between us.

Laura noticed the change in me.

A woman staring at her husband during dinner | Source: Midjourney

A woman staring at her husband during dinner | Source: Midjourney

“Are you feeling okay?” she asked one day, touching my forehead with concern. “You seem distracted lately.”

The genuine worry in her voice only confused me more. How could she act so normal if she was hiding something so huge?

“I… do you have someone else?” I asked.

“Someone else?” Laura stared at me with wide eyes, then shook her head.

A woman looking at her husband with wide eyes | Source: Midjourney

A woman looking at her husband with wide eyes | Source: Midjourney

“Of course not, honey!” She let out a little chuckle. “How could you think that?”

Maybe I should’ve confronted her then, but all my evidence was circumstantial. I needed cold, hard proof.

One Friday evening, I told Laura I’d be working late. Instead, I set up a hidden camera on the bookshelf in the living room and watched the feed from my car parked around the corner.

A bookshelf in a living room | Source: Pexels

A bookshelf in a living room | Source: Pexels

The screen of my phone cast a blue glow across my face as I waited, my coffee growing cold in its cup holder.

Right on schedule, Mr. Smiles arrived, and Laura greeted him with that same warm smile that used to be reserved for me.

But then something strange happened. He didn’t settle on the couch or share a private dinner. Instead, my sister walked in, and Oliver came bounding down the stairs with a beaming smile. More people arrived: neighbors and friends!

A man looking at his phone in confusion | Source: Midjourney

A man looking at his phone in confusion | Source: Midjourney

They all knew about this? And worse, they were having a secret get-together! I watched in stunned silence as Mr. Smiles, now wearing a festive party hat, juggled three oranges for Oliver and made him laugh.

“What the heck is going on?” I muttered, fumbling with my car door.

Rage and confusion propelled me toward the house. The evening air felt thick and heavy as I stormed up our front walk. I burst through the front door, making everyone freeze mid-conversation, the cheerful music cutting off abruptly.

A group of people in a living room staring at someone in surprise | Source: Midjourney

A group of people in a living room staring at someone in surprise | Source: Midjourney

“Alright, you won,” I said, my voice trembling. “Everyone here knew, didn’t they? Even Oliver? Even my sister?”

“No, no! Please, stop!” Laura’s face had gone pale, her hands clutching a roll of streamers that cascaded to the floor.

I turned to Mr. Smiles, who had stopped juggling and was staring at me with wide eyes.

“You’ve disrespected me as a man, and you’ve got no business being here! It’s my house! It’s my…”

My voice trailed off as I spotted something shiny on the floor.

A man speaking angrily to someone | Source: Midjourney

A man speaking angrily to someone | Source: Midjourney

A banner, not yet hung, with golden letters that read “Happy 10th Anniversary!” The metallic paper caught the light from our living room lamps, throwing sparkles across the ceiling.

The room went completely silent. Laura’s hands covered her mouth, tears welled in her eyes, and she smudged her carefully applied makeup. Mr. Smiles cleared his throat and stepped forward, his famous grin nowhere to be seen.

“Sir, I think there’s been a misunderstanding,” he said softly, his professional demeanor never wavering. “I’m a wedding planner and party animator. Your wife hired me months ago to plan this event — your wedding anniversary!”

A man speaking in a living room | Source: Midjourney

A man speaking in a living room | Source: Midjourney

“You thought I was cheating on you?” Laura’s voice cracked with hurt and disbelief, each word falling like a stone between us.

I felt the floor shift beneath my feet. The room suddenly seemed too bright, too crowded, the decorations garish and mocking.

“I… I didn’t know what else to think,” I stammered, my collar feeling too tight. “I saw him coming here, and Oliver said a man kept visiting while I was at work, that this man made you laugh…”

An emotional man looking confused and shocked | Source: Midjourney

An emotional man looking confused and shocked | Source: Midjourney

“Oliver said he made me laugh because he does magic tricks for him when we plan,” Laura interrupted, her voice rising. “I was trying to do something special for you, and you thought I was unfaithful?”

My throat felt tight. “I’m sorry,” I managed to say, the words feeling inadequate. “I was wrong. I let my insecurities get the better of me.”

Laura wiped her eyes with the back of her hand, leaving a dark smudge of mascara. “How could you think that? After everything we’ve been through?”

An emotional woman speaking to her husband | Source: Midjourney

An emotional woman speaking to her husband | Source: Midjourney

The party guests began quietly filing out, murmuring awkward goodbyes, their shoes shuffling across our carpet.

My sister squeezed my shoulder as she left, whispering, “Fix this.” Oliver looked confused and scared, so Laura’s mother took him upstairs to his room, their footsteps echoing in the tense silence.

When we were finally alone, Laura sat on the couch, her shoulders slumped. The streamers lay in tangles around her feet.

An upset woman sitting on a sofa | Source: Midjourney

An upset woman sitting on a sofa | Source: Midjourney

“I spent months planning this,” she said quietly. “I wanted it to be perfect. Remember our first anniversary? When you surprised me with that picnic in the park? I wanted to do something just as special.”

I sat beside her, careful to leave space between us, the cushions dipping under my weight. “I ruined everything.”

“Yes, you did.” She turned to look at me, her eyes red but fierce. “Trust isn’t just about believing in someone when everything’s perfect. It’s about believing in them when things don’t make sense.”

“I know,” I whispered, feeling the weight of my mistake. “I forgot that somewhere along the way. Can you forgive me?”

A couple having a serious conversation | Source: Midjourney

A couple having a serious conversation | Source: Midjourney

Laura was quiet for a long moment, her fingers tracing patterns on the fabric of her dress.

“I love you,” she said finally. “But this isn’t something I can just get over. You need to understand how much this hurts.”

I nodded, feeling tears start to fall. “I’ll do whatever it takes to make this right.”

“It won’t happen overnight,” she warned, her voice stern but not unkind.

A stern-looking woman speaking to someone | Source: Midjourney

A stern-looking woman speaking to someone | Source: Midjourney

“I know. But I’m not going anywhere.” I reached for her hand, and after a moment’s hesitation, she let me take it, her fingers cool against my palm. “Happy anniversary,” I said softly.

She gave a watery laugh that held both forgiveness and reproach. “Happy anniversary, you idiot.”

Upstairs, we heard Oliver laughing at something, probably one of his grandmother’s stories. The sound filled our living room, reminding us of all we had to lose, and all we had to save.

A couple in a living room glancing upwards | Source: Midjourney

A couple in a living room glancing upwards | 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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