“Get a job!” That’s what Leo would say to a homeless person. It’s amusing, really, because Leo had never worked a day in his life. He was born with a silver spoon in his mouth. With a rich family background, he had everything except real friends. But his life was about to teach him what money couldn’t buy.

Leo was relaxing in the back seat of a plush Cadillac, feeling on top of the world.

He was all dressed up in a fancy suit, his wrist heavy with a shiny watch that caught the light with every movement.

He leaned back, a smug grin on his face as he read an article on his phone. It was all about his father, Richard, being the wealthiest man in the city.

Leo’s smile widened as he scrolled through the article, indulging in the reflected glory of his father’s success.

“See this, Bob?” he yelled at his driver, showing him the phone. “Another article about my father. He’s quite the celebrity.”

“Yes, indeed, it’s a remarkable article, Mr. Leo,” Bob replied, his eyes fixed on the road, as reserved as ever.

Leo exaggeratedly sighed, his eyes rolling.

“Sure, he’s rich, but he’s stingy when it comes to buying his son a new car. Unbelievable, huh?”

Bob shot him a sideways glance through the rearview mirror, a faint smile touching his lips.

“With all due respect, sir, that would be your third car.”

Leo huffed, rolling his eyes once more.

“You sound just like him, Bob.” His tone was edged with irritation as his gaze drifted to the window, seeking something more entertaining.

At a red light stop, Leo’s eyes caught sight of a woman by a table loaded with clothes.

People surrounded her, carefully choosing items. Leo squinted in curiosity.

“Stop the car! What’s going on over there?”

Bob pulled over, observing the scene.

“I believe they’re distributing clothes to those in need, sir,” he explained.

Leo rolled his eyes again and grumbled.

“They don’t need help; they need jobs…” He mocked, rolling down his window to jeer at the woman.

“Hey, lady!” he shouted with a mocking grin.

“Feeling lonely enough to start bribing homeless people?” He chuckled at his own so-called wit.

The woman looked his way, her demeanor serene and composed.

She chose silence, turning her attention back to those she was aiding. Her quietness only seemed to amuse Leo more.

“Perhaps you’re interested in an evening with a real man?” Leo called out, his voice thick with sarcasm.

“I can arrange that!”

He laughed heartily at his own words and then rolled up the window, feeling quite pleased with himself.

Bob cleared his throat, maintaining a neutral expression.

“Sir, I’d be cautious. Your father might not take kindly to such behavior being noticed by others.”

“Oh, lighten up, Bob. It’s just a laugh!” Leo dismissed casually, chuckling.

“What’s the worst that could happen? A group of ragged folk coming after us?”

He laughed uninterested, and Bob, ever loyal, nodded and drove on, though his thoughtful look lingered after they left.

The following morning, Leo was comfortably asleep, sprawled across his luxury bed, completely oblivious to the storm brewing.

His peaceful dreams shattered as ice-cold water splashed over his face, jolting him upright. He rubbed his eyes, bewildered.

“What the heck!?” he yelled, searching wildly for who was responsible.

Standing at the edge of the bed was his father, Richard, arms folded and a serious expression on his face.

“Unfortunately, a splash of water doesn’t change the fact that you’re entitled,” Richard declared, his voice lined with disappointment.

“Dad? What’s happening?” Leo stammered, shocked.

Richard held up his phone, jaw tight.

“You’re what’s happening,” he said, shoving the phone at Leo.

The screen showed an article from local news. Leo squinted, still groggy, and read the headline aloud.

“…The spoiled heir of the richest family mocks a volunteer aiding the homeless?” Leo’s voice faded as a sinking feeling took over. “Is…is this about me?”

“Why do you consistently embarrass and make our family a laughingstock?” Richard asked, his voice level yet icy.

Leo shrugged, trying to brush it off.

“Come on, Dad, it was just some homeless folks and a stranger—they don’t matter.”

Richard’s face grew stern as he slowly shook his head.

“I’ve raised a real jerk,” he murmured, almost to himself. “I can’t support this behavior any longer.”

“What do you mean?” he asked, panic rising in his voice.

“All your bank cards have been blocked,” Richard stated flatly.

“What!? You can’t do that!” Leo’s voice splintered with disbelief.

“It’s done,” Richard affirmed, his tone unwavering. “And you must leave this apartment today.”

“But… I’m your son!” Leo shouted, desperation dripping from his words.

“Indeed, and all you’ve done is squander money and tarnish my reputation. Prove you deserve to bear my name.”

Leo was at a loss for words. His father, his perpetual safety net, was serious this time.

“How do I do that?” Leo finally asked, his voice small.

“Start by apologizing to the volunteer you mocked. Make sure the press catches wind of it, and I might consider giving you a second chance.”

“This is absurd!” Leo protested, anger sparking. But he saw the finality in his father’s eyes.

Without another word, Richard turned and left, leaving Leo soaked and stunned.

In just one day, Leo’s life flipped from a cushy, carefree existence to facing the harsh reality he’d sneered at. Now, he was about to experience a world he once derided.

Leo found himself back on that familiar street, the very one he had so proudly driven down in his father’s Cadillac the day before.

Today, however, he was on foot, head low, feeling the sting of shame and bitter disappointment.

He wore a plain jacket, his hood up, trying to remain unseen, unsure if it was out of embarrassment or cold.

As he approached where he’d seen the volunteer previously, he hesitated.

The woman stood there, smiling warmly at everyone she interacted with, her table still brimming with clothes.

“Hi…” he managed, barely audible.

She raised her eyebrows, a light smirk forming.

“Well, hello, ‘real man.’ Low on clothes today?” Her tone was playful but carried an edge.

“My name’s Leo…” he began, striving for politeness.

“That much I know,” she replied, her arms folding.

“I’m Gwen, and I’m not particularly impressed to make your acquaintance.”

“Alright, Gwen, listen. I’m sorry for what I said,” he said, forcing himself to look her in the eye. “I was wrong.”

“Okay,” she replied nonchalantly as though his apology was just another moment in her day.

Leo felt a slight relief.

“Great! So, could you maybe… I don’t know, tell the newspaper it was just a misunderstanding?”

Gwen rolled her eyes, tightening the cross of her arms.

“Thought so. You only care when it damages the family name. Worried about the opinions now?”

“Stop it! You don’t realize how crucial this is,” Leo retorted, frustration rising.

“My dad cut me off completely because of that blasted article!”

Gwen smiled, shaking her head.

“Oh, poor thing—your toys and allowance are gone, and now you’re angry?” Her sarcasm was potent, hiding a slight grin as she relished his dismay.

Leo’s face flushed with embarrassment. “So, will you help me or not!?”

“We’ll see if you are worth it,” Gwen retorted. “Work with me today, and I’ll consider if you’ve changed.”

Leo sighed, feeling trapped. “Fine…” he conceded, reluctantly.

By day’s end, Leo spent hours assisting Gwen in her volunteer efforts.

He distributed clothes, even offering comfort to some who seemed particularly down.

After clothes duty, Gwen led him to a soup kitchen where they prepared hot meals for the less fortunate.

Gwen handed him a potato to peel, and he fumbled, nearly cutting himself in the process.

Gwen was quietly impressed by his resolve—perhaps he had more to offer than arrogance.

At first, Leo’s irritation was apparent.

He was all stiffness, just going through the motions to convince his father and hopefully return to his comfortable life. But as time passed, his demeanor shifted.

He started greeting people warmly, and even occasionally took the lead, distributing clothes or offering help without prodding from Gwen.

Noticing this, Gwen approached him, a playful grin curving her lips.

“Well, look who’s here! Where’s the ‘real man’ who sneered yesterday?” she teased.

Leo laughed softly, shaking his head. “That guy was naive. Honestly, he was the lonely one,” he admitted, surprising himself with the honesty.

Gwen’s expression softened. “What do you mean?” she asked gently.

“I dunno… I’ve had everything on a silver platter all my life. Cars, fancy clothes, watches—anything. But today, helping people felt… fulfilling. It felt good.”

Gwen raised an eyebrow. “Is that genuine, or just to get in the good graces of the press?” she asked, her smile playing across her face.

Leo shook his head. “You don’t need to tell the newspaper…”

“What?” she queried.

“I mean it,” he continued. “Don’t tell them unless you believe it. My mess-ups aren’t on you. I think I can find what I need without dad’s money.”

Gwen’s grin widened. “You’re welcome here as long as you want. There’s room, and anyone willing to help will have a place.”

“Think they’ll accept me, after all I’ve said and done?”

“I’ll put in a good word,” Gwen winked.

Just then, a familiar Cadillac pulled up, and out stepped Richard, with Bob in tow.

“Leo! You’re still here? I’m surprised,” Richard said.

“Dad? Why are you here?” Leo asked, taken aback.

“I came to find you. You’ve met the conditions, so you can come home now.”

“What?” Leo looked to Gwen, puzzled.

Gwen chuckled.

“Made a call to the paper while you worked. They’ll retract the story and print it as a misunderstanding. They’ve got some photos of you helping, too,” she said with a twinkle in her eye.

“Thanks!” Leo remarked genuinely.

Richard smiled and asked, “So, need a lift back home?”

Leo glanced around, then returned Gwen’s gaze.

“I think I’ll stay a bit longer,” he replied thoughtfully.

Richard nodded, understanding, as he stepped back into the car with a proud smile.