The Trial at the Chicago Apartment Gate

There are marriages that are blessed by love, and there are also love affairs that are hidden behind a series of harsh tests. On a gloomy afternoon in early autumn in Chicago, Mr. Richard Whitmore — the rich and powerful billionaire, founder of the Whitmore Properties real estate group — suddenly came up with an unexpected plan.

His son, Evan Whitmore — a gentle, intelligent but somewhat naive boy — met and fell in love with Lana Brooks, a beautiful young woman working in the media industry. Their relationship progressed rapidly, and after only a year, they were planning to get married. But deep down, Richard was always worried: did the girl really love Evan, or was she just infatuated with the family’s huge fortune?

A veteran of the business world, Richard understood that people’s hearts are unpredictable. He did not want his son to enter marriage only to be disillusioned. And so, a dramatic plan was quietly built.

He disguised himself as a security guard at a luxury apartment complex on the Chicago River — a place Lana frequented. His usual bespoke suit was replaced by a worn-out jacket, a low-slung wool hat, and a few fake wrinkles. He no longer had the authoritative look of a CEO, but now he looked like an old night guard, living on a meager salary.

Every morning, he stood by the guard station, wearing a “Night Security” badge, a broom in his hand, his eyes following the little movements of the girl he loved. At first, Lana seemed oblivious. But after a few days, the encounters began to reveal her true character.

One evening, Lana visited Evan, carrying a bag of pastries. As she passed through the gate, she saw Richard sitting on the porch, his face tired, his hands shaking as he held a glass of water. Instead of asking, Lana frowned:

“My car is already parked, but the parking lot looks like this, who would trust it, Uncle?”

His voice was cold, his gaze filled with contempt, as if his presence only made the place dirty. Richard nodded slightly, not answering, but recording his first impression.

In the following days, he saw Lana often passing by without saying hello. Once, he intentionally dropped his bunch of keys in front of him; Lana just glanced and walked away. On the contrary, when she met an acquaintance dressed elegantly, she always smiled brightly, friendly like a different person.

Once, Richard pretended to trip at the entrance, limping. Lana walked over, her high heels clicking. She glanced and then moved aside, frowning:

“Be careful when walking, don’t bother others.”

The cold words made Richard sigh. The image of the “good girl” that Evan had always praised gradually gave way to another face — cold, pragmatic.

However, Richard remained patient. He knew that to see their true nature, he had to give them the opportunity to choose in difficult circumstances. And the opportunity came sooner than he expected.

That night, the rain was pouring down Lake Michigan. Richard, in his drenched security uniform, leaned against a broomstick, watching the traffic. Lana got out of her small sedan, holding an umbrella, her face irritated by the traffic. Richard “accidentally” dropped a frayed wallet on the steps — the wallet he had prepared, containing some cash, a few old Walgreens receipts, and a picture of a child.

Lana saw it. She glanced around — no one noticed. She bent down to pick it up, flipped it over quickly, then closed it and stuffed it into her bag.

“Sir, remember to watch your car carefully when it rains tonight,” she smiled politely and walked away. That night, Richard checked the Lost & Found box in the security room. The wallet was gone. He told himself: one test doesn’t tell the whole story.

A few days later, Richard set up another scenario. In the morning, a delivery boy (new to the job) was blamed by the parking lot manager for denting the corner of his fender. He turned pale because the delivery was late. Lana walked by. “That security guard dented the resident’s car,” the manager pouted and spilled it. Richard was cleaning up the rainwater. Lana glanced at him, crossing her arms:
“Whoever dented it, pay for it. Don’t block the way.”
The delivery boy stammered; Lana turned away, not bothering to listen to the rest of the sentence. Richard had to speak up for him.

In the afternoon, Lana went to try on wedding dresses. Evan wanted a cozy party at his favorite restaurant, with most of the budget going to a scholarship fund — an idea he had been harboring for a long time. Lana nodded on the surface, but when she met the wedding planner, she changed her tune: suggesting a “Crystal Grand” package at a 5-star hotel with an LED stage, cold cannons, and a string quartet.

“This is my wedding,” Lana smiled, “I want everyone to know how much he appreciates me.” She lowered her voice to the planner: “If we get a good price, we can even cooperate on YouTube media, it’s a win-win situation.”
Richard — in the role of a guard called up to receive the goods — listened to the whole thing.

That night, he called Evan aside. Without rushing to expose him, he simply asked, “Do you think you two understand each other?” Evan replied firmly, “Lana is a character, a bit blunt, but kind.” Looking at his daughter’s bright eyes, Richard held back his feelings. But he knew he needed one last test — a touch strong enough to reveal the hidden thoughts in people’s hearts.

The next day, Richard leaked a controlled rumor through several middle managers: a Whitmore Properties riverside project was under scrutiny by the Illinois State Inspector, and cash flow might be tightened. The news reached Lana quickly. That night, she met Evan at a fancy coffee shop in the River North area…

Richard — in a security guard uniform — stood outside checking the car, silently testifying.

“Hey,” Lana lowered her voice, “I heard your father’s company had a problem?”
Evan smiled, saying it was just a routine checkup, the family would be fine.

Lana stirred her spoon, her eyes darkened: “If it’s really difficult, we can postpone the wedding. We’re still young.”
Evan was surprised: “I just want a simple wedding.”
Lana nodded, then asked as if unintentionally: “Simple is… to what extent? Where will we live? I don’t want to rent for long, and… I can’t stand the lack of things. I’m telling the truth.”
The words “I’m telling the truth” fell like a small stone but created a big wave in Evan’s heart.

The next day, outside the elevator lobby, Lana called her best friend — not knowing that Richard was standing half a step away:
“If that family takes it, we have to consider it. Getting married is for peace, not for working like a student.”
Her friend asked: “What about love?”
Lana laughed briefly: “Love needs money to feed.”

At noon, an old woman selling flowers was yelled at by the security guard. Richard intervened, asking her to stand by the row of trees to sell to residents. Lana had just stepped out of the elevator when the old woman offered to buy roses. She frowned:
“I don’t use cheap flowers.”
The old woman quickly stepped back, tripping over the edge of the flower pot; Richard caught her in time. Lana saw it but still walked straight: “This area must maintain its image.”

At this point, Richard no longer had any doubts. He decided to end the test. He invited Lana to Evan’s house this weekend to “discuss the wedding”. In his heart, he already had all the answers, but he wanted to hear her true nature speak in front of everyone.

On a weekend afternoon, the Whitmore family home in Lincoln Park welcomed guests with the smell of hot tea and yellow lights. Evan nervously adjusted his collar; Lana was radiant in a simple, elegant dress. She greeted the housekeeper politely, complimented the white orchid pot in the corner of the living room, as if she had never frowned at the old flower lady or the delivery boy.

Richard stepped out — no longer in his security uniform. He wore a light blue shirt, calm, and focused.

“Sit down,” he said to Evan, then turned to Lana: “Let me be frank.”
He placed the wallet on the table, its edges frayed and dry from the rain.

“Do you remember it?”
Lana’s face changed slightly and then she calmed down: “I… wanted to return it, but I was too busy…”
Richard looked straight at her: “You kept it for three days. There was a picture of a child in it. If it was lost, at least they would ask the security guard.”
Lana bit her lip: “I was wrong. But… it was just an old wallet. I didn’t mean to.”

Richard didn’t stop at the wallet. He recounted each event, each word: the delivery boy who was wrongly accused, the old flower seller who almost fell, the five-star hotel wedding package negotiation, the conversation at the coffee shop when the financial rumors spread. Each slice was placed on the wooden table.

“I was trapped,” Lana said, her voice hard.

“Call it a test,” Richard replied. “I want to know how you treat someone who can’t give you anything — like an old gatekeeper who gets wet in the rain — and how you will treat my son if one day he has nothing left to give.”

Lana looked down, honest but stubborn: “I was born into poverty. I swore I wouldn’t go back to that. I’m afraid of lack, afraid of being looked down upon. If one day Evan has no support, I… I don’t know if I can handle it. I don’t want to lie.”

Evan’s voice trembled: “Do you love me… or do you love the life I bring?”
Lana was silent for a long time, then spoke slowly: “At first, I was truly attracted to you because of your kindness. But the closer we got to getting married, the more I was obsessed with safety. I wasn’t as brave as you wanted.”

Richard looked at his son, his eyes filled with sadness. He turned to Lana:
“Thank you for your frankness. But marriage shouldn’t start out as a risky proposition. You have the right to choose safety, and I have the responsibility to protect my son.”

Lana stood up, bowed to the housekeeper, and looked at Evan one last time: “I’m sorry.” She left without drama or tears, leaving only the soft sound of the door closing.

The living room fell silent. Evan bowed his head, his hands clasped tightly. Richard put his hand on his son’s shoulder:
“I’m sorry for using this method. I was afraid you would be hurt, so I hurt you in another way.”

Evan smiled sadly: “At least, now I know where I stand.”

In the following days, the echoes of the story spread thinly like morning mist. Richard called the delivery boy, asked him questions, and then introduced him to work as a warehouse employee for a partner. The old woman selling flowers was allowed to stand on the sidewalk corner in front of the apartment complex during certain hours; he gave her an old bicycle that had been repaired. The worn-edge wallet—evidence of a test—was placed in a desk drawer, a reminder of the line between verification and suspicion.

As for Evan, he asked to be transferred to an affordable housing project—a plan that had been delayed because of low profits.

“I want to build houses that if one day I go broke, I can still afford to rent,” he said.

Richard nodded. In a rare moment, he felt himself letting go of the burden of a billionaire who always saw life as a series of risks.

As time passed, the story became a healing wound. No one denied that Lana had feelings. But her “true nature”—a fear of poverty as hard as stone and a pragmatism as cold as steel—had chosen a path for her. It’s not a crime, it’s just that the truth doesn’t match the love Evan wants.

Another afternoon, Chicago rained. Richard stood by the window, watching the drops of water tap against the glass. He remembered the janitor bending down to straighten a broken broom handle. He thought about what he had said: “Marriage is not a gamble.” And he knew that, if there was a next time, he would teach his son to recognize his companions more by listening than by their traps. Because in the end, what makes a life rich is kindness — not measured by a hastily picked wallet or a dazzling wedding, but only on rainy days when no one is looking.