Homeless Billionaire: Looking for Love

Christopher looked down at his outfit and shook his head in dismay.

It was ironic. As the son of a billionaire, he could've snapped his fingers and gotten clothes ordered from the finest boutiques in New York, Paris, or Milan. Or he could've had an army of tailors take his measurements and create any garment that the mind could imagine.

But to pass as a homeless person? Ah, that took a little more creativity. At first, he'd sent his butler to the local thrift stores, hoping to find something suitable there. But to his dismay, all the clothes had been washed, and anything too raggedy or threadbare had been discarded before it hit the sales floor.

Nonetheless, Christopher had ordered his butler to heap mud onto the items from the thrift store, followed by a good soaking in some beer as well as a mix of random condiments from the pantry. But that had just made the clothes sopping wet and completely unsuitable to wear.

In the end, money solved the problem - as it usually did - when Christopher had his butler drive around town until they found some genuine homeless people and bought the shirt right off their backs, so to speak.

And now, here he was, dressed in pants that were two sizes too big and reeking of a sour odor that he preferred not to inquire too closely about as well as a stained sweatshirt that said "Harvard Law," which was pretty ironic since his father had an annex named after him at Harvard following a sizable donation to his alma mater.

To complete the look, Christopher was wearing some ratty old Converse All-Star shoes and mismatched socks, with a faded Oakville Stampeders ball cap on his head to cover up his thick hair.

After taking a deep breath to steady his nerves, Christopher walked up to the door of the homeless shelter and pulled it open.

Inside, to his surprise, it was almost like a waiting room at the airport, except there were no concierge staff inquiring if he wanted a hot towel, of course. Instead, there was a row of cheap plastic chairs next to a reception desk, and the place looked quite cheerful and clean.

"Hi there," said the middle-aged woman behind the desk, spotting him immediately.

"Hey," said Christopher, making sure not to smile. He'd forgotten to do anything to darken his teeth, and he didn't want anyone to notice the anomaly.

"Welcome to H4H," said the woman, giving him a warm smile. "My name is Bianca. Are you looking for some help?"

"Um, uh, I heard you have a place I could stay," said Christopher, adding, "You know, to get out of the weather."

"Why yes, we do operate a shelter," said Bianca. "And you're just in luck! A bed just opened up. Come on over and let me get you situated."

Delighted to have passed the first hurdle, Christopher followed Bianca over to the receptionist desk. What followed was a lengthy questionnaire, which Christopher hadn't expected.

The good news was that Bianca assumed he couldn't read, so she did all the writing. The bad news was that he hadn't fully prepared his backstory, so he had to wing it on a few items, including his history with "substances."

"Um, yeah, it's the drink, you see," said Christopher, his pulse racing. "I just can't put down the bottle."

"Mm-hmm," said Bianca, writing everything down. "That's okay. A lot of our residents struggle with substance abuse. Are you going to AA meetings?"

"Hm," said Christopher, trying to decide which answer would sound more appealing. "Yeah, yeah, AA. Good people there. Very helpful."

"Excellent," said Bianca, nodding. "Well, we hold AA meetings here twice a week at the center. If you want to go more frequently, we post a list of nearby meetings in the cafeteria."

"Ah, cool, yes," said Christopher, wishing he could scratch his scalp because the ballcap he was wearing was making his head itch horribly.

"All right, I think that's about it," said Bianca, impossibly cheerful despite the stink cloud he was putting off. "Do you have any things?"

"Things?" said Christopher, taken aback by the question.

"Yeah, your personal possessions," said Bianca. "Each resident gets their own cubby here, and you get to hold the key. Staff do not have access to them, so your things will be safe."

"Oh, right, my things. Yeah, yeah," said Christopher. "I, uh, left them with a friend."

"No problem," said Bianca, unfazed. "You can go and get them later. Now follow me and I'll show you where you'll be sleeping."

"Ah, thank you very much," said Christopher, relieved that the questionnaire portion was over.

He followed Bianca down a hallway, and then they entered a large space that looked like it might've been a school gymnasium at one point. The floor was subdivided into grids using colored tape, and inside each square was an army cot as well as a small dresser near the head of the bed.

"Okay, you're number 52," said Bianca. "Remember that number, okay? I know some residents don't like the numbering system, but it helps ensure that we provide everyone with an equitable share of the resources."

"Right, sure, sure," said Christopher.

Looking down at the spare army cot, he could scarcely believe he was actually going through with this. But after months of searching for his brother to no avail, there was no other option but to go undercover.

Somehow, his brother had managed to stay off the radar, eluding the finest private investigators that money could buy. The only tip the family had received about his whereabouts was an unconfirmed report that he'd been spotted panhandling in a park downtown.

All attempts to question the local homeless population had turned up empty handed, so now Christopher was here, hoping to maybe find some clue as to what had happened to his brother and why he had dropped out of society.

"Okay, last question and then I'll go get your bedding," said Bianca. "What name would you like to go by?"

"Name?" said Christopher, dumbfounded. It was only then that he realized that she had yet to ask him for his name, which was usually the first thing that everyone wanted to know.

"Relax, we're not the government," said Bianca with a little chuckle. "If you want to go by 'Spider' or 'Squirrel,' that's perfectly fine by us."

"Ah," said Christopher. "Um, you can call me Christopher."

"Well, it's very nice to meet you, Christopher," said Bianca, extending her hand. "And welcome to 4H4. We're glad to have you here."

"Um, thanks," said Christopher, feeling his cheeks go warm as he shook her hand.

He'd never shaken hands with a homeless person before, and he could scarcely imagine why anyone would want to. They were either crazy or out of their minds with drugs.

Most of the time, he didn't even want to look them in the eye. And yet here was this perfectly nice woman shaking his hand and treating him like a normal human being. It was such an unexpected move that it left him feeling quite dumbfounded as she scurried off to go get his bedding.

Everything had seemed so simple when he'd first planned this operation, but now, he was beginning to think that maybe he'd badly misjudged the situation.