Skip to main content
Best News Website or Mobile Service
WAN-IFRA Digital Media Awards Worldwide
Best News Website or Mobile Service
Digital Media Awards Worldwide
Hamburger Menu



CNA Insider

He's 35 and homeless: Eight years of destitute living

Born to a well-off family, he made a bad choice that led down a path of regrets. Now every day is a struggle to climb back out of his destitute state - if only the past didn’t get in the way.

09:23 Min
"Make an effort to find out more, before you crucify us with your prejudice." Ben, 35, has been homeless for eight years, and has been striving to overcome the ghosts of his past to get out of his state of destitution. Read more of his story.

SINGAPORE: The first time I meet Ben and we shake hands, I am immediately assailed by the scent of cologne. Over lunch, the intense fragrance almost overpowers the aroma of roasted coffee beans.

“Actually,” he says casually as he twirls his straw, “I haven’t bathed for a week.”

Oh, I think, as I give him my best unfazed nod and an “I see”.

He peers at me for a good three seconds, then breaks into a huge smile. “Wah, your poker face is damn good. Usually people will be grossed out.

“But I’m joking lah. I did shower,” he adds gleefully. “You actually believed that?”

One might easily have. Ben - not his real name, of course - has been talking about his experiences as a destitute younger Singaporean. One who’s been sleeping in public places for these last eight years. Not that you would think “homeless” just looking at him.

Neatly groomed, looking younger than his 35 years, and togged out in a black Adidas polo shirt, he tells us how he wanders into the department stores to use the cologne testers when the staff are distracted.

“Not bad right, you get to try a different brand everyday,” he jokes. “You wouldn’t want to smell or look like a stray dog, right?”

He wanders into shopping malls and looks no different from any of the shoppers.

Like the majority of those who are homeless, Ben is a loner by nature. Unlike others, he agreed to share his story with us - after being introduced by the group The Streets of Singapore - because he thinks Singaporeans should know what it really is to be destitute, and how some of their prejudices and stereotypes are misplaced. 

One of those stereotypes is that the homeless are dirty, elderly, aimless vagrants. A just-released street survey  - the first of its kind here - found that, in fact, about two in five homeless people are under the age of 50. Some three in five hold a job, in many cases a full-time one. And about the same proportion have been sleeping in public places for a year or more - like Ben.

Read: Homeless stereotypes busted

But the first eight years of Ben’s life couldn’t have been more different from the last eight.

Born into a middle-upper class family and growing up in a landed private home he was not what you would think of as a candidate for homelessness.

An only child, he did relatively well in school - an “elite” one, he said. They went on family holidays to America and Europe.

Then everything changed when he was nine years old.


Though his material needs were well-provided for, Ben described his family as “severely dysfunctional” and his childhood as “turbulent”.

His mother, who was mentally ill, jumped to her death when she was 41. It hit Ben hard.

“My father was hardly around because he was busy working. After my mum passed away, my academic performance started to plummet. Usually she would be the one to guide me through my studies… so I lost interest,” he said.

Becoming more introverted, he also became a target for bullies in school and was picked on almost every day.

While Ben struggled to work through his grief, his dad began building a new family.

“My father’s main priority was to get things back to normal, so he eventually remarried. He just pulled me aside and said: ‘You know what, I’m going to marry and this is your new mother.’ And he had a new child.

So I got left behind. A lot of things were kind of disasters waiting to happen.

Unable to get along with his father and stepmother, whom he described as “domineering and controlling”, he ran away from home and stopped going to school after his O levels.

It came to a point when his funds ran out. But he refused to go home. “I knew I was going to be punished (if I did),” he said.

Running away from home was the next step in his downward spiral.

One night at 2am, Ben found himself walking along a row of bungalows, tired and hungry. His TransitLink card had run out of value as well. Desperate, he decided to break into a house and, by a stroke of luck, the door had been left unlocked. Inside, he found a wallet lying invitingly in the living room.

“I didn’t even have to go into a bedroom, you know? It was just there.”

That night, he “swiped” S$200 and an American Express card. The cash was soon exhausted - and, emboldened by his clean getaway, he decided to strike again.

But this time, he did not realise the maid was still awake, and she had spotted him climbing over the fence. “When I was snooping around, the police was already on their way,” he said.

“They arrested me. That was probably the beginning of the end of my life.”


His first night at the police station lock-up was an ominous indication of what was to come in prison. He claimed he was assaulted and nearly raped by a fellow detainee.

In jail, he said, it was survival of the fittest. “You’ve got the gangsters. Thieves. And the sexual offenders. It was a very harsh environment. Needless to say, it was a living hell.”

At the age of 18, he was sentenced to two years in jail. He appealed for a probationary sentence - a year of probation and release on good behaviour - but this was denied.

“So basically, I was sent to jail for two years for stealing S$200... I was a first-time offender, unlike all these people active in secret societies. In my mind, I was cursing and swearing.”

In prison, Ben kept his head down and tried to retake his O levels.

Ben decided to keep his head down and retake his O-levels. To take the exams, he had to be transferred to another prison - but in his psychiatric assessment, he was diagnosed with depression and anxiety. “My (transfer) application was rejected,” he said.

His second attempt to request for a transfer was approved after he managed to get the support of another prison warden. Yet, Ben did not exactly get what he wanted - he was assigned to take the N-levels instead.

Nevertheless, he served his time and got out with an N-levels certificate. He was 20 years old when he returned to the world.


Having missed two years of his life, Ben found himself feeling left behind yet again.

“The world waits for no one. Basically I had been in a cage. When I came out it was like ... all the greenery. Everyone had a cellphone now. Before I went in, I don’t remember having a cellphone,” he said.

I felt like a dinosaur trying to read Latin.

Ben had another one and a half years of electronic monitoring to complete, during which he had to remain in his father’s home. Two months after this was over, he got the freedom he’d yearned for.

“My dad told me to leave,” Ben recalled. “He said, you’re 22. You’re an adult, you can take care of yourself.”

“To be honest, I anticipated it. It didn’t surprise me at all. Of course I said okay.” That was the last time he ever spoke to or saw his father.

For the first six years or so, he bunked in with a friend and then rented his own room.

For the first few months, he crashed at a friend’s place. He managed to secure jobs in clerical work, sales and telemarketing through friends’ recommendations. “I was still able to make a living,” he said.

Eventually he had to rent a room of his own because his friend’s parents were not happy. Fortunately in 2003, room rentals hadn’t yet escalated, so he could afford to rent a room for S$200 to S$300 a month. He continued renting for six years.

But things changed when he enlisted for national service. His allowance was not enough to cover the increasing rent.

“You were supposed to book out of camp every day and go home, but I did not have a home,” he said. “That’s when I officially became a destitute.”

He was 28 years old.


It’s 10pm, and we enter a fast-food joint in the heart of the city where Ben sleeps every night. It’s packed with students studying and supper groups. The atmosphere is full of bubbly mirth.

Ben makes his way to his usual spot, an obscure corner behind a wall with a long table and cushioned seats. Unfortunately, it’s occupied by a boisterous group who look like they’ve just started eating.

“Okay… we need to look elsewhere for tonight,” Ben says with resignation, as he makes a u-turn.

As soon as we find another cushioned seat against a wall, he takes out his packet of Dettol wet wipes to give the tables and seats a good wipe-down.  “You wouldn’t want to put your head where someone else put their feet, right?” he says.

He’s not the only destitute individual spending the night at this outlet. A quick head count at 10.30pm reveals there are already seven of them.

“I know the faces, but we mostly just keep to ourselves. People get territorial, everyone has their designated sleeping spot. If you sleep in my spot, where am I going to sleep? Disputes like that do happen,” Ben reveals.

“In fact the lady who usually sleeps here saw us just now … She made a face and left.”

It is hard to believe how Ben will get any rest tonight. The music in this outlet plays 24 hours, and it’s anybody’s guess when the crowd will disperse - especially on a weekend.

The one thing I miss the most is privacy, having your personal space.

"When you are in public 24/7, it is very hard to get peace of mind. You feel like you are being scrutinised every single moment," he said.

“Even animals have their own nests. Humans need their own home too. This is not home - it’s just a resting spot.”

The homeless in Singapore most commonly roost at night in public parks, shopping malls, HDB blocks and town centres, the street survey found.

In the eight years that he has been homeless, Ben has slept at various places which operate for 24 hours. They range from Lan shops to accident & emergency waiting areas at hospitals. However, Ben says he has fewer places to sleep at these days.

“Since last year, a lot of Lan shops have closed down because everyone uses smartphones these days.”


Police spot-checks, which take place especially in spots known for criminal activity, can be disruptive to a good rest - more so if you have a criminal record, Ben says.

“All they have to do is read out your IC number, relay it to HQ on their walkie-talkies, and they’ll know if you have a criminal record. They even know which year you did it, what is the nature of your offence.

“Once they know you have a criminal record, they’ll talk to you like you’re some kind of crook and then they’ll search your bag.”

Ben, who also has obsessive compulsive disorder, gets particularly annoyed at such spot-checks. All his belongings are kept in a certain order.

“They take everything out. You think they’re going to put everything back in order? For them it is part of their job, but they are also screwing up my life.”

His medical documents, contact lenses, toothbrush,wet wipes, and a spare set of clothes are some of the bare essentials he carries around.


He can get prickly, because pride and dignity are things that he clings to.

“I ask you, when you first saw me, did I look like a typical destitute person to you?” he asks. I smile and shake my head, which seems to satisfy him.

While it’s not uncommon to see some homeless individuals toting as many as six or seven bags containing all their worldly possessions, Ben has only two bags with him at all times - a fanny pack on his hip, and a discreet sling bag.

The fanny pack holds his valuables, like his handphone and wallet. The sling bag contains his medical documents, contact lenses, toothbrush, toothpaste, wet wipes, disposable underwear and a spare set of clothes that he uses as a pillow when he sleeps.

Just the bare essentials, he says.

All that Ben needs on most days fits into this sling bag and this fanny pack.

He has other belongings, but they’re kept in a friend’s storeroom. He goes back only when he needs to, or once a month to get a change of clothes.

“It is not convenient to carry too much because I’m constantly moving from one place to another. I see a lot of these destitute persons carry huge bags and luggage. If you do that once in a while, you could pass off as a tourist. But if you’re doing it every day, then people would know.”

Appearance is everything to Ben. 

Some people don’t give a damn that people know they’re homeless, but for me, it is easier when people are not aware.

"For example, many destitute people can’t enter hotels because they look really scruffy. But I can enter most places because I bother to maintain my personal hygiene.”

Every morning, he takes an hour to get ready at a handicap toilet in a library. Occasionally, he takes a bath at a hotel’s common shower rooms - even though it is not allowed. While there, he also washes his clothes and dries them with a hairdryer, and puts them on again immediately.

But there are moments when it helps to look destitute, he says candidly - such as when you need help or when asking for a meal.

“Other than that, I don’t go around advertising that I am. You have to be smart and be like a chameleon.”

Blow-drying his clothes straight after he washes them in the shower.


For the last eight months, Ben has been working as a banquet waiter, making about S$500 to S$800 a month.

He does not enjoy the work, but is doing it to make ends meet. His income largely depends on whether he is assigned jobs by agencies and the hourly rate he is paid.

“You know Maslow's pyramid right? To be able to proceed to higher levels, you need to satisfy certain lower needs first. You have to get a stable job first, then you can think about more lofty aspirations,” he says.

Last year, he completed a diploma course in tourism at the Tourism Management Institute Singapore, in the hope that it would be “leverage” for a better job. “Instead of doing saikang (shit work) for the rest of my life, you know? I don’t think anyone wants to live like that, right.”

He’d worked at several cleaning jobs like dishwashing in order to save up more than S$2,000 for the course fee (70 per cent of which was subsidised by Workforce Singapore). Saving up gave him a sense of direction, he said, and once he’d accumulated enough, he pumped everything into the course.

But the returns have been disappointing. 

“It’s probably more of a placebo effect. You feel more confident: At least you got a diploma. But so far, I  haven’t been successful in my efforts. You’re not going to land a cushy job just because you got yourself a diploma. There are so many people with degrees these days.

“So I’m back to square one.”

Ben attributes his difficulty in finding a better job to his criminal record as well. Many doors have been closed - for example, he can never apply for security-related jobs. He cannot drive for Uber or Grab either, he said.

I ask if he ever regrets his past actions.

“Every day,” he says, voice tinged with unmistakable remorse.  “A criminal record is permanent. Nothing you do is going to erase that.

“You’re going to live with that for the rest of your life.”

WATCH: The homeless life (9:23)


It’s lunch time and we’ve picked an upmarket food court, which I soon regret because I worry it might be too expensive for Ben. But after ten minutes, he returns to the table with a large portion of Japanese omelette curry rice, with an extra topping of beef.

“This is to show that homeless people can pay for their own meals,” he says pointedly as he sets his plate down.

He is keenly aware of the stereotypes attached to the label “homeless” - such as someone who’s lazy or incompetent. Who doesn’t make any effort to improve oneself or get out of the situation. Someone who just wants to rely on the welfare of others.

But, he counters: “It is easy to criticise others when you are not in the predicament yourself.

“Some of us might have been able to surmount obstacles and move on. But not everyone can do that ... or has the strength or resources to do that.”

Right now, he just wants his own accommodation. When he turned 35 in June, he became eligible for a public rental flat under the Joint Singles Scheme. He has managed to secure one and is due to move in in December this year.

But he’s not particularly optimistic about the prospect.

“You have to live with another person. Most people can’t even get along with their family members, let alone with a total stranger.

“There are a lot of destitute people who are in that scheme - they just sleep outside because they can’t get along with their housemates.”

At 35, he's managed to secure a rental flat under the Joint Singles Scheme.

Like most people, Ben craves to see the world. He wants to share his life with someone. He even dreams of owning a wolf-dog someday. But he is doubtful of ever achieving these things.

"I am working on it. Because if you can’t, then it’s just a stupid dream… I am trying to make an effort to come out of this. But it’s not that easy or straightforward a journey.

Compared to the average person, I have more disadvantages. But then instead of complaining about it, you have to fight and make something of your life.

“You have to make it count,” he says.

It’s now 4am, and as we take our leave, the fast food restaurant is still abuzz with activity. Ben beds down for the night - what’s left of it - while a group of teenagers sit right next to him, raving about a new mobile game. When was the last time, he experienced complete silence, I wonder?

But long experience has made him oblivious to them, and to the fellow destitute man whose head lies just inches from his. We leave Ben stretched out on the narrow seats, on which he’ll turn occasionally as he dreams.

Perhaps of wolf-dogs. Perhaps of a future he dares not quite fully hope for yet.

Read here for more about homeless persons in Singapore.

Source: CNA/yv


Also worth reading