“I Downloaded All The Dating Apps”: Ex-Convict-Turned-TikTok Star Simonboy On The First Thing He Did After His 2-Year Stay At A Halfway House

Local content creator Simon Khung, 36, better known as Simonboy, has been an open book on the internet since he started posting his videos about his life back in 2021.

Simon doesn’t shy away from talking about his 16-year drug habit and his time behind bars. After three stints in prison, two failed marriages, a failed suicide attempt, and two years spent in rehab at a halfway house, Simon has turned over a new leaf.

Crediting his new-found faith in Christianity and a strong support system for the change in his life, Simon now runs a clothing brand and heads a production company.

He boasts over 153K followers on TikTok, and promotes a drug-free lifestyle, in hopes to deter others from following his path.

Simon is the guest on the latest episode of R U Okay?, where he talks to Jean Danker and clinical psychologist Jeanie Chu about his struggles and his reformation journey.

After voluntarily checking himself in at halfway house The New Charis Mission in 2019, Simon got clean and left to start anew in 2021.

“When you came out, what was the first thing you did? Did you try to find a job?” asks a curious Jean.

Without missing a beat, Simon says: “First thing I [did when I] came out…I downloaded all the dating apps."

Jean and Jeanie burst into laughter as Simon continues: “Because after separation, being in and out of prison, and [going into the halfway house the moment I was released]… I lonely mah. I was a broken soul, so the first thing I did was to download all the apps. I downloaded Tinder, OKCupid, Coffee Meets Bagel, and Bumble.”

It only took Simon two dates, both with teachers, for him to meet his current girlfriend, who is known to his followers as Simongirl.

She played an instrumental part in helping Simon set up the social media presence he has today.

“When I met her, everybody knows, I was riding my bicycle doing food delivery. I only had S$50 in my bank, [but] she stuck with me. She’s working a very normal job, like normal salary, and she trusted in me,” he recalls.

They were only dating for “two to three months” before Simon started his social media career.

“I only promised her one thing. I said I would work really hard [at every] given opportunity,” he says.

She was crucial in the launching of his clothing brand, Chance. On top of unconditional support, she learnt to set up a website so he could have a platform to sell his tees. She also loaned him money to get started.

“When I asked to borrow money from her, she didn’t hesitate, she said yes. The next day she still reminded me, “If we [don’t] make it, it’s okay”. In other words, she was telling me if we don’t earn money, I don’t have to [return it to her], in a nice way lah. ‘Cos I’m a man mah, quite egoistic, so all along I don’t like to use her money even when we were very broke,” he says.

Jean was curious where Simongirl's trust came from.

“I think it’s built-up trust. Since the beginning, I always asked her to eat hawker food. We ate hawker food for many months. It was cai png every single day,” he says.

He goes on to explain that sometimes, when Simongirl got bored, she would suggest they eat something different, like Din Tai Fung. She would also offer to pay.

He said he would turn down her suggestion because he couldn’t let “a woman pay for his food”.

“Even when we’re broke, we’re still prideful. So she knows that I don’t spend her money,” he says.

Thankfully, his clothing brand took off, and he made “S$2K plus” during the first drop.

While still on the topic of his girlfriend, Simon recalls an incident from 2021, when he was involved in a high-profile traffic police case.

TL;DR: He was in the passenger seat of a car that reversed into a traffic police officer. The driver fled the scene, but was later caught. Simon, who was found standing outside the car, was arrested for allegedly using criminal force to deter a public servant from his duty, and suspected drug-related charges.

While the case was still undergoing investigation, Simon was released on bail. He later posted a TikTok stating that his urine test was negative, and denied the charges named against him.

“My phone was under investigation, so I didn’t have a phone and I had already started my TikTok journey. When [my girlfriend] bailed me out of the police station I asked her 'Eh what to do now?'. It was the first [time] I had something to look forward to in my life — my content. She said 'It’s okay, we go and buy a phone'. She signed off on a phone for me,” says Simon.

He admits he was “immature” during his previous two marriages, but he now knows relationships aren’t simple, and that “a real relationship doesn’t work just because you love each other”.

“There are a lot of things to consider. Finance, plans, goals, mindset, and direction in life,” he says, adding that he’s “very careful” this time round.

During the early days of their relationship, he admits there was “a lot of temptation for drugs”.

However, with his wish to have a healthy family, and Simongirl’s positive presence in his life, Simon has managed to keep himself anchored, without falling back into his old habits.

He says: “I told myself, ‘I have her already, I cannot disappoint her’. She really trusts me. She knows my background, [but] she still sticks with me.”

Catch all 3 seasons of R U Okay? on meWATCH here. You can also listen to the podcast on Spotify and meLISTEN.