The self-professed shy guy stepped into the spotlight when he uploaded a video of himself on YouTube talking about wanting to find a girlfriend by Christmas.
Mr Terry Chia has been single all his life because he finds it difficult to speak to women one-on-one.
But on Tuesday night, he went for the first date of his life at The Halia at Raffles Hotel.
That afternoon, the 24-year-old assistant producer said: "I'm anxious and nervous. I'm leaving my workplace early to go home and shower first."
On the train, Mr Chia listened to music to steel his nerves.
He then took deep breaths in the toilet to calm down.
For his date, he brought a paper bag containing a gift - a nicely-packaged bar of soap.
Mr Chia said: "I want to be more courageous. I'm actually a very introverted guy and don't want to talk to women, but I'll just do it."
Before the date, he received an image makeover and dating tips from dating company Lunch Actually.
Its coaching director, Mr Kydon Tay, said: "The day before the date, I brought Terry out to talk to women (in public). He realised that women are human too and it's not scary to just talk to them.
"After just 11⁄2 hours, he was able to go up to a girl to talk to her about her interests. Can you imagine a guy who's never been on a date before improve at this speed?
"His misconception was that women are difficult to talk to and he didn't know what to say."
Mr Chia found his date with help from radio station Kiss92.