Just hours after mutual friends introduced Toh Guoxiang, 26, to an assistant project manager, Toh attacked the man viciously, fracturing his jaw.
Due to his injuries, Mr Tan Chia How, 29, could not eat solid food for two months and lost 6kg.
Yesterday, Toh was sentenced to a year's jail for causing grievous hurt.
The court heard that Mr Tan had gone to the Pump Room at Clarke Quay with a friend, Ms Julie Lim Yi Chen, 37, at around 11.30pm on March 4 last year. While they were in the club, Ms Lim saw Ms Tia Lee Sun San, 24,with her friends, including Toh. Ms Lim invited Ms Lee's group to join them, and they agreed.
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Deputy Public Prosecutor Nicholas Lai said Mr Tan and Toh, who is self-employed, did not know each other prior to the meeting.
After leaving the club at 3.30am, Mr Tan and Ms Lim were walking to a taxi stand in River Valley Road when Toh suddenly attacked him.
Court papers did not mention the reason for the assault, but Toh had told investigators that he was tipsy when he committed the offence.
When Mr Tan fell to the ground, Toh forcefully kicked his face once, causing him to bleed profusely from his mouth. Toh's friends managed to stop the attack, and Toh later took a taxi home. Ms Lee and Ms Lim took Mr Tan to Mount Elizabeth Hospital, where he was found to have a fractured lower jaw.
DPP Lai said: "The victim has indicated that he has become more reserved and careful of his surroundings, and avoids going out to drink as he fears that the incident may happen again."
Toh also separately received a fine of $1,200 and a year's disqualification from driving, for driving a car without a licence and making use of the vehicle without the owner's consent.
The court heard that Toh drove his friend's older brother's car without his permission at around 12.20am on Oct 9 last year. His friend had momentarily left the vehicle with the key in the ignition.
Toh was driving along a carpark service road near Block 224, Jurong East Street 21, when he hit a parked car belonging to Mr Kang Soon Leong, 37, causing scratches and a dent on its front-left portion. Toh returned the car after leaving a note with his contact details on the windscreen of Mr Kang's vehicle.
Toh is now out on bail of $8,000 as he has to settle some personal matters. He will surrender himself to the State Courts next Wednesday.
For causing grievous hurt, he could have been jailed for up to 10 years, and fined or caned.