One spoke perfect English tinged with an American accent. The other could manage only smatterings of the language, at best.
Yet Mr Teng Cher Meng, a contractor, felt a strange affinity with his client, Ms Autumn Radtke, 28.
At one point, the CEO of bitcoin company First Meta even hugged Mr Teng, 58, for 10 minutes, crying so hard that his shirt was soaked.
A day later, she leapt to her death.
This was heard in court yesterday, during the coroner's inquiry into Ms Radtke's death in February.
Although Mr Teng did not fully understand then why Ms Radtke was so upset, he did not expect her to end her life.
Speaking to The New Paper in Mandarin yesterday, he said: "I didn't believe it when I first heard about her death. Even though I didn't know her for long, I was so sad, I cried."
The contractor first met Ms Radtke, a tenant at a shophouse along Everton Road, two months before her death.
She had called him to fix some defects and do renovation work in the house, which she also used as an office for First Meta.
Said Mr Teng: "She was a very nice and cheerful person. She would often offer to buy lunch for us."
He added that Ms Radtke, who was fond of having house parties, would often invite him.
He never joined any of them as he did not like such social events, especially when he knew only simple English.
Indeed, language was a barrier between him and Ms Radtke initially.
"My English is very chapalang (Singlish for random mix) and I often had to add some gestures to convey what I mean.
"Strangely, she began to understand what I meant after a week," he said.
Mr Teng recalled a time when she had asked him to help look for her missing Persian cat.
They never found her cat, but the incident strengthened the bond between the two.
On Feb 24, two days before Ms Radtke's death, Mr Teng recalled the American's unusual behaviour.
"From 9am to 3pm, I watched her pacing up and down the house, talking on the phone loudly.
"She looked so agitated. She usually wasn't like that," he said.
The next day, she suddenly burst into tears in front of him.
HAD NOT SLEPT
"I was smoking at the door. She suddenly came out and told me she had not slept for a night, then hugged me and burst into tears.
"I couldn't really understand her, but I heard the words 'America' and 'money not here'.
"I concluded it was some kind of financial difficulty, and that she was homesick," he said.
He did not probe further as he did not want to seem nosey.
Instead, Mr Teng offered her a cigarette and the two of them smoked together silently. That was the last time he saw her.
He found out about her death hours after Ms Radtke's body was found on the roof of a rubbish collection point at Block 8, Cantonment Close.
It was revealed during the coroner's inquiry that the she had jumped from the 16th storey of that block. According to her friends, she was fond of the number 16 as she was born on Oct 16.
Seven months have passed since Ms Radtke's death, but Mr Teng still wonders why she took the path of no return.
"She was so young.
"She died too early," he said of his client, whom he had grown to regard as a friend.
She was troubled by money woes
Ms Radtke was the CEO of bitcoin company First Meta, a Singapore-based virtual currency exchange company.
First Meta allows users to buy and sell virtual currencies, including digital currency bitcoin, for real money.
Witnesses' accounts revealed that the American citizen, who became the company's CEO in 2011, was troubled by the firm's losses.
On Valentine's Day, she had confided in her boyfriend, Mr Daniel Pohlod, 30, about her financial woes.
She earned about $7,000 a month, and more than half of it went to the shophouse rent, she had said.
Mr Pohlod, who was at the inquiry yesterday, declined to speak to the media.
In the weeks leading up to her death, Ms Autumn Radtke, 28, was preoccupied with thoughts of ending her life.
She broached the topic of suicide when she talked to her close friend, bitcoin company GoCoin CEO Steve Beauregard.
"Have you ever considered ending your life?" she had asked him, a coroner's enquiry was told yesterday. Five days before she died, she saw a doctor for her poor sleep and loss of appetite, and was given medication for anxiety and depression.
A medical report said the prescribed drugs did not increase any suicidal risk.
A computer forensic examination of her laptop revealed that Ms Radtke had visited suicide-related websites 46 times two days before she died.
Then, on Feb 25, she visited an HDB block at Cantonment Close two times. The next day, she went there two more times, jumping from the 16th storey on her last visit. Her body was found on the roof of the block's rubbish collection point.
No cocaine was found in her urine sample, although a piece of paper stained with the drug was found in her pocket when she died.
State Coroner Janet Wang said Ms Radtke was determined to end her life, and had made "concerted efforts" to do so.
"Regrettably, this could have been forestalled with timely intervention and support, given that the deceased had demonstrated some measure of distress to the people known to her before her demise," she said.