She looked up to her brothers' friend and treated him like family.
But Ms Linda (not her real name), 35, claimed the man raped her in 1995, robbing her of her virginity.
For 18 years, she kept this a secret until she read about a rape case in the papers and realised the rapist was the same man who had allegedly violated her.
Only then did she find the courage to make a police report.
The police confirmed that the report was made last year and that investigations are on.
The businesswoman told The New Paper she was only 15 years old when she was raped and did not know what to do after the incident.
She said the rapist, Alex (not his real name), was close to her family members, including her parents, at that time.
Ms Linda said she first met Alex in 1988 when she was living with her family in the northern part of Singapore.
He was a close friend of her two elder brothers and used to visit their flat regularly.
"He seemed to be a very nice man before the incident," she said. "He used to advise me and made sure I came home on time (after school)."
But seven years later in 1995, Alex, then 23, invited her to watch a movie at a mutual friend's flat in the same neighbourhood.
They were the only ones there when they reached the unit.
Ms Linda alleged that he handed her a glass of orange juice and she felt tipsy after drinking it.
She said she lost consciousness.