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.
"After a while, I woke up (on a bed in the flat). I was bleeding down there even though I was not having my period at the time. I knew that something horrible had taken place.
"I felt very dirty. I didn't dare tell my parents because I felt that they trusted him very much.
"I felt so cheated. I also knew that if I were to go to the doctor, they might want to see my parents. That actually scared me," she said.
She quickly left the flat and for the next few days, she felt pain in her lower abdomen.
Soon after this, Ms Linda said that Alex tried to meet her more regularly.
He would also visit her flat, telling her parents that he wanted to talk to her.
"I told my parents I didn't want to talk to him. They asked me "What's wrong with you?'. I said I just didn't feel comfortable (around him) any more," she said.
Noticing she was avoiding him, Ms Linda alleged he threatened her, claiming he had photographs and videos of his sexual assault and would show them to others.
But she stood firm and continued avoiding him.
They were no longer in touch after 1996.
She said she decided to suffer in silence but the horrible memory came back to haunt her last year after she read the news report about Alex's court case, where he was convicted of sexually abusing a teenager.
He was later jailed and caned.
So why did it take her 18 years to make a police report?
Ms Linda said: "I decided that enough was enough. I want justice to be done as a form of closure for me."
She broke down in tears and later phoned one of her closest friends, Mr Peter (not his real name), 51, for advice.
The financial consultant, who has known her for eight years, told TNP that she sounded distraught.
He was shocked when he found out that she had been a victim of rape.
Said Mr Peter: "She always appears cheerful. I was speechless. I didn't know how to console her. I encouraged her to go the police to get it out of the way."
She made a police report in July last year.
It was one of the 121 rape reports made last year.
Even though many years have passed since the incident, Ms Linda still finds it difficult to trust other men.
She said: "I was once married but we divorced four years later. We didn't have any children as I didn't allow my husband to touch me. I'm now very paranoid about relationships.
"I can't sleep easily. I keep having nightmares."
Sexual Assault Befrienders Service (Sabs): 6779-0282
Samaritans of Singapore (24 hours): 1800-221-4444
Singapore Association for Mental Health: 1800-283-7019
Care Corner Mandarin Counselling Centre: 1800-353-5800
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