This opening of  Chapter 13, “Nanyang Family,” sets the stage for the conflicts that will eventually develop between an older generation’s idea of how a  new high-tech communication paradise should be constructed in Singapore and a younger generation’s dreams — particularly those of a young gay Singaporean who begins simply as a blogger, “S2.”

Centuries before the British had taken the island that would be Singapore, the land had already been used for monitoring cargos moving through the narrow strait of ocean between the Malay Peninsula and the island of Sumatra. That slender strait linked the Indian and Pacific Oceans and with them the rich lands of India and China. What would be Singapore was little more than a pebble, just forty-two kilometers long and twenty-three wide, but it was a strategic pearl. Like Bali, the island had alluring beaches and green hillsides, but after the British converted it to a free trade zone in 1819 Singapore’s image would not focus on beauty but on business. Its culture would become a stew of the dominant economic forces in the strait: the British, the Chinese, the Hindu, and the Islamic. Its population would rise to more than 200,000 by the end of the nineteenth century and then nearly double as Edward VII’s reign ended and World War I neared.

During those decades, the British reconfigured the island from its role as a tidy spice cabinet for trading nutmeg, cinnamon and cloves into the world’s largest warehouse for sorting and exporting rubber, transported from the plantations being created in Malaya. The rule became that a national metamorphosis would have to occur every few decades in order to keep up with the trading demands.

Along the way, the incoming male labor force added a second reputation to the island. By the 1920s, when Walter Spies sailed for Southeast Asia on the Hamburg, Singapore had become a booming brothel for Asian women who thought they were coming for jobs but instead ended up in the sex trade, either deliberately trafficked or slipping into it as a matter of either temporary or permanent survival.

Their children were sometimes pressed into those trades offered by the brothels, the girls following in their mother’s footsteps, the boys marketing in secret brotherhoods to find additional profit. These children, along with the sons and daughters from marriages among Chinese laborers, had no schooling and, being poor, made weak candidates for the elite British school system set up by the man who had negotiated British control, Sir Thomas Raffles.

That was where Singapore’s Nanyang Primary School came in. In 1917, the school was created as a piece of the Nanyang Girls’ School to help break the cycle of illiteracy and poverty for the children it could gather into its classrooms. It was a private school, not government, and it was specifically for the Chinese. For decades, Mandarin would be the language of instruction. The first year that Nanyang opened in a rented shop house next to a Chinese movie theater, one hundred children came.

Over the decades, the Nanyang School’s fortunes would follow the path of the city growing around it.  In 1927, the school’s faculty moved to a section of Singapore called Bukit Timah, along the slopes of what was the island’s highest hill. In World War II, the British used the school as a field office until the Japanese chased them out and destroyed Nanyang. After the war, Chinese alumni, grateful for how the school had helped them, rebuilt it. As the island’s economy once again transformed — this time from rubber transport to manufacturing — Bukit Timah became a center for industry and Nanyang’s children changed into the sons and daughters of blue-collar factory workers.

The school became its own metaphor for Singapore. With education, Nanyang helped the children and grandchildren of the original migrant Chinese workers move toward middle and even upper class economic paradise. These days, Nanyang maintains a website where it flashes its values in both Mandarin and English characters: “Diligence, Prudence, Respectability, Simplicity.” The school song, sung in Mandarin, takes only one minute to assure seven-to-twelve-year-olds that “Nanyang gathers glory,” and “Nanyang produces distinguished students” and “We become complete by working hard together pursuing glory, building up our country and developing our mind and body.”

The Nanyang School also imposed a dress code of gender propriety. Girls cropped their hair above their shoulders and wore white box-pleated skirts stretching below the knees. Boys wore white shirts and khaki shorts.

By the late 1950s, when the island’s most prominent married couple, Prime Minister Lee Kuan Yew and his wife Kwa Geok Choo, were deciding where to send their first-born son to primary school, Nanyang seemed a logical choice. Both parents had taken education

very seriously. Lee Kuan Yew’s father had gained a British education in the colony while Lee Kuan Yew himself had attended the Telok Kurau English School in the years preceding World War II. Telok Kurau sat on a vast coconut plantation distant from Singapore’s noisy wharves and brothels, and it was a school where a photograph from the time showed Chinese schoolboys dressed in crisp white shirts and shorts playing pianos and violins with the coconut trees forming a backdrop.  From Telok Kurau, Lee Kuan Yew had won a scholarship as one of the island’s brightest students and had then graduated from Singapore’s leading British high school, the Raffles Institution, begun by the city’s colonial founder himself, Sir Thomas. He had then traveled from the edge of the British Empire to its center and had graduated from Cambridge University as a lawyer. His wife had excelled too. She had taken a spot as the only girl at the all-boys Raffles in a special class set up for students hoping for a Queen’s Scholarship to study at either Oxford or Cambridge. Winning, she too had moved from the periphery of the Empire to its center and, as would her husband, had graduated from Cambridge Law. Back in Singapore, they along with Lee Kuan Yew’s brother had formed the law firm of Lee and Lee.

Their first son, Lee Hsien Loong, had been born in 1952, and as he moved through his infancy and toddler years, his father had entered Singaporean politics. By the time the son was just two years old, Lee Kuan Yew had joined other British-educated and middle-class Chinese to launch the island’s People’s Action Party, lobbying for independence from a Britain that had been driven out by the Japanese but had then reasserted itself as a colonial master once the war had been won. Well-educated Chinese like Lee Kuan Yew linked with socialist-oriented trade unionists. The intellectuals understood British law; the unionists knew the masses working in Singapore’s new factories. From the alliance would emerge the particular characteristic of Singaporean political life: British-educated Chinese elite provided guidance while the masses gained a social welfare state. By 1959, Lee Kuan Yew had become the first prime minister of a Singapore moving toward full independence.

And his first-born son was ready for primary school.

Nanyang was the choice. Nanyang neatly symbolized the link between Chinese intellectualism and the aspirations of the Chinese working class.

Like the father, the son would eventually study in the center not only of the British Empire, but also of the new American one, graduating from both Cambridge and Harvard,

and by August 2004, Nanyang Primary’s most famous alumnus would assume his father’s mantle and become Singapore’s third prime minister. In his inaugural address, Lee Hsien Loong would sound at times as if he was reciting the Nanyang Primary School pledge.

“We always want to move on, do better,” he told his audience. Singapore needed to be “a community where every citizen counts, where everyone can develop his human potential to the full, and where everyone participates in building and repairing and upgrading this shared home.” Alluding to changes that were under way as a result of the government’s pursuit of new communication technologies, he said that young Singaporeans — that next generation after his own — had been groomed to be “a strong generation ready for the future.”

But the Nanyang graduate also acknowledged that a problem shadowed the island. Paradoxically, many of the young and most creative of Singapore’s citizens were leaving.  They were different, he said, this “post-independence” generation, especially the males.

“I was in Korea recently,” Lee Hsien Loong explained. “They gave me a definition of youth. They said, ‘A young man is somebody who can do an SMS” – a text message on a cell phone – ‘with one hand on the phone in his pocket.’”

It was a different kind of masculinity, a different blending of male body and desire and performance of gender not exactly described in the Nanyang School code.

“In Korea,” Lee Hsien Loong said, “young men like that changed the government.”

A decade after Lee Hsien Loong attended Nanyang Primary, another Singaporean family, the Koes, faced the same decision as the Lees had: where to send their first-born son to school.

The senior Koe ran a successful pharmacy company; the son, part of that first generation of Singaporeans born after independence, was skinny, bookish, and perhaps a bit on the hypochondriac side – although that seemed somewhat justified given that his male relatives had tended to die of hypertension at an early age.

His Chinese name was Koe Chi Yeow, born September 6, 1972. Unlike Lee Hsien Loong or Lee Kuan Yew, however, he would hardly ever use his Chinese name. Instead, he preferred his English first name: Stuart.  Even better, as he would come to sign it on his Internet blogs, he preferred “S2” which sounded like “Stu.” Perhaps not just coincidentally, it was also a pharmaceutical reference to the asthma inhalants used to open constricted airways.

Like the Lees before them, the Koes picked what they thought would be the best school. Once again, it was Nanyang Primary.

Young S2 seemed less than thrilled – at least when he later looked back and blogged about his years there. “I learnt later in life,” he wrote, “that [Nanyang] was where lots of snotty Chinese parents who ran large Singapore corporations or came from large snotty rich families sent their kids.”

At Nanyang, Stuart quickly found himself mostly attracted to playing with the girls at recess, but not because of any early blooming sexual desires. Just the opposite. For Stuart, the Nanyang dress code requiring short-cropped hair made at least some of the girls seem “butch”  – “butch in a big way, even before they were 12,” he would write. His mind had quickly noted the kinds of gender differences that being a girl or a boy made. The girls used words more acutely and, sometimes, more cuttingly. He liked that. He was interested in words and language – so much so that he would eventually list the radical linguist Noam Chomsky and the anarchist poet Arthur Rimbaud among the authors who changed his life. Ditto with John Rechy and his City of Night novel about a young male hustler’s journey through a marginalized world of prostitution and sex.

S2 wrote that compared to the girls at Nanyang, the Singaporean boys were “timid, wimpish, and general bores.” He longed for creative playmates, later writing that his likes included “good company, good food, good books, good films, beauty and creativity.” He described his “mission on earth” in a single verb: “create.” The type of person he liked was “someone I can go exploring the world with, someone intensely self-aware and earthy, equally grounded in the arts and sciences.”

His dislikes: “People who only add to the negative energy of the world” and those who favor the “status quo.”

Shortly after Stuart enrolled at Nanyang, Singapore’s government, then still headed by Lee Kuan Yew, made a fundamental decision that would shape much of the rest of S2’s life. Manufacturing jobs, the government believed, would no longer be enough to insure the future of the island’s social welfare state. Too much competition was coming from elsewhere in Southeast Asia and in that gradually opening behemoth, mainland China. The island’s commerce needed to metamorphose again. Singapore would instead engage the emerging global market for computer and information technology: chips and disks and all the accoutrements of knowledge and communication that went with them.

If Bali had developed the reputation in Southeast Asia of being the aesthetic paradise imagined by Walter Spies, and if Bangkok was the erotic paradise thanks to decades of fretful European worrying about promiscuous Thai men, Singapore would become the smart paradise.

The monumental change was planned to unfold in a very orderly fashion. From 1981 to 1985 — with Stuart and others of his age still in primary school — the National Computer Board would be established and a Civil Service Computerization Program begun. Government ministries would be computerized first, seeding a cadre of Singaporeans who would become computer-savvy professionals. The second phase would begin when students S2’s age reached high school in the late 1980s. Then, what was called the National Information Technology Plan would kick in, funneling government money to private businesses working in communication technology. The finale was to begin in the 1990s. Under the so-called “IT2000” master plan, computer-based information technology would be placed into every niche of the nation’s culture – at home, at work, at play. In this new high-tech Singapore, the city’s architecture and cyberspace were to be seamlessly stitched into a magical web of “smart” homes, “smart” office buildings, “smart” transportation hubs, and “smart” community centers.

It would all be a bit like the “modern kitchen, all white and shiny,” that Walter Spies had suggested his jail mate wanted.

A smart, orderly paradise.

A part of the IT2000 report described what would happen by presenting a hopeful novella. Each morning, the story ran, the fictional Tay family living in this smart paradise would awake to run its life through voice-controlled high-definition TVs hanging on the walls. The TVs would serve as picture telephones as well as interactive tutors for the fictional Tay children. The Tays would use smartcards with personal and medical histories. Because money could get dirty, the smartcards would also replace bills and coins. At Mr. Tay’s tailor shop customers would study different shirts on a screen without touching or trying them on. Mr. Tay could use an electronic scanning pen to change the designs to fit each body. Conveniently, that also left him a database about the physical construction of each of his customer’s bodies and how they did or did not fit certain norms. Some might be slender and toned; others muscular; some fat; some with big shoe sizes, some with small. Meanwhile, Mrs. Tay ran her insurance business from home on one of her wall screens. Whenever she needed a break, she played mah jong digitally with her friends, who were also taking breaks in their own homes and becoming pioneers in a new imagined world of virtual gaming.

Most important for school-age children like S2, the fictional son in the report — named Tay Leng Meng – would find his way home from school by tapping into public information terminals to locate bus routes. Tay Leng Meng would then sit in front of the wall screens to use multimedia databases working on school assignments about what the “old” Singapore was like — with its brothels and rubber warehouses.

A year after the IT2000 master plan was released in 1992, a writer for Wired magazine asked a provocative question: What would happen if Mrs. Tay decided to trade her insurance business for a more lucrative out-call sex trade?  Clients, like those at Mr. Tay’s tailor shop, could then use her husband’s databases and the wall screens to pick the bodies of the women — or the men — they most desired, shopping for those who were muscular or those who were lean, those with impressive shoe sizes, those with less. And what if the young Tay Leng Meng, instead of innocently finding his way home from school and dutifully working on his assignment, turned into what Wired called “a disaffected teenager who spends almost all his free time cracking private and governmental databases.”

That, the magazine suggested, was the kind of surprising scenario the government of the new smart paradise might not anticipate: the matchboxes Walter Spies had described gone to moving in surprising and disorderly chords.

Singapore’s official plan for students was simple: Stuart and his Nanyang schoolmates were to become pioneers in that brave new cyberspace where a transformative Scriabin-like symphony of sound, light and rhythm lived online.

But the last thing the soon-to-be S2 wanted to become was a fictional Tay Leng Meng writing a term paper about the old Singapore.

S2 wanted a new Singapore. And that database of men held the key.