With her blond bob, convertible car, cigarette in hand and cropped top emblazoned with the letters YOLO ("You Only Live Once"), this is an Alice in Wonderland the world has not seen before. Like Lewis Carroll's original, this cartoon Alice is curious about the world – "she gives up her cash to fly around rash" – but the moral here is that this twentysomething Singaporean is so busy being "wild and reckless" that she stands to lose her chance of starting a family.

Welcome to adult education in marriage and fertility, Singapore-style.

"Alice" is one of 15 fairytales revamped for a new government-backed scheme to encourage Singaporeans to get married and start having babies earlier. Faced with a rapidly ageing society, skyrocketing housing prices, low birth rates and a population that works the longest hours in the world, this country of 5.3 million people has made various attempts over the years to encourage its citizens to marry and procreate, from government-funded speed-dating schemes to educational flyers on how to flirt. Now, however, it is changing its tactics in search of a happy ending.

An illustration from the Golden Goose fairytale about declining fertility. Photograph: The Singaporean Fairytale

Aimed at 21- to 30-year-olds, the "Singaporean Fairytale" was created by four final-year university students who wanted to "find an interesting way to connect with young adults … on what it takes to start, live and be a family in Singapore", says the project manager, Chan Luo Er, 23.

"Fairytales are very accessible, as almost everyone grew up with a fairytale or two – our little poem on a woman's declining fertility as she ages ties in quite nicely with the Golden Goose."

The fairytales – which have been distributed by leaflet to universities around Singapore – include versions of Cinderella, the Three Little Pigs, Rapunzel and Snow White, each involving a reworked tale that relates to fertility, sex or marriage, and a resulting moral. The lesson with "careless" Alice, for example, is that "the extended adolescence of twentysomethings today has a biological cost for women" and the story ends with a stark warning: "After 40, [fertility] drops 95%."

The scheme has proved popular on both its website and Facebook page among students who appreciate its attempts at creative humour. But it comes at a time of widespread disillusionment with the government's efforts to boost population figures. Just last month, parliament passed a controversial white paper that will see the island increase its population by a third by 2030, in effect granting citizenship to more foreigners and squashing the native population to just over half the total, in order "to remain a key node in the network of global cities". .

Perhaps more tellingly, the fairytale initiative raises the question of what exactly the Singaporean fairytale is – a notion that the government and the public have been debating in recent months.

"When we were much younger, I think many of us were exposed to the idea of obtaining the five Cs: cash, car, condo, country club and credit card," says Chan. "But we think times are changing … For us, the Singaporean fairytale is about living life the way that makes you happy – so it could either be setting up your own business or even starting a family early."

Activists and critics say too much stress is placed on Singapore's TFR – total fertility rate – when the city state really needs to assess its work-life balance. They say such government schemes fail to account for women who choose to be single, do not want babies, or are in non-heterosexual relationships.

"These fairytales barely begin to scratch the surface of the overwhelming decisions Singaporeans face when considering [life's] trade-offs and do little to provide them with the information they need to help them with that," wrote Singaporean blogger Fikri Alkhatib in response to the group's notion that "[Singaporeans] can have it all, if only you choose to".

"Singaporeans aren't just 'choosing' not to have it 'all'. That's pretty extraordinarily insulting. They either cannot, or they choose to reject the idea of your 'all'."

Critics point to other recent schemes promoting conventional themes about women's roles in society as proof that Singapore is simply out of touch. In the Singapore Dating Guidebook, the modern-day, corporate woman is called a "Singapore New Independent Princess" (SNIP) and is offered dating advice such as: "If he lets you pick up the tab or worse – expects payment-in-kind – RUN!"

"It entrenches all the stereotypes and it's unfortunate that it's supported by the government," says Corinna Lim of Singapore's Association of Women for Action and Research (Aware) of the similarly outdated fairytale advice.

"It's an old-fashioned way of trying to solve this problem. It's going backwards when going forwards would be what Scandinavian countries are doing – making it easier for women to have babies and allowing men to take part [through paternity schemes], instead of pressuring women by saying they're not married yet."

The government recently passed a £1bn parenthood and fertility package which will fund assisted reproduction and finally give fathers a week of paternity leave. It has also released a series of educational cartoons for those looking for love, with tips such as: "Look out for a favourite topic your date has, or anything that your date has mentioned – this gives the feeling that you are interested in your date," and: "Scout your surroundings for possible chat topics, or comment on an interesting accessory your date is wearing" to avoid awkward conversation.

But the mere fact that the government feels it has to teach its citizens how to flirt may alone show why the population isn't higher.

Lim says: "It's an indication that our education system, in focusing so intensively on grades, has failed to give us the life skills we need."