Lawyer Yeo S.E., 39, has a group of close female friends around her age who are all single.
According to her, they had channelled all their energies into their careers, but very little into finding husbands.
"We spent the previous decade telling ourselves that we're happy as we are, and if it happens, it happens," she says.
Three years ago, hoping to get over an unrequited crush, she took matters into her own hands and joined the OkCupid dating website. At that point, she had been single for 12 years.
Three years later, she has gone on dates with men in their 30s, 40s and 50s, but has remained single. As have her friends.
Ms Yeo is part of Singapore's swelling ranks of "singles" - a term used by statistics gatherers to define someone who has never married - who are aged 35 and older.
In 2004, there were 844,100 Singapore residents who were singles, compared to 1,048,100 last year - a jump of almost 25 per cent over 10 years, figures from the Department of Statistics show.
The number of singles also rose across all ages surveyed, but the sharpest spike was in the 50s age group. The number rose from 43,100 to 75,600 between 2004 and 2014 - or a jump of 75 per cent.
In a sense, these numbers are not surprising as marriages worldwide are following the same trend: people are getting married later - or not at all.
Delaying marriage is reflective of most developed countries, says associate professor Paulin Straughan, a sociologist at National University of Singapore (NUS).
The main reason for delaying marriage is "competing life goals", she says, such as a prolonged period in formal education and career.
She adds: "When you're older, you're also more likely to know what you want and less likely to compromise."
The median age for first-time grooms in Singapore rose from 29.1 years in 2003 to 30.2 years in 2013. For brides, it rose from 26.6 years to 28.1 years.
But there is another set of figures. In the Marriage and Parenthood Study 2012, a survey commissioned by the National Population and Talent Division, 83 per cent of single respondents indicated that they wanted to get married.
If so many people want to put a ring on it, why is it not happening?
Older singles Life interviewed say the challenges they faced include ambivalent attitudes towards dating, dwindling social circles, a mismatch in expectations and a self-sufficient lifestyle.
This might seem counter- intuitive at first glance.
By all accounts, dating culture should be burgeoning in Singapore with the growth of online dating and dating apps such as Tinder.
Moreover, dating agencies in Singapore have also seen a rise in demand from older singles - as well as interest from divorcees and widows.
CompleteMe, a dating agency with a 3,000-strong database, set up a personalised matchmaking service for above-35s last year that has since seen a 40 per cent rise in customers.
Ms Anisa Hassan, managing director of It's Just Lunch Asia, which matchmakes professionals over a meal, says: "In the past, people who were married before might have felt that the best years are behind them. Now, more divorced persons have come forward."
In 2004, when the company started, 20 per cent of its clients were divorced or widowed. Now, 40 per cent are divorced and 10 per cent are widowed.
But attitudes are hard to change: There is still a lingering sense of embarrassment and conservativism about putting oneself out there, especially for older people in the dating pool here.
The problem seems to be worse online. Ms Yeo, for example, sees a marked contrast between men in Singapore and those from abroad.
When American men sent her online messages via OkCupid, an international dating website, she could find and identify them on Facebook and LinkedIn. Dating in Singapore was far less transparent.
"There were men who didn't want to give their real names or say what they did for a living. Some said on their profiles that they were married but were looking for 'friends'," she says.
There are also those who find online dating exhausting, meeting person after person on first date after first date.
Take bachelor Benjamin Koh, 36, a consultant in learning and development at a corporate training firm, who three years ago gave up on the Lovestruck app he used to meet people.
He found the constant search for romantic possibilities tiring and fruitless.
"Sometimes I would meet someone who I may not have had any connection with. I'd think, maybe another girl would be better," he says, which would spur him to get on the dating treadmill again.
Having given up on dating apps, he says he still wants to find a wife who shares his Christian faith. Now he is looking among his church circles.
Another common reason that older singletons give about their lack of prospects is their shrinking social circles.
As they get older, more of their friends get hitched and start families. The friends have less time to hang out and have fewer new friends to recommend as possible matches.
Finance analyst G.V. Kang, 40, who has never had a relationship, puts it this way: "As a single, you tend to hang out with singles. We tend to get 'more single'."
There have always been more women than men in her life. She was from a girls' school and mostly socialised with the same group of friends through secondary school, junior college and university.
In her business administration course at the National University of Singapore and at her places of work, women also outnumbered men.
Two years ago, she attended events organised by dating agencies, but found it "draining and depressing" when she did not find a suitable match.
One criterion for her partner is that his salary should be similar to hers, that is, at least $9,000 a month, an amount she says is "realistic" for someone in his mid- to late-40s.
He should also be pleasant looking and have good values.
Expectations of what a partner should be like are thorny issues to navigate.
Life found that men's concerns tend to revolve around appearances and child-bearing abilities of their partners, while women's preoccupations centre on financial stability in their potential husbands.
Private investor James Foo, 44, who has gone on dates via a dating agency, admits that he is "quite picky in terms of looks".
But he counters that women in Singapore also have very high expectations.
Those he dated tried to suss out, for instance, whether he owned a car by asking if he knew where to park at certain locations.
On the other side of the fence, Ms Eunice H, 43, who lost her husband in a traffic accident three years ago, recently felt ready to look for a new partner on dating websites and agencies.
She found that many guys were tactless pragmatists.
In a first phone conversation, a man rejected her because he said he needed a woman young enough to bear him children.
And sometimes, singletons are too independent and comfortable with their lifestyle to make the effort to find a partner.
Ms Wee Le Fong, 40, a former air stewardess of 11 years, wonders if she has led the lifestyle of a cabin crew member for too long, and is too used to doing things on her own. She is now an administrative associate at a bank.
She does not go clubbing and seldom takes the initiative to meet people, prefering to leave such things to chance.
"Mainly, I work and spend time with my parents, who are very old, and the rest of my family. I sometimes spend weekends with my elder brother and sister and their children," she says.
"A friend once said, 'You're content with the love you already have from your family.' I think it's a bit accurate."
For older people who have had past relationships, there might be another factor that complicates dating: children.
Mr Victor Chua, 50, who runs his own tour operations business, lost his wife seven years ago when she was knocked down by a lorry, leaving behind their son, who was just one then.
Four years later, he started a relationship that lasted a year.
It broke down because the woman "didn't realise that caring for a child was so tough".
These days, Mr Chua, who mostly finds dates through work, says anyone he has a relationship with has to understand that "my time will not be spent entirely with her. I find I'm more attracted to divorced women who can handle my kid because they have kids too".
Father and son are so close that his son comes along on dates.
"It's more honest, more real. We might go on those dates for a simple dinner at a cafe, no pubs or discotheques," he says.
"My son asks me, 'when are you going to give me a mummy?' I say, 'we choose a mummy together.'"
At the age of 48, fresh out of a 20-year marriage, and with a son who has autism, Mr Wong Ying Yuan decided to try online dating.
Putting his profile picture on an online dating site, he said, was like trying to sell "a second-hand golf set".
At social events organised by a dating agency, he found himself sitting across women in their 20s. Problem was, he felt like he was talking to his niece, who is 24.
The adjunct lecturer at Singapore Polytechnic, now 50, has not given up on the search for a life partner.
But he takes a more low-key, relaxed approach now, guided by the philosophy of que sera, sera (whatever will be, will be).
After all, he says that "the status quo is okay".
To help things along, he signed up with CompleteMe, whose services include speed-dating events held in restaurants.
But now he has wised up and attends events targeted at over-35s, every two months or so.
Via the Lovestruck dating website, he found a girlfriend.
But the year-long relationship floundered last year when he brought up the topic of getting engaged.
He says that the woman, who was in her early 30s, did not want to take things further, choosing to focus on setting up a beverage business instead.
He tells his dates about his only child Leo, 14, "as early as is convenient", as a future partner "might feel a bit cheated" if he introduced his son to her only when the relationship was getting serious.
He adds: "I expect the person to be faithful and someone I can trust with money. I must also be able to answer the question, can I trust her when a special needs child is involved?"
He feels that his marriage broke down in part due to the stress of caring for Leo.
Now, he shares custody of the boy with his ex-wife.
In fact, because he trusted his ex-wife to do the best she can for Leo, there had been a period when he was reluctant to accept that his marriage was over.
"I asked my ex-wife more than once, 'Can we get back together?' I found that our son wanted us to reconcile too.
"She said, 'Go find a girlfriend.'"
So he tried, and is still trying. Perhaps because he had met his ex-wife at a tea organised by the now-defunct SDU (Social Development Unit), which was the matchmaking arm of the Government, Mr Wong found that he was "open to matchmaking".
Outside of dating, he occupies himself with causes and pastimes to enrich his life.
On weekends, besides spending time with his son, Mr Wong sometimes volunteers with a group that practises mindfulness.
He enjoys travelling. This year, he set up a small shop and cafe in Kathmandu, Nepal, a country that he has visited several times.
He is confident that he would make a good partner.
He says: "While I can be alone for the rest of my life, I'm looking for a stable, exclusive relationship.
"If not for the divorce, I wouldn't be on the market.
"I'm branded goods, though slightly worn."
After the end of her second marriage about five years ago, Ms Shamim Moledina, 68, did not expect that men would approach an older woman like her.
She was chatted up by men she met in different situations, including through her club, Singapore Recreation Club, at dinner parties and at community centre events. Some men sent private messages on Facebook.
"They were mostly in their 60s and many of them were married," says Ms Moledina.
Once, during what she thought was an innocent tea with a married acquaintance, she realised that he wanted something more when he urged her to call him whenever she felt lonely.
Despite these experiences, she has not ruled out dating, but would only go out with people she knows and trusts.
"I'm not the kind to have dinner at somebody's expense if I'm not interested," she says.
"I also know I get attached very easily. If I go through a break-up, it's hard for me."
Regarding dating prospects of women her age, she says that while some are lucky in finding a good partner, it can be "scary".
"Well-to-do women might get taken advantage of. Also, some people I know have been conned by men they met online."
After the end of her second marriage, which had lasted 22 years, there was a period when she felt "lonely and helpless".
"I was quite dependent on my ex-husband. I felt the need for a companion at that time."
She is financially independent although she had been a housewife since she was in her 20s. Her two adult children from her first marriage of 19 years live in France and Britain. She and her second ex-husband, a retired engineer in his 60s, had travelled and played competitive bridge together.
She attributes her current reluctance to date to a "very protected" upbringing.
Born in Bombay the fourth of six children, she lived in India, England and Pakistan as the family moved on account of her father's work running an import and export business. She "regrets" that she was never allowed to go out with boys for fun. Her first experience of love, as a shy schoolgirl of 18, was conducted mostly through letters.
She has had only two long relationships with people she had known previously. Her first marriage, which ended in divorce, was a matchmade one while her second husband is a relative.
Two years after she divorced her second husband, they got together briefly again. "I had been very hurt, but my heart is very soft. I had been with him for so many years," she says.
She and her ex went on dates like any other couple, having meals together and going to places such as the Botanic Gardens and museums.
She "found the strength to end it" when he asked, after two months, if he could date other women as well.
Now, she keeps herself busy with bridge at various clubs, as well as ad hoc volunteer projects, such as organising clothes donation drives for foreign workers. She travels a few times a year to visit her son, daughter and other relatives.
"I'm set in my ways. If I ever have a man, my whole life would change. I'm not prepared for that," she says.
A version of this article appeared in the print edition of The Sunday Times on July 19, 2015, with the headline More singles than ever looking for love. Subscribe