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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). I sometimes spend weekends with my elder brother and sister and their children.
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. Ms Yeo, for example, sees a marked contrast between men in Singapore and those from abroad.
When American men sent her online messages via Ok Cupid, an international dating website, she could find and identify them on Facebook and Linked In. "There were men who didn't want to give their real names or say what they did for a living.
"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.
Now, 40 per cent are divorced and 10 per cent are widowed.
Having given up on dating apps, he says he still wants to find a wife who shares his Christian faith. 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. Kang, 40, who has never had a relationship, puts it this way: "As a single, you tend to hang out with singles.
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.
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Expectations of what a partner should be like are thorny issues to navigate.