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"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.
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.
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.
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.
But he counters that women in Singapore also have very high expectations.
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.
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.
Sometimes I would meet someone who I may not have had any connection with.