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".
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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.
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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.
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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."
This article was first published on July 19, 2015.
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