He says: "I spent more time in Paragon than anywhere else. I was there sometimes till 3am. I met friends for lunch and dinner, usually in the area, and then I went back to the shop to take care of business."
After Bacchus at Paragon closed, he missed the homey, "organised mess" of a place; a spot in town where he could meet his wine customers and friends, as well as share with other oenophiles.
The seasoned wine seller acknowledges that opening a store amid the softening retail scene may seem foolhardy to some, but he believes brick-and-mortar shops are still relevant.
"If I'm serious about it, there is enough to be made. But I'm quite laid-back, I don't push myself too hard," he says in his characteristically unhurried cadence, with a gentle chuckle at the end. "It'll be a very busy time ahead, but as long as I enjoy it, then never mind."
His approach to running his wine company, which at one point had five outlets in Singapore and one in Kuala Lumpur, stems from his unorthodox business principle that is founded on friendship.
For one thing, he allows his customers-turned-friends to buy bottles of wine on interest-free credit and pay later, a business practice more common in heartland provision shops. And he admits to being "a bit slow" about collecting payment.
"Sometimes, my customers will chase me to collect money from them," he says with a mixture of amusement and embarrassment.
A long-time customer of his, Dr Wong Chiang Yin, 48, a public health specialist working in the private sector, says Mr Tay used to tell him to "pay later, take first", when he was a young doctor starting out in the workforce.
Dr Wong says: "He kept the IOUs in a book, but lost it when he was moving from one unit in Paragon to another. Most of us wanted to pay him back, but he said to forget it. Now, we insist on paying him first."
He adds: "We buy wines from him not because his price is the best, but because he has been a part of our drinking education over the years and he has become a friend.
"And as a friend, he doesn't make demands of you. He is not judgemental about people, only wines."
When asked if his customers take advantage of his goodwill and if it hurts the business, Mr Tay says without rancour: "If they don't pay, I'll take it as my treat. The cash flow can sometimes be a bit tight, but we manage."
He adds: "The business is not money-making, but my profit is the joy of knowing friends and the good food and wine that I've had all these years, which are better than profit in monetary terms."
He speaks with quiet pride about his "Monday lunch group", which has been meeting almost every week for more than 18 years.
Initially, it was a weekly lunch catch-up with an elderly customer who lives near Paragon, but other wine-loving friends were invited to the lunch over time and the group now comprises about 10 people.
They usually dine in Orchard Road, with each person bringing a bottle of wine and the bill for the food split equally.
His emotive approach to his wine business belies his deep knowledge and seriousness about wines.
For him, a good bottle of wine goes beyond hype and stereotype.
He says: "As long as someone has money, he can buy an expensive wine. But to be able to discover something good without having to pay a lot is more rewarding."
He practises this at his meals with his wine connoisseur friends, occasionally opting for choices that surprise. Once, he brought a Chinese grape wine that some mistook for a wine from Bordeaux and another time, an affordable Californian pinot noir that was mistaken for a pricey Burgundy.
Dr Wong says that beyond his friendship with Mr Tay, he continues to patronise Bacchus because "Don brings in interesting stuff, things you don't usually get at other shops, and he takes pains to introduce quality wines at a good price".
Established wine writer and wine consultant Ch'ng Poh Tiong, 60, calls Mr Tay "the ultimate ambassador of wine", having been in the business "before wine became fashionable in Singapore" and for showing no snobbery.
Mr Tay's informal education in wine, beginning in the 1970s, explains this.
Like many of his peers then, he finished his O levels, completed national service, then joined the workforce.
His family was not rich, but neither were they in need. His parents worked in the spice business and he had three older sisters.
The Victoria School graduate, however, was ambitious, and after a year in his first job as a sales clerk at a soft drinks bottling plant, he applied for a job as a beverage salesman, which paid better.
He was hired as a wine and spirits sales representative by Boustead Trading, even though the only kind of alcohol he could afford to drink then was beer.
"I learnt on the job," he says. "The winery principals would come to Singapore to organise dinners and talks for us. I also read wine magazines."
His limited knowledge of wines at the start, though, did not handicap him as a salesman selling to restaurants, clubs and bars.
He says: "If you visit customers regularly, tell them about your products and have a good personality, you will do your job well and your customers will be keen to invite you to wine tastings and dinners."
These opportunities exposed him to many wines and helped him hone his palate.
Later, he was recruited by another trading company, Caldbeck Macgregor, to sell its wines, before he joined Daimaru in Liang Court.
The change from distribution to retail proved pivotal to his career. It allowed him to meet and connect with people from all walks of life - including the rich and famous - over wine, which he deeply enjoyed.
It is not the hobnobbing that appeals to him - "I don't serve customers faster or better just because they are rich or powerful" - but the unlikely friendships that form, transcending status and class.
He stayed with Daimaru for five years before re-joining Caldbeck Macgregor as general sales manager and then finally returning to wine retail for good in 1991.
He opened the first Bacchus in Paragon with a a sleeping partner and a capital of $200,000 from his savings. He also expanded into Yaohan supermarkets under the shop name, Opus, and opened a Bacchus branch in Malaysia that is now run by his cousin.
From 2003 to 2009, he also ran Bacchus @ Waterboat House, a wine bar with a small food menu at The Fullerton Waterboat House.
The business expansions were funded by his savings and although they were not loss-making, neither did they make him rich; he lives in a Housing Board maisonette in Bishan with his wife, May Ngoh, 68, a retired civil servant. His three daughters are married. One works in financial technology, another in marketing and the third is a housewife.
He closed the Opus outlets when Yaohan shut down in the late 1990s and did not continue Bacchus @ Waterboat House when it became one too many outlets for him to juggle.
Through it all, he has witnessed the ascent of the wine-drinking scene here, from when it was a coup for Daimaru in Liang Court to have a walk-in temperature-controlled wine cellar, while under his supervision, to the fading novelty of seeing people drink wine at zichar stalls because it has become ubiquitous.
He attributes the rising popularity of wine in Singapore to increasing affluence, growing sophistication among diners and an awareness of wine's health benefits. He credits his many years of wine- drinking for keeping his heart healthy.
Customers, he notes, have also learnt to evaluate wines more confidently and become less obsessed about the number of points a wine earns from a wine critic.
He has also seen the rise of the trend of online wine sales. In fact, Bacchus has an online store which Mr Tay's youngest daughter, who has a background in IT, helped set up in 2014. It has not attracted much sales, though, because unlike other online wine stores, he does not price products lower than what he offers in his shop.
If there is one thing he regrets about his long, illustrious career in the wine business, it is that he sacrificed time with his family while his daughters were growing up.
He says: "I spent so much time at work that I neglected my family. I could have chosen not to, but I wouldn't have had so many friends.
"Still, I regret not spending much time with them. But once it's over, there is no going back."