‘Will you marry me?’ I asked and he said yes: How 5 bold women in Singapore proposed to their partners

It’s a tale as old as time: Boy meets girl, they fall in love and after dating for a while, they apply for a flat together. After clearing 1,001 bureaucratic steps, the moment arrives when the boy asks: “Will you marry me?”

This story might ring true for many couples in Singapore, but not the ones CNA Women interviewed for this story. They decided to go against the grain and be the one to pop the question.   

"IT WAS SOMETHING I ALWAYS WANTED TO DO"

For Amanda Tay, proposing to her partner Solomon Ng was a long-held aspiration. When the couple, both 29, started applying for a Build-to-Order flat in 2019, the seeds of her plan began to germinate.

“It was something I always wanted to do for someone I had decided to spend the rest of my life with,” said Tay.

“At that time, we didn’t have a house ready, so I guess it was more special because it showed that I was ready without any ‘typical’ commitment.”

As fate would have it, the digital marketer had won a giveaway contest for a couple photo shoot, providing the ideal pretext for her grand scheme. With Ng being none the wiser, she arranged for her friends to join them at the “studio”, ready to execute a dance performance featuring his favourite songs.

“Solomon is an introvert and I know he wouldn’t have much of a reaction, so some of my closer friends were there to be a ‘cheer squad’ to avoid any awkward silence,” Tay said.

However, he inadvertently stumbled upon a rehearsal, and Tay had to change her choreography two weeks before the event in June 2022.

When the moment of truth arrived, Ng said he was “frozen in shock” when the love of his life presented him with a S$2 Pokemon ring – a token to symbolise their engagement until they could shop for the perfect ring together.

“It was a total surprise,” the finance analyst recalled, admitting that – just as Tay had anticipated -- his reaction fell short of the tearful displays often depicted in viral proposal videos.

"You know the perfect proposals on social media? The girl being proposed to (usually) cries buckets of tears. Compared to that, my reaction was more ‘stoned’,” he said.

His friends and family rallied behind the proposal, praising Tay’s confidence and playfully teasing him for not being one step ahead.

“The proposal serves as a great memory, but people (often) place too much emphasis on the event and forget there is still a good 50 years of commitment ahead,” he said, recognising the true significance of their engagement in the excitement of the moment.

The couple have set a date for a July wedding.

"I DID NOT EVEN THINK ABOUT WAITING FOR HIM TO ASK ME"

Natasha Saini, a commercial strategist, also had no hesitation in taking the lead. Chaitanya Sood, 32, was her “best friend” and them living together during the COVID-19 pandemic only solidified her desire to spend a lifetime with him.

“Honestly, I did not even think about waiting for him to ask me. I knew we both loved each other and I just went right ahead,” the 35-year-old said.

She kept her proposal plans tightly under wraps, confiding only in family members, a proposal planning company, and a photographer she managed to secure at the eleventh hour. The secrecy added to her nerves, which were palpable on the day of the proposal.

“You think men get nervous – I was all nerves on the day myself. What if he says anything other than a yes? So I made sure I held on to the house keys. If it isn’t a yes, he would need to find himself somewhere else to stay,” she joked.

The jitters heightened when it started pouring that evening in April 2021 – that she managed to talk him into a “picnic party” after the rain was a feat in and of itself. He couldn’t figure out why she insisted on dressing up, until a teepee hut and fairy lights – carefully relocated to a sheltered area – came into view.

“It was not until I actually proposed that he figured it out and we still have a picture of his rather shocked, happy face,” Saini beamed.

(She calls it the “most precious expression” she’s ever seen on her partner to this day; his friends called him a “blushing bride” after seeing the pictures.)

"When I finally realised that I was being proposed to, I was surprised, ecstatic, and overjoyed, in exactly that order,” Sood, a principal at a global consulting company, recalled.

As Saini did not know her partner’s ring size, she fashioned an adjustable one out of some string and threw in some Bugles (his favourite snack) to sweeten the deal.

“Both of us had known each other for three years then and had felt a very rare and special connection, so the answer had to be yes. Without a pause, without a doubt,” Sood said.

He was deeply touched by more than just the logistical feat of “Natasha’s heist”, as he fondly dubbed her proposal, which she managed while working 70-hour weeks across different time zones. Rather, it was her courage.

“It’s the vulnerability she showed by putting herself out there and proposing, knowing that there is a miniscule chance that the person on the other side may be unsure or, worse, say no,” he said.

The couple tied the knot seven months after her proposal, in November 2021.

"I NEARLY GAVE UP ON THE PROPOSAL"

If outdoor proposals are tricky in Singapore, imagine pulling one off in the blistering heatwave in Europe last year.

“Honestly, it was never something I seriously considered,” Joanne Low, a business development representative, confessed. She added that the idea to propose to her boyfriend, Nicholas Tan, was sparked by a friend who had been there and done that.

Conscious of her family’s traditional views, the 27-year-old kept her plan under wraps but took the unconventional step of seeking his mother’s blessing. Surprisingly, the latter proved to be more supportive than some of Low’s peers.

“The reactions were mixed. Some were genuinely excited and happy for me while others were like, ‘Huh! Why would you do that?’ To each his own, I guess,” she said.

The plan was simple: A couple photo shoot on a trip with their friends, a timely cue from the photographer and the proposal. However, the scorching 40-degree Celsius heatwave in Sicily, Italy, threw a wrench into her plans.

“It was quite disastrous… Nicholas suggested cancelling the photo shoot because of the unbearable heat and I had to convince him to go ahead with it,” Low recounted.

But their troubles were far from over. They struggled to hail a cab and couldn’t locate the photographer due to poor reception. Additionally, their friends, who were supposed to show up only after the deed was done, inadvertently revealed themselves.

“After waiting for about 20 minutes, I nearly gave up on the proposal,” she admitted.

It was Tan who persuaded her to persist. The photographer eventually located them, albeit behind schedule and with an unexpected backdrop far from the envisioned setting.

“The initial plan was for me to propose in front of the cathedral, but on the day, it was covered in scaffolding. Everything that could go wrong really went wrong,” she said.

Despite the series of unfortunate events, the proposal unfolded with Low on bended knee.

“At first, I thought it was a gag,” Tan, a sales development representative, recalled. “But when I saw the ring, I was overwhelmed with joy and very pleasantly surprised.”

He said yes, she delivered a heartfelt speech, and their friends reappeared with impeccable comedic timing, realising they had missed the entire occasion.

Asked about his thoughts on a woman-initiated proposal, Tan, 28, said: “I believe it is crucial for both partners to collaboratively determine what’s best for them rather than blindly adhering to conventional norms. I think it is beautiful that we are mutually progressing on our terms.”

The couple are planning for an end-2025 or 2026 wedding.

"I NEVER CONSCIOUSLY THOUGHT THAT PROPOSING WAS A MAN’S ROLE"

Recognising that she’s “not an easy person to surprise”, post-graduate student Christy Yip took charge during a campervan journey through Tasmania, Australia, in 2022. She was determined to propose to her boyfriend Jordan Tan before he could beat her to it.

“I never consciously thought that proposing was a man’s role,” the 27-year-old said. “I did search for other girlfriends proposing on YouTube just to get a confidence boost, though, because I hadn’t seen any before.”

The centrepiece of her proposal wasn’t a traditional ring but a Ring Pop candy and a deck of We’re Not Really Strangers playing cards, a game designed to bring participants closer through thought-provoking questions and prompts.

What Tan, a 27-year-old software developer, didn’t know was that Yip had edited one of cards with the all-important question.

To capture the moment, she had convinced him that she was filming a vlog of their trip – a ruse she kept up from the moment they landed at the airport.

“I was really nervous,” she recounted. “I literally had to play my cards right so that Jordan would receive the right card and I wouldn’t be proposing to myself.”

She carefully arranged the sequence and, fortuitously, the previous card said, “Tell me about the time you felt lucky that I was your significant other.” It was the perfect segue for a marriage proposal.

When Tan drew the card, he was at a complete loss for words, calling her “the ultimate romantic”. However, he confessed that the proposal wasn’t entirely unexpected.

“We had been ready to move on to the next stage of our relationship for the longest time. So, I was not particularly concerned about who proposed to whom,” he said.

“Don't get me wrong, I was still over the moon when she proposed!”

The couple’s parents weren’t taken aback either; it was clear to them that the two were made for each other and would eventually walk down the aisle. Their reaction, if anything, added a touch of comic relief.

“Jordan’s family literally said ‘chey’ when we told them we were engaged. They didn’t even ask for details,” Yip laughed.

The couple got married in July last year.

"YOU WILL MARRY ME"

You may have heard of a counter-proposal, a growing trend of women reciprocating after being proposed to. After her partner Joseph Tan surprised her with a ring in Calgary, Canada, in April last year, when she was on a solo trip, Grace Ann Chua decided it would be “meaningful to propose back”.   

The venue? Beach Road Prawn Noodle House – a beloved childhood haunt and a weekly tradition for him. It helped that the couple, both 30, is friends with the owner’s son, Bryan, who helped her bring the surprise proposal and after-party to life. The date? November last year.

Event planning is Chua’s bread and butter (she is the CEO and co-founder of a social organisation) and it showed in the elaborate affair she staged. Emcees and game masters were appointed, along with a “social media team” made up of friends with an eye for photos and videos.

On the big day, Chua lured her fiance to the vicinity with the promise of pizza, his favourite food, and suggested that they park outside the prawn noodles shop. There, a wild-eyed Bryan appears and asks for Tan’s help to “carry prawns into the shop”, where the entire crew laid in ambush.

“I was in awe,” Joseph, an operations director, recounted. “I stood there, calmed myself down, and said to myself: Let me appreciate and dwell in this moment. My follow-up response was, ‘Spoil market. What do I need to do next to one-up you?’”

After Chua delivered her speech, their friends made their entrance, holding signs that read “You Will Marry Me.”

“This was based on a meme he tagged me in when we first started dating. Also, because he had already proposed, he will marry me!,” she added.

She went down on bended knee in a skort she had bought specially for the occasion and a S$30 ring she found on Etsy. It was designed to resemble snow-capped mountains, a nod to the location of Tan’s proposal in Canada.

“I am extremely fortunate and blessed to be on the receiving end of the proposal… I feel like I am at the top of the world,” Tan said.

Chua said that the key to a meaningful proposal lies in considering the unique details of the relationship, whether they are inside jokes or shared milestones.

“It doesn’t have to be fancy or grand, unless that is your personality. It can be private and simple as long as it’s ‘you’. That’s what makes it special,” she said.

The couple will be getting married in March.