There’s a lot to juggle when it comes to nailing Valentine’s Day. So how do we know we’re doing it right? While there are plenty of gifts that are sure to light up any partner or pal, we thought we’d help nudge you in the right direction by asking people what their most memorable V-Day to date has been. From heartfelt gestures to unexpectedly simple dates, Stephenie Gee discovers our #legend100s’ favourite – and most unforgettable – Valentine’s Day memories

Bruce Tong @bruce_tong

“I’ve been single for a long time – haha – but my most memorable one was making a heart-shaped cake for my ex maybe three, four years ago. I rarely cook and it was my first time baking!”

Byejack @byejackk

“The day when I put out one of the sweetest songs I wrote, ‘February, 14’, but in reality I was alone for the whole day with no one to date. It was quite memorable.”

Cecilia Yeung @cceciliayeung

“One of my most memorable Valentine’s Days was actually right before the pandemic closed the borders. My fiancé (BF at the time) and I took a short trip to Japan, and what was supposed to be a sweet getaway somehow turned into… a mask-hunting mission. Every convenience store, every pharmacy we walked past, we’d pop in ‘just to check’. On the very first day, we found masks in a convenience store. I wanted to buy all of them, but he told me, ‘Leave some for other people lah’. So we only bought a few, thinking we’d find more later. But we didn’t. For the next three days, every shop was empty. That first pack we left behind? That was the last one we ever saw. And honestly, that’s why it became memorable – travelling lightly, laughing at ourselves and realising that sometimes the most romantic moments are the unexpected, silly ones you share together!”

Jenny Tsang @tsangtastic

“When we tried making a fancy dessert we saw online and it turned into… whatever that bubbling purple situation was. We kept pretending we were chemists and named it ‘The Valentine’s Volcanic Incident’. We still ate it, too. Zero shame.”

Jonathan Jay Lee @jonathanjaylee

“My most memorable Valentine’s was about 16–17 years ago. The girl I liked at the time was still with her boyfriend so I was in limbo. But in solidarity with a friend of mine – in a similar situation – we decided to go out and make a day of it together. She made chocolates that we gave out to random people we met along the way. I wouldn’t have had the audacity to do something like that on my own, but maybe because she grew up in Brazil it was easier to roll with her and be brazen. I specifically remember the local siu yeh spot in Mong Kok on Dundas Street gave her fishballs and siu mai in exchange for some of her chocolates. That Valentine’s was memorable not because it was celebrating with a significant other, but that we could celebrate Valentine’s in spite of it.”

JuJu Chan Szeto @jujuchanszeto

“This year was our first Valentine’s Day with our baby, and it instantly became the most memorable. Life feels so full now – the tiny smiles, the new routines and the way our home feels warmer with an extra little heartbeat in it. Our celebrations weren’t about candlelit dinners anymore, but about enjoying the everyday moments together as a little family. Somehow, those moments felt even more romantic and meaningful. It was a beautiful reminder of how much our love has grown and how special this new chapter is.”

Ka Yan Tam @nomkakaii

“In high school, we used to have an anonymous rose-sending service, and I sent a rose to my crush then – we were close friends and sat together in class often, and whenever I had math questions, I would ask him for help. The rose would come with a note and all I wrote was ‘happy valentine’s day :)’. We had a box in the corner of our homeroom, and I sneakily put in the money and the text. Thankfully, the note was written by the service (other students), so no one could guess through handwriting. When people found out that he received a rose, they started speculating around but somehow the suspicion never led to me. It was fun for me to see the ‘hunt’ happen in real time. I only told him that I sent him a rose three years afterwards.”

Sabrina Cheung @sabrinasa

“My most memorable Valentine’s Day probably dates back to when I was in primary school. I received chocolates from a boy I liked (shy) and also some other boys, which made me very happy. It was a very cute and memorable feeling – quite incomparable to those I’ve felt after growing up.”

Sophy Wong @sophysophyw

“My most memorable V-day was also my birthday celebration as they’re two days apart. My partner cooked me Mexican food and made our living room into a restaurant which was so fun! Even the tortilla was homemade. Impressive. :)”

Thaimay @thaimay_spicy

“Last year as Valentine’s Day was approaching, a friend’s boyfriend invited a bunch of us (including me) to help him propose. The girl and I are about the same age, and so while we were rehearsing the proposal together as a group, we couldn’t help sighing – and laughing – about why our own journeys in love and relationships hadn’t gone as smoothly as others. The girl said yes, and we were all deeply moved and genuinely happy for them. But it inevitably made me wonder if I was lagging behind everyone else in life. This year on Valentine’s Day, I saw a female friend on social media – who got married and had kids very early – posting some heartbroken quotes about being let down. I suspect she got divorced, but I didn’t ask too much. After all, whether it’s getting married or getting divorced, it’s all about becoming happier yourself. There’s no such thing as falling behind.”

Veronica Li @vnikali

“My most memorable Valentine’s Day would be my and my husband’s first 19 years ago. We were at Discovery Bay and suddenly along the beach there were candles set in a heart shape. It wasn’t planned but everything happened so organically, like a Korean movie scene. It was like the universe was sending us a message wanting us to know that we are meant to be. It was also freezing cold that night, so Lucas took the opportunity to put his arms around me as we watched the fireworks starting over in Disneyland. It was all very magical and romantic. The funniest thing was that Lucas was surprised himself that day as well!”



See also: His and hers watches for Valentine’s Day 2026