Date Night: Simon and Jin’s Intimate Rooftop Engagement Session


Of all the wonderful places to shoot an engagement, at home has to be one of our favourites. Simon and Jin met overseas only to discover that they live right across from each other in Singapore. In a nostalgic nod to their rooftop proposal, the couple took in the city sights over a rooftop dinner and dance at Simon’s home, in a series of narrative captures by Desmond Tang Photo.








































How did you meet and what was the proposal like?
“Jin and I met in Vietnam. I was there on a holiday and she was home for Christmas. Our mutual friend suggested Jin show us around Saigon. Upon returning to Singapore, I realised that she was staying in the building opposite where I live. Desmond features this building in our photoshoot albeit in a subtle way; in some photos Jin looks out from the roof at the blurred shapes of the building where she lives.

The proposal was a surprise. We were staying at the Padma Hotel in Bandung. We’d flown in just for the weekend, for a friend's wedding. After the wedding, she returned to a room with champagne and tulips (her favourite – trust me it’s hard to get tulips in Bandung). A handwritten note told her to meet me at the rooftop pool of the hotel, which is perched on a cliff overlooking the Bandung rainforest. I was waiting by the pool for quite a while, wondering if she would come. Finally she appeared and I proposed. In the moonlight, surrounded by jungle and mountains, with the soft sounds of the pool behind us, she said yes… after some thinking. *laughs*” ~ Simon

What was the inspiration behind your shoot?
“I'm an architect and Jin is a graphic designer. We approach our wedding as we would any project. We enjoy the idea of making something authentic and real to us on a personal level. We wanted our shoot to be us, real, and classic, and the process with Desmond was as such.

We spent months beforehand meeting to discuss the storyline – what kind of people we are, what we enjoy doing, our pets, favourite places, times and movies, colours of films we enjoy, photographs and music we love, and our travels.

Ultimately, we decided the shoot must happen in a personal space in order to for us to be at our most natural. It was shot almost entirely in my home, except for the MacRitchie scenes. All the props are our own and sourced over several months. The bike is the actual one I ride to work and the books are our books. The roof setup was personally done by me and a few buddies of mine. The food was cooked by my sister’s boyfriend and the wine was from my office. It was the most authentic and natural of situations.

I guess the inspiration was to capture us in our element, in our most carefree state possible – just the two of us enjoying each other for each other. Desmond captured this perfectly.” ~ Simon

Do you have any interesting moments or stories to share from the day of shooting?
“It was indeed eventful with numerous ups and downs.

These photos are so important to us and we really trusted Desmond to set the mood, colour tones and atmosphere as inspiration for the rest of the wedding preparations. We will be compiling the photos into a coffee table book. Jin will be designing it and our wedding will be happening in the fall of 2016, in both Singapore and Vietnam. In Singapore it will be an intimate dinner at the Clifford Pier, and in Vietnam it will be a river side wedding at Thao Dien Village resort.” ~ Simon

A word from Desmond Tang Photography…
“Simon and Jin shared a similar vision as me on how they wanted to be photographed for their engagement. I had a great time working with them; from understanding who they are and how they met, brainstorming ideas, down to the preparations. The whole process was really delightful and I was thrilled for the shoot!

We decided to split the shoot into three days, mainly due to the natural light that I needed and the limited amount of time I had with it. I tried to include as many elements as I could gather from them and chose a few locations that they could relate to. One was the rooftop of Simon’s apartment at East Coast, overlooking Jin’s old apartment. I thought it was a fun fact that they met overseas and then realised they lived just one street across from each other!

Like any other shoot; not everything goes as planned. We actually got really lucky with the weather and managed to catch a few good windows between the rain. Although the grey sky wasn’t my favorite option, I embraced the clouds and wind I was given. On the last evening, our generator failed to operate the lights on the rooftop; it was a nightmare. Luckily, we had enough extension cords lying around to reach a power socket that we found. Lights? Check. Food? Check. Beautiful-looking couple? Check. It’s time to wine, dine and dance.”



Thank you for sharing these beautiful images with us, Simon and Jin, and warmest congratulations on your engagement!



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Vendor Information
Venue: Groom’s home and MacRitchie Reservoir Park
Photography: Desmond Tang Photo
Hair and Makeup: Peacock Makeup Salon
Flowers: FarEastFlora