John-Oliver pulled out all the stops for the gorgeous Singapore proposal he planned for his now-fiancée Cara. We honestly lost count of all the epic surprises he planned as part of this elaborate proposal. Our favourite surprise? He planned an “engagement-moon.” C’mon, that has to catch on, right? It just has to. Read on for all the squeal-worthy details.


“We met at work – we are both doctors and at that time, we were working on the same intensive care unit. Slightly unusually, our first date was an 8-mile run! Come to think of it, our second date was a run, too! Getting to know each other was so easy – we just clicked and we were so relaxed in each other’s company.” – John-Oliver


“We visited my parents for my birthday that year and I knew then that I had met the woman I wanted to marry (clearly she’d have to say ‘yes’’ though!). Cara moved in not long after that and the rest is history.” – John-Oliver


“I proposed to Cara at Raffles Hotel, just over two years after our first date. I had started thinking about the specifics of the proposal about nine months prior – my sister, brother-in-law and niece live in Singapore and as we were planning on visiting them for the Singapore Grand Prix, I thought it would be the perfect opportunity.

“I had surreptitiously found out Cara’s favourite engagement ring setting (round brilliant cut) the summer before in Tiffany’s in New York, so after my brother-in-law had recommended the jeweller he had used (Boodles), deciding on the ring wasn’t actually that difficult. I kept the engagement ring in a pouch in my wallet on the flight out, with the ring box in a sock in a shoe in my bag. There had been occasions when Cara had had my wallet in her handbag and unbeknownst to her, the engagement ring had also been in there in its pouch!

“The rest of the engagement planning was a little trickier, however, because I wanted a number of things: an amazing proposal setting, photographers to capture the moment, a special restaurant for dinner on the night of the engagement, and to go for a brief trip from Singapore to celebrate the engagement (an ‘engagement-moon’)! Quite a lot of planning and all from nearly 7,000 miles away!” – John-Oliver


“Despite all of our planning, there was still a last minute panic because it was raining early in the morning on the proposal day! Cue a flurry of texts back and forth between our Flytographers Michelle and Alvin and me with potential location changes within Raffles (Michelle and Alvin had been there the day before to scout the location, sending me videos of which entrance to arrive at and how to walk through to the proposal spot – instructions that I completely forgot in the heat of the moment!). In order to get Cara to Raffles without raising suspicion, my sister booked us a last-minute table for breakfast. When we got there, I made an excuse and went to find Michelle and Alvin. I came back to the breakfast table 15 minutes later with Cara wondering where on earth I’d been! I had to say that as a surprise, I had organized for us to have some photographs taken (Cara had mentioned previously that she would like more photographs of us together). So, taking Cara by the hand, we walked to meet Michelle and Alvin. After introductions and a couple of photographs, I got down on one knee and proposed.

“After the proposal, I felt complete and absolute love. I felt overjoyed and ecstatic and so wonderfully vulnerable – it was, and still is, the happiest moment of my life. I also felt relief – not that she had said yes (although it was incredibly nerve-wracking, I was confident that she would), but rather that I had had to keep so many secrets from Cara for so long, which I had hated doing, so it felt amazing to be able to tell her everything. I am so proud that Cara is my fiancée, and will be even prouder when she is my wife.

“Looking at the photographs brings back so many incredible feelings and memories. We have some of them framed and hung up in our bedroom. Michelle and Alvin captured the moment perfectly – I will never be able to thank them enough.” John-Oliver


“We then had the most amazing photoshoot at Raffles before celebrating with a Singapore Sling at The Long Bar. After that, we telephoned family and friends with the amazing news and a glass of champagne at the top of Marina Bay Sands overlooking Singapore.

“After reviewing a great number of restaurants for our celebration engagement dinner, I took the advice of my brother-in-law. The Tippling Club was the perfect venue, where we dined with my sister and brother-in-law. It was a magical evening topped off by partying the night away at The Podium Lounge.

“For our ‘engagement-moon,’ we went to The Datai in Langkawi, Malaysia. Booking that was tricky because Cara does not like surprises, rather she loves the anticipation! So she knew we were going there, but not the reason why. The last surprise I planned for Cara was to upgrade our flights back from Singapore without her knowing.” – John-Oliver

 Flytographers:  Michelle & Alvin in Singapore

Flytographers: Michelle & Alvin in Singapore

See more: couplesengagement – loveproposalSingapore