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The Ultimate Men's Guide to Proposing Properly!!!

Updated: Apr 18, 2022

Think it's time to pop the question? Not sure what to do? Featured in Yahoo News as one of their favourite proposal videos, here's a few tips from Bobby Stryker to help you get the answer you want! Good luck!!!

On August 3rd 2013, I proposed to the most amazing woman I’ve ever met, the scarily smart and talented Juliana Chong of Now a year and a half later, I feel like I’m the happiest man alive. We tied the knot last year and I swear, there really is nothing better than waking up next to the person of your dreams every day.

I used to love hearing about how my dad met my mother, how they tied the knot, what life was like when I was born. Sadly they don’t have any photos or videos of their wedding so I will never really know what it was like. With this in mind, when I proposed to Juliana, I wanted to make sure the moment was caught on video. I really wanted to immortalize the moment so that we could both look back and reminisce about it, as we grow old together, as well as share the moment with our families and future children. It is a moment which we now both hold very close to our hearts.

The video was uploaded to YouTube so we could show our family and friends without the need to lug around DVDs and thumb drives. What I didn’t anticipate is that other people would enjoy watching the video too. I suddenly had guys asking me for advice and women asking me to talk to their boyfriends and advise them on how to propose. So here it is, for your viewing pleasure, my proposal video:

No one was more shocked than me when Yahoo News featured my proposal as one of their favourites:

I really don’t know if I did anything out of the normal and I definitely don’t claim to be an expert on the matter, after all, I’ve only proposed once in my lifetime. If you look at what I did, you can see that actually it’s a pretty understated affair compared to some of the things you can find online.

Here are some of the things I felt I had to do. They were right for me and who knows, maybe there’s something useful in here for you too.


1. She’s the One

Marry the woman of your dreams! Now this may sound like common sense, but common sense hasn’t actually been common since the age of the dinosaurs.

When I started thinking about proposing to Jules, I knew I wanted to spend the rest of my life with her. We had talked about growing old together but I had never explicitly mentioned anything about proposing or getting married. But despite this, deep down, I knew that if I asked her to marry me she would say yes, simply because we were so in love.

I think this is really important. If you are not sure about whether your other half would say yes or if you have doubts about whether your partner is ‘the one’ then she might not be. Only you can figure out this conundrum.

All I can say on the matter is don’t short change yourself! Don’t make the mistake of marrying someone out of desperation or fear of being alone, that’s a recipe for disaster and chances are you’ll end up in Splitsville.

You only have one shot at life so if your gal doesn’t make you feel that true inner happiness, the kind of happiness a kid feels opening his presents on Christmas day, then you’ve really gotta ask yourself if she’s the one.

2. Escape Plan

Now you’ll hear a lot of people say that a proposal should be something private, between you and your wife-to-be, or that planning something extravagant is just attention seeking behavior. Well, I don’t think that’s necessarily true.

Think about it like this. Most guys don’t do much for their gals on a day-to-day basis. There’s no point denying it, most guys are lazy! So do you really want the day you propose to be the same as any other lazy day? It risks giving the impression that it doesn’t mean much to you, that your intentions are perhaps not sincere, that maybe you don’t even love her. Basically it’s just not very nice.

This is probably going to be the only big surprise you will ever need to plan in your life so if you still can’t be bothered to put in some effort, then that speaks volumes about your character and your relationship.

What are you really saying if you ask her to marry you while you’re in your singlet and flip flops on the way to the supermarket? Where’s the passion? Where’s the romance??

It is exactly because men are so lazy, that if we do plan something and do something special, even if it’s small, it still means so much to our other halves! It shows you’re willing to go that extra mile for the woman of your dreams, even if it means going out of your comfort zone. She will appreciate it.

You may have a girlfriend who is really practical, who says she doesn’t like flowers and surprises, they might say the whole getting down on one knee routine is cheesy but I’ve never met anyone who wasn’t touched and happy afterwards. It’s just the right thing to do.

3. Father of the Bride

As scary as it was on the actual day of the proposal, nothing beats how I felt when I spoke to Juliana’s father to ask him for his permission and blessing to ask for Juliana’s hand in marriage.

I understand that this is not common practice here in Singapore but it was definitely the right thing to do and something I strongly encourage all guys to do before they pop the question. It’s respectful and will leave you in good standing with the parents.

Juliana’s father gave me not only his permission and blessing, but also his promise that he’d kill me if I ever hurt Jules! Haha!

He also helped me rally the rest of the family and ensure the surprise was kept a surprise.

4. The Lord of the Rings

Now I’m gonna tell you right from the get-go, there is so much advice out there about buying engagement rings and actually it’s mostly garbage.

You’ll read articles telling you to spend 2-3 months salary, you should look for this and that, but at the end of the day it’s all pretty meaningless.

I don’t believe you can be so logical when it comes to matters of the heart.

Remember, if she says yes or not depends on who your are and where you guys are in your relationship. Proposing with a giant rock will not increase the chances of her saying yes and actually may reduce your chances of success, especially if you’ve spent beyond your means, if it gives the impression you are financially reckless and spendthrift.

Remember point number one; you should already know that she will say yes! The proposal ring is a symbol of your commitment, not a means to buy her affections and get her to say yes.

Spend what you think is right, follow your heart. There is no magic equation. Perhaps go and see a few rings to get a feeling for how much they can cost. If a certain amount feels like it’s too little for the love of your life, spend more, if a certain amount seems too expensive then spend less.

Next is ring sizing. This is tricky because you obviously don’t want to ruin the surprise. I’ve always enjoyed wearing rings as a fashion accessory, so when Jules and I first got together, we got a set of couple rings which we could wear casually, this already gave me a rough idea of her ring size. If your better half wears rings already you can look at those for guidance on sizing too.

What about the design? Go for something special, something that might have some significance to both of you.

Jules and I are both huge fans of Disney’s Beauty and the Beast, in fact we love that movie so much that we even planned certain aspects of our wedding around it.

One of the key themes of Beauty and the Beast is the enchanted rose, so when I saw Gold Heart’s Celestial Astralle rose style ring; I fell in love with it.

As I was out with Jules one Sunday afternoon, I saw the poster for the ring next to a branch of Gold Heart. I pointed to it and said to Jules “Wow, that looks pretty cool huh”? She agreed and I said jokingly that we should go and see what something like that costs. We went over, she tried on a few sizes and then we left. I said it was just too expensive.

A month later, she asked me if we were going to look at rings again. I said we didn’t have the finances as we were still settling our holiday expenses. Two months passed, three months passed, before we knew it, a year had passed with no mention of the ring and no hint that I was planning to propose.

Little did she know, I had bought the very ring she had tried on that day a year ago. It wasn’t easy, but thanks to a few friends and contacts, I was able to get it!

That’s why Jules actually proclaims I had lied to her in our proposal video because she figured there would be no proposal coming for years! Haha!

So what about the rock? We all know that the notion of giving diamond engagement rings is something that was manufactured by the De Beers jewellery group years ago through clever marketing. It made people want to propose with a diamond engagement ring and of course prices subsequently skyrocketed. What this means, in essence, is that diamonds are nowhere near as precious as a lot of other stones. But the idea of a diamond engagement ring clicked with people, people liked it and that's why, to this day, diamonds remain the stone most people associate with proposals, romance and love.

When getting your rock, people go on about the 4Cs – Carat, Colour, Cut and Clarity.

Carat sizing refers to how big the diamond is and small increments in size equate to pretty huge increases in price.

For white diamonds, the colours are graded as shown in this chart.

Once a diamond is set in a ring, it assumes the colour of the metal the ring is made of. So the colour of the diamond isn’t as important as people think and only really noticeable when the stones are loose and side-by-side. Once the stone has been put into a ring, whether the diamond is colourless ‘D’ or near colourless ‘J’, you won’t be able to tell the difference! But it makes a huge difference to the overall cost.

Now unless your wife to be is a scientist and has her own microscope, then clarity is also something you may be able to sacrifice on when choosing your diamond. Tiny inclusion bodies, wisps and feathering simply aren’t visible to the naked human eye.

Some diamond brands state their stones have fancy cuts with a million more facets than other brands, claiming to sparkle and scintillate more in the light than other rocks. Diamond companies state that a small well cut diamond will sparkle more and be more visible from across the room as your glamorous fiancée comes down the stairs into the ball room compared to a giant but poorly cut diamond.

Most of the time this is fancy marketing but of course there are always exceptions, so go and see for yourself if the diamonds look more sparkly or not. Remember, the lighting in jewellery shops is specifically set up to make diamonds sparkle and look brighter so this may not reflect how the diamond will look in real life.

So that pretty much sums up all you need to know about diamond proposal rings! Of course you could always do something more unique and go for a sapphire, emerald, ruby or other precious stone.

Happy hunting!

5. The Bank Job

You don’t have to spend loads of money to plan a decent proposal!!!

It doesn’t have to be anything crazy, you don’t need to do a 10 million people flash mob proposal in Changi prison or whatever. You just need to do something from the heart, something that you think would be special for the two of you.

That means no damn HDB proposal (non-Singaporeans Google it)!!! And also no proposal planner!!!! If you can’t be bothered to plan your own proposal, the only thing that you will ever really need to plan to surprise the love of your life, then shame on you!

Remember it’s the thought that counts, so if you didn’t put any thought into it and let someone else do all the thinking and planning for you, then she probably won’t put a lot of thought into it when she answers your big question.

I proposed to Jules at Capella Hotel in Sentosa. We celebrated our first anniversary at Capella so it’s a place that has some special meaning for us.

I know what you must be thinking; it’s a really expensive hotel! But do you know how much it cost me?? Nothing! That’s right, I called Capella and said I wanted to propose to my girlfriend and asked if we could do it outside their bar with a view of the ocean and sunset, and guess what - they said yes!

In the end it wasn’t a huge extravaganza or anything, there weren’t thousands of people there, just the people that mattered to us.

6. The Proposal

Now it was time to set the wheels into motion.

I got my friend to set up a fake Facebook event page inviting Jules and I to a James Bond themed sunset cocktail party with our friends at Bob’s Bar (no affiliation =) at Capella. I even scripted what he should write for the event description. This was all just an excuse for me to wear a tuxedo and look smart when I proposed without having Jules suspect anything. Not bad eh =P

I was almost sabotaged on the actual day, as my friend who set up the Facebook event page wasn’t even in Singapore on the actual day! He was in the US and started checking into different locations – which would've been a dead giveaway seeing as he’s supposed to be hosting the party. Thankfully we managed to get him to take down his revealing check-ins before Jules saw anything! Phew!!

I knew how much Jules values her parents and family so it was important that they were there when I proposed. I knew that her family would also appreciate this, especially as they were not too happy when someone else in Juliana’s family had gotten engaged a short while before without informing anyone in the family. I didn’t want to make the same mistake, I wanted to do things right.

Next step was to plan my speech. I spent months rehearsing it in the shower or whenever I was alone. Make it count, make it touching, remind her of the good times, remind her how much she means to you and why you can't live without her! Then don't forget to get down on one knee. I even practiced doing this beforehand so I wouldn't fall over and make a fool of myself on the big day. Once in position, pop the question! =) If she says yes then place the engagement ring on her left hand ring finger (the finger next to the little finger). Then kiss her dummy! You don't need me to spell out everything! =P The date was quickly approaching.

As we pulled up to Capella in our taxi on the big day, I could see that we were being filmed. This was it, I was going to propose and I was nervous as hell!!

7. Picture Perfect

I know I’ve already said this but I can’t stress it enough, get someone to film or video your proposal. It will be over in the blink of an eye like these special moments always are but at least you will have something to look back at and laugh or maybe even cry.

I called in Juliana’s long time friend and colleague, Yong Thye. The guy is a genius, I told him what I wanted and he went way above and beyond my expectations.

He’s so good that we even brought him to Paris to make our fairytale wedding movie. The movie was deemed the most romantic fairytale wedding entrance video ever by popular Singapore website, Stomp:

Check it out:

And of course we simply couldn’t have anyone else as our actual day wedding videographer.

Thanks Yong Thye!!!

You can check out more of his work here:

8. The Princess Diaries 2: Royal Engagement

She said YES!!! =D

So there you go, this is how I planned my proposal. Hope you’ve enjoyed the ride as much as I have.

Good luck for your own proposal buddy! I wish you a blissful engagement and can’t wait to see your own proposal video soon =P

All you gotta do now is plan the wedding! Haha!!

I’d like to give a big shout-out to everyone who helped to make my dream proposal and wedding come true! Seb, Alice, Keeb, our brothers and sisters! We love you guys!

Signing off,

Dr. Bobby Stryker

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