Five tips to help you pop the question

Planning how you’re going to pop the question is a bloody nightmare for any bloke. Where am I going to propose? How am I going to begin thinking about buying a ring? How am I going to find out her ring size without completely blowing my cover? When I buy the ring, how am I going to hide it from her (particularly as most guys pop the question on holiday, so this means keeping it a secret whilst packing, catching a flight, unpacking, and in the days in a small hotel room leading up to asking her to marry you)? I grew a few grey hairs during the engagement process, let me tell you.

Anyway, for the lads out there who are planning on proposing to their [hopefully] soon-to-be fiancée – here is how to propose.

1. Ask early about the ring size

I asked Chloe for her ring size fairly early on in our relationship. I did so, of course, because I was sure that at some point in our relationship I was going to ask her to marry me. What this did was enable me to find Chloe’s exact ring size, without messing around with sketchy tactics such as trying to ask her friend(s) to take her to a jewellers to get measurements of her wedding ring finger, which would be beyond obvious in itself. Chloe doesn’t wear much jewellery, which I like, so I didn’t have the luxury of using a ring she already has as a guide. By asking Chloe directly early on, I was still able to keep the element of surprise – as it was about nine months later that I proposed – but also have complete confidence that I had the right size and know that I hadn’t used gimmicks closer to the time of the engagement, which had the potential to blow my cover.

2. Research a good jeweller

Thankfully Chloe and I have similar tastes and I was confident of what I was getting her. This, I am sure, isn’t the case for all guys. A great way to get around this problem is by selecting a jewellers who help you design the ring. I always thought it’d be like the movies in that you’d go to a store on the highstreet and pick up a ring from the shelf. But it isn’t. You usually have a meeting with a jeweller who’ll ask you questions, talk through designs, and workshop a ring for you. You then pay a deposit and the ring takes around five weeks to make. In deciding which jewellers to choose, do your research to see which are highly rated specifically for engagement rings. I bought mine from Larsen Jewellery in Melbourne and they were absolutely fantastic.

3. Be stealthy

What a bloody nightmare keeping it a secret is! We lived in a small apartment in Melbourne’s CBD and when I went to collect the ring Chloe was chilling at home. So, as you can imagine, I spent the entirety of the walk to collect the ring, time inspecting and purchasing the ring, and the walk home panicking as to how I’d get it passed her. Anyway, thankfully me putting it in my jacket pocket and resting it over my arm for extra stealth – did the trick. Hiding it over the next couple of weeks was fairly easy (in the back of a drawer), but hiding it in my suitcase as we packed to go to Rarotonga was taxing on the old blood pressure. I hid it in my shaving bag, which I put in the netted zip-up pocket inside my suitcase. To me, this wasn’t subtle at all, but thankfully she didn’t notice. The ring sat in my suitcase in the same place until I popped the question a few days later.

How to propose – 5 tips to help you pop the question
I found a location I knew she would love.


4. Pick a location right for you

This really is personal to the couple. I arranged for a candlelit dinner at The Rarotongan – a resort in the beautiful Cook Islands – which I had organised in the weeks leading up to it in Melbourne. The Cook Islands was a destination which Chloe and I had always dreamt of visiting, and as Chloe loves beaches and taking amazing photos – I wanted to make sure the location of the proposal ticked those boxes. While we weren’t staying at The Rarotongan, most resorts will enable you to purchase their premium offerings if you aren’t a guest – so that worked in my favour. When we arrived, there was a bit of whispering and giggling amongst the staff, which was sweet as I had been dealing with them via email over the previous weeks and they knew I was proposing. We were then escorted along the beach to our own private gazebo, which had been decorated with white linen with a table in the middle. We sat and had a five course meal. I proposed after the starter.

5. Prepare for some awkwardness

Not gonna lie, the proposal can get awkward. You literally have no chat in the moments prior to asking her to marry you, because it is literally the ONLY thing on your mind. I think I said things like, “the sand is nice” about three times, and “what a great resort” numerous times as well. I had nothing. Anyway, after 5 minutes of awkwardness and me repeating myself, Chloe went to the toilet (who could blame her!). This was my golden opportunity. I grabbed the ring that was in my bag and put it underneath my napkin in between my legs. When Chloe came back, she sat down and I said, “so there’s a reason I brought you here…”.

I asked, she said “of course”, and that was followed by lots of happy tears. Job done.

We get married in February 2020.

Read more about our love story here.

How to propose – 5 tips to help you pop the question
She said “yes”.