Kristina Staal 


November 7, 2018

How to Plan the Perfect Proposal


At some point, every girl thinks about their wedding proposal in some way or another, and although I’m not a guy, I’m pretty sure this must be true for a good amount of guys too! I know for myself, I thought about who I would marry and what my proposal and wedding would be like from the time that I was a little girl. So, I think it’s fair to say that a wedding proposal is one of the most special and memorable moments of a couple’s life. I know mine is for sure! But, we’ll save the story of how Nick proposed to me for another day.

Today I’m talking about what to take into consideration when proposing to your future wife (or husband!). My younger brother (Chris) recently proposed and married his wife (Michelle), and I was over-the-moon with excitement to help him plan out his proposal.

We had so much fun planning his proposal, so I thought I would share tips of what to think of when planning your proposal. And of course, I had to include images of my brothers proposal, which I was beyond honoured to capture, while my dad captured drone video and images from above. (Clearly it was a family team effort – my mom even helped my brother search high and low for the best engagement ring, and Nick was the assistant drone photographer to my dad). It was quite the surprise, and I think Michelle’s face says it all!

Proposal Tips


  1. Hire a photographer!

As a photographer, I may be a bit biased, but I think it’s fair to say that no-one ever regrets having pictures of a really special moment in their life, right? When searching for your photographer, make sure to check their portfolio to ensure you like their style, plan a time to talk to ensure you get along well and that they’re comfortable photographing a proposal, and come up with a solid plan to keep the proposal top-secret!

My brother and I planned his proposal over the course of a few months, everything from how we would get Michelle to Montauk (we told her I needed a couple to photograph for a styled shoot and she totally believed it), to the floral crown he wanted me to make her, to what she felt comfortable wearing for photos (at the end of the day, this was all about her, and we wanted her to feel beautiful, special and comfortable in one of her favourite dresses), to the small details of what we would include, such as the picnic basket and wine that my brother brought to celebrate afterwards. And, after a lot of research about Montauk, we came up with an exact location, timeline and breakdown of how and when my brother would propose.

Tip: Have a secret signal between you and your photographer to let them know that you’re about to propose! If your photographer is hiding and secretly photographing you, this could be a bit more tricky, so definitely talk it over with them first.

2. Pick a Memorable Location

Remember, where you propose is going to be somewhere that will be forever sentimental. Is it somewhere you travel that has a close place in your heart? Maybe, the first place you both met? Or, maybe you want it somewhere close by so that you can go back to celebrate your anniversary every year. Wherever the location is, make sure to give it thought and meaning! And, it always helps to have a beautiful and romantic location. You also may want to take into consideration if your significant other would prefer a a proposal in a private or public setting. Proposals can be intimate, so it’s definitely something to think of.

3. What You’ll Say 

Probably the most important part of the proposal is what you’ll say. (Aside from your significant other saying YES!) When you propose, make sure to talk about why you love your significant other and how they complete you. Sharing your feelings is a great way to start off the next chapter of your relationship! Plus, who doesn’t love hearing that their loved and cared for?!


4.  The Ring

Make sure to have your ring tucked away somewhere that won’t be seen. And, make sure to be careful when you pull it out! Especially if you’re proposing near a body of water, or somewhere that the ring can be easily lost if dropped. Having it in a ring box, and making sure that you open it the right way up, definitely helps. And, if you’re looking for the most adorable ring box, make sure to check out The Mrs. Box.


5. Plan Something for after the Proposal! 

Now that you’re engaged, it’s time to celebrate! Make sure to plan something special and meaningful for after your proposal. It can be as simple as a special meal you’ve cooked and your favourite movie by the fire. Or, having a private dinner cooked for you at a restaurant or even setting sail on a sailboat to celebrate. As long as how you propose has special meaning to you and fiancee, that’s all that matters. And, if you’re wanting to start off your engagement and wedding planning with a little something special, Elmo Paper Stories has the most adorable Bride Planning Journals!

If you have any additional proposal tips, we’d love to hear! Please comment below.

You can also check out Chris & Michelle’s proposal on:

How He Asked

Wedding Lovely Blog



Drone Photographer: Andrew Tomaszewski

Assistant Drone Photographer: Nicholas Staal

Floral crown by Kristina Staal

Photographed in Montauk, New York


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