How To Plan The Perfect Proposal

How To Plan The Perfect Proposal | Chicago proposal

It’s that time of year. Subtle trips to the jewelry store to “try on rings”, and your favorite rom-com Hallmark movies playing on repeat. Tis’ the season for proposals and I am here to make sure that anybody and everybody who is planning to get engaged knows how to plan the perfect proposal.

Now I know what you’re probably thinking… “how hard can it be?”. The answer is? Very. Especially if you’re wanting that *picture-perfect* fairytale-like moment. Proposals can take a lot of time, effort, brainstorming, and planning. Lucky for you though, I’ve condensed all of my experience with helping plan proposals to the absolute necessities.

Engagement Ring Shopping – Chicago Jewelry Stores

Okay, so obviously the key component of a completely beautiful, romantic, and EPIC proposal is of course… the engagement ring. While there are hundreds of thousands of places you can purchase that perfect ring for your partner, here are just a few Chicago jewelry stores that may capture your eye.

Make sure to consider where you’re buying your engagement ring from and whether or not you’re able to support a small business when finding your dream ring! Shop local and shop small if you can.

You’ll also need to decide what kind of diamond/stone you’re looking for. Are you looking for a natural diamond? Moissanite or lab-grown? Non-diamond? All of these things are factors to consider in the ethical and sustainable choice of your partner’s engagement ring.

Most jewelers will recommend starting shopping for the perfect ring about 3 months before you plan to propose. That way there’s time to have the ring sized properly, make any adjustments needed, and be ready to go for when the big moment arrives!

Here are a few local Chicago jewelry stores to consider to support a small business:

  1. Plum Diamonds: One of the founders, Kristy, is as sweet as pie! They create beautiful work and is a member of the Green Wedding Alliance, a wedding sustainability-focused community.
  2. Mineralogy: Perfect for the person wanting an engagement ring as unique as they are. Women and minority-owned in Chicago!
  3. Ivy & Rose: Another local Chicago shop, this is perfect for the person looking for a unique vintage-inspired band.
  4. Windy City Diamonds: a Chicago classic passed down through four generations of Chicagoans.

Here are a few national chains that have showrooms in Chicago for you to peruse:

  1. VRAI: specializing in lab-grown diamonds, this company is all about conflict-free and sustainable jewelry. All of their diamonds are grown via 100% hydropower in their zero-emission foundry in the Pacific Northwest. (my engagement ring is from here!)
  2. Brilliant Earth: From detailed natural diamond source tracking, to recycled metals, and finally to both ethical natural and lab-grown options, Brilliant Earth is another great choice with a Chicago showroom!

Steps to Plan The Perfect Proposal

Now that you’ve gotten your boo the perfect ring for your proposal, it’s time to plan. These are the key fundamental elements to knowing how to plan the perfect proposal.

1. Hire A Photographer To Capture The Moment

Am I biased if I say that one of the most important aspects of knowing how to plan the perfect proposal is making sure you hire a photographer to capture the moment? Maybe. However, I will scream it from the mountain tops! This is a huge life-changing moment and it should be cherished and documented.

After you get engaged, be prepared to hear a flood of questions and congratulations. With that, you want to be able to detail every moment of your proposal! This can be difficult especially when you are dealing with so many feelings in one moment. Every tear, laugh, and smile is a moment worth documenting. So I highly recommend you don’t skimp out on this step. P.s… I photograph proposals *cough cough*.

2. Consider What Fits You Two Best

How To Plan The Perfect Proposal | Chicago proposal

Next, you want to figure out the where. That’s kind of important, ya know? When deciding on the location for your proposal, consider what fits both of you and what you both enjoy. Do you want to propose in public? What about somewhere more private? Or choose a location that means something to your love story? These are some of the questions that can and should run through your mind when knowing how to plan the perfect proposal.

When choosing a location for your proposal, consider what your soon-to-be fiancé would want. If they’re more of a private person, maybe not opt to propose in a busy park or restaurant. Instead, choose a more quiet and secluded area or even propose within the comforts of your own home. Oh, and if you’re already wondering about how your photographer would play into all this, don’t worry. We are masters of disguise, just about anywhere.

3. Set The Scene

Okay so you’ve got the ring, the photographer and the location picked out… now what? You want to make sure that you are setting the scene for your proposal! How do you envision setting up this moment? Are you wanting something more subtle and subdued, or go all out and extravagant? Do you envision you and your partner with a large setup, photos, and candles laid out with a sign that says “marry me”?

Maybe you’re someone who would much rather go the simpler route where it’s more about being in the moment, just the two of you. No extra fluff. Well, guess what? That’s fine too! Whichever option you choose, just make sure you do it with intentionality and of course, thinking about your partner’s needs as well.

4. How To Pop The Question

When it comes to actually popping the question, there are two different ways you can go about it.

Option 1: Book your proposal with a photographer and have the photographer direct the moment. This is helpful if you’re needing a bit more guidance and support when it comes to asking that important question. In this scenario, you’ll want to book the session under the disguise of an anniversary session, needing photos for your holiday card, or you can ask your photographer to reach out for you two to “model” for a styled couples session so it seems less suspicious. 😉

You’ll start the session taking normal portraits and at the designated time, your photographer will guide you and your partner with prompts such as telling you, the couple, to stand back to back. Then the person proposing turns around and is magically down on one knee when the other person turns around for the big surprise moment!

Option 2: I touched on this briefly before, but your photographer can also be hidden away to capture surprise photos of the moment as it happens. This is better for someone who wants to keep the moment more of a surprise and needs a little bit less guidance when it comes to how to pop the question.

Either way, we’ll work together to determine the best course of action for your specific proposal. We’ll hop on the phone leading up to your day so that you feel completely confident walking into your proposal so that it will go off without a hitch!

5. Best Tips For A Smooth Proposal

Whichever way you choose to pop the question, you’ll likely still feel a little nervous when the moment finally arrives. Here are three things to remember when you start feeling the butterflies:

  • Try to soak in every moment that you can. This is a life-changing question and you’re going to want to remember the moment forever. Take a few deep breaths and do your best to take as many mental pictures as you can. And for what you forget in the chaos of the moment? That’s what I’m there for 🙂
  • Make sure to stay down on one knee (if you choose to propose that way) for at least a few seconds! That way there’s plenty of time to capture that all-important moment!
  • What bags/items do you have with you? Make sure that if you want to discard your backpack/purse so your hands are free for the proposal, you drop it out of the way of your photos. Nothing ruins a beautiful proposal photo faster than a lump of a bag blocking the view of the big moment! If you can help it, try not to bring any more items than you need.

6. Do You Have An Audience?

This ties into what location you choose to pop the question at, but think about who is around during the big moment. Do you want it to just be you and your photographer? Or are you someone who is wanting family and friends around to join in on the moment? During this type of decision-making, consider what your partner may want. Some may prefer to have friends and family around during such a special and life-changing moment. Others, on the other hand, may prefer to keep this moment more private and meet up with friends and family later on to celebrate.

In my experience, it’s usually best to leave the moment just for the two of you to enjoy. Take 10-15 minutes for some photos to document this moment (and also process what just happened) before meeting your friends and family after the proposal. That way you’re still getting that privacy and intimacy with your partner, but are able to celebrate with those who are near and dear to you.

7. The Proposal Aftermath

Everyone gets so caught up with the actual proposal itself, that they seem to neglect one thing. The proposal aftermath aka, what happens next?! Your engagement does not just have to stop at the proposal. In fact, I encourage it not to and to fully take advantage of this moment!

Use this moment to book a nice dinner reservation, have some friends and family gather for a surprise engagement party, or get your favorite take-out and cuddle up and watch a movie at home. Don’t let the day fizzle out after the infamous “will you marry me?”. Soak up this moment and enjoy every second of it.

How To Plan The Perfect Proposal

So whether you’re looking to go all out for your proposal or something a bit more casual, the most important thing is that it feels right to you and your partner. Knowing how to plan the perfect proposal is only half the battle.

Now, you have to gear up, get ready, drop to one knee, and actually do it! For all you future fiancés out there – congratulations!

Don’t forget that these moments deserve to be documented so if you’re in the need to hire a photographer for this special moment, I’m your gal! Click here to fill out my inquiry form and let’s start planning!

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