Planning a proposal can be exciting, but it can also feel overwhelming. After helping couples plan surprise proposals throughout Chicago, I’ve seen a few common mistakes that can make the experience more stressful than it needs to be.

The good news is that most of them are completely avoidable. Here are five mistakes I encourage every client to avoid when planning their proposal.

1. Choosing a location without thinking about the crowd

It’s easy to fall in love with photos of Chicago’s most iconic proposal locations, but what many people don’t realize is that some of those spots can become incredibly busy depending on the day and time.

A beautiful location doesn’t always make for the best proposal if you’re surrounded by dozens of tourists, construction, or large events.

When planning a proposal, think about more than just the view. Consider privacy, foot traffic, and whether you’ll actually have space to enjoy the moment together.

One of my favorite parts of helping clients is recommending locations based not only on the scenery, but also on the overall experience they’re hoping to create.

2. Waiting until the last minute to plan

The best proposals rarely happen by accident.

Planning ahead gives you time to choose the right location, think through your timeline, and prepare for unexpected changes like weather or construction.

Even if you’re planning something simple, giving yourself a few weeks instead of a few days makes the process much less stressful.

3. Forgetting about lighting

Lighting can completely change the look and feel of your proposal photos.

Midday sunlight often creates harsh shadows, while golden hour provides softer, more flattering light. Cloudy days can also produce beautiful, even lighting.

You don’t need to become a photography expert, but choosing the right time of day can make a huge difference in your final gallery.

4. Trying to plan everything on your own

For many people, this is their first time planning a proposal.

There are a lot of little details to think about, including where to stand, how to keep the surprise, when to arrive, and what happens after your partner says yes.

Having someone help you think through those details can take a lot of pressure off your shoulders.

As your proposal photographer, my role starts well before the proposal itself. I help clients choose locations, coordinate logistics, and create a plan so they can focus on enjoying the moment instead of worrying about it.

5. Forgetting to be present

Once you get down on one knee, everything happens incredibly fast.

Many couples tell me afterward that the entire proposal felt like a blur.

That’s why preparing ahead of time is so valuable. When you’ve already thought through the details, you’re free to focus on your partner instead of wondering whether everything is going according to plan.

Those genuine reactions are often the moments you’ll treasure most.

A surprise proposal doesn’t have to be complicated, but a little preparation can make a big difference.

Whether you’re proposing along the Chicago Riverwalk, at Lincoln Park, by Lake Michigan, or somewhere that’s meaningful to your relationship, taking the time to plan ahead will help the experience feel more relaxed and memorable.

If you’re planning a surprise proposal in Chicago, I’d love to help you every step of the way. From choosing the perfect location to capturing the moment you hear “yes,” my goal is to make the process feel effortless so you can focus on what matters most.

Ready to start planning? You can learn more about my Chicago proposal photography experience or get in touch through my contact page.