The “How To Propose In Chicago” Guide

So if you’re reading this, you’re probably nervous as all HELL and wanting to make sure your city proposal is everything your significant other deserves and MORE! I got you…here is my official How To Propose in Chicago Guide for all those wanting everything to go off without a hitch and to make memories that last a lifetime! 🙂

Location, Location, Location

When thinking about how to propose, your location is one of the first things that comes to mind. This is going to be the backdrop for your special moment! One of the most important things to consider when choosing a spot is the amount of foot traffic. Would you rather pop the question in a secluded place where you two can be alone? Or a public area? Making sure you’re aware of how busy the location is will save you from getting photos that have a bunch of strangers in the background. If it’s a restaurant, make sure you know if they are strict about photography, so call ahead and ask, some may require a photo fee.  

Time It Right

The time of year and time of day is something to keep in the back of your mind when figuring out how to propose. Do you want the sun shining or do you want a romantic sunset vibe? Do you want city vies like at North Ave Beach or more nature as the background like near Lincoln Park Board walk? Or are you two more of the indoorsy, and enjoy a good cuddle on the couch with some wine?

Hire A Photographer

In my opinion it’s better to lock down a photographer than regret later on not having that special moment captured. The best part about having a photographer is that we can give you real, personalized tips on how to propose and make it unique to you. I absolutely adore helping my couples plan the entire thing and make sure everything is executed to perfection. Best of all, I have a 48-72 hour turnaround time, so you can have them immediately to post and share with your friends and family!

Catch Them Off Guard or Leave Them Hints?

Some people LOVE being surprised… other’s get too anxious. It’s important to know your sweetie and understand what they would want in this situation! If they love surprises and want to be completely caught off guard, it’s helpful to keep things “natural” and do things you would do together normally – until the actual big moment! If you two have talked about it before and you’d rather leave them subtle hints throughout the day to help them mentally prepare for the moment, you can set up a whole day of extravagant dates or experiences to lead up to the proposal. Knowing how to propose for YOUR partner is key! 😉  

Dropping The Knee

When you’re thinking about how to propose, you’re probably thinking about the exact moment a lot. What will you say..? What knee will you use…? The most important thing is hanging out on that knee longer than you want to and speaking from the heart! If you have a speech prepared, more often than not you may forget it and that’s okay! Just tell them how much you love them and wanna spend your life together. Let them come to you to kiss you first, then you can stand up – this makes sure I can snap that moment perfectly!

Bring The Fam 

Think about whether or not you want friends or family to meet you after you’ve popped the question! It can be so much fun to celebrate that exciting moment with a mini engagement party. Either having your families pop out at the location, so they can all witness or having them meet you out afterwards for drinks! It’s always such a nice way to remember how much you’re both loved and supported. 

At the end of the day, your partner just wants to share a special day with you. Even if you forget everything you know about how to propose and all hell breaks loose, it will make for an AMAZING story 😉 Just remember… be yourself and have fun. AND take me with you! 

What now? If you want to know what happens next after the proposal and into being engaged, read my blog to see my ultimate to-do list for when you first get engaged! 



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I know planning your dream wedding can be stressful, heres the thing though, you don't have to do this alone!! I got you! I will be your Chicago wedding guide helping you navigate the not so fun parts of planning your best day ever! I believe you should have FUN on your wedding day! I know, crazy right? Let me prove it to you! 

I'm Victoria! Hello and welcome to the blog!

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