The Complete Proposal Guide

The lights dim, cue dramatic music in background. The P R O P O S A L.

Whether you’re high school sweethearts, met through a friend, or swiped right on one another, you both found love and it’s time to take that next step in your relationship and make it forever. However figuring out how to propose is a massive undertaking, from buying the ring to planning what you’re going to say. Without further ado, here is your complete proposal guide from what to do to what to say to the love of your life.



  1.  Make Sure You’re on the Same PageWhile this might seem quite obvious, it is important to make sure you both have marriage in mind. Talk to your partner about your future together. Ask them if they see marriage in the future as well as letting them know that you’d like to be married one day. Will it be a hard conversation? Yes, but at the end of it, hopefully you’ll know what the answer is going to be when you open the box and show them a ring.
  2. Talk to their ParentsYes, I know this may be old school but this is still important. If your partner has hinted that you need to ask their parents for their hand in marriage, definitely do it! Otherwise, it would still be a good idea to let the parents know that marriage is on the horizon for both of you. It doesn’t have a to be a huge conversation, try saying something like this: “I am deeply in love with your son/daughter, and we want to spend our lives together. I am planning to propose, and want you to be involved in this exciting moment.”
  3. Buy the RingThe engagement ring is a piece of jewelry that your partner will likely wear for the rest of their life, so get a good sense of what they’ll really like to wear. Ask a close friend or family member to sneakily pick your partner’s brain about the type of engagement ring they’ll want. If you really have no idea, you could even go ring shopping together and have your partner pick out exactly what they want. As for where to get the ring, get some recommendations from family or friends to ensure that you’re buying from a trusted store with a great track record of service and quality. To find out your partner’s ring size, you could ask them or find a ring that they wear normally and bring it in with you to a jeweler to have it measured. If you get the size wrong, there’s always resizing!
  4. Figuring Out What to SayThe words that change both of your lives forever. Proposing is nerve-wracking, when you’re nervous, words are extra hard! I remember stumbling over my words, and my thoughts were all over the place. To help you get your  jumbled-up thoughts a little more sorted out, here are some questions to reflect on when thinking about what to say to the love of your life:
    What were your first impressions of them?Remember the first time you met. Think about what stuck out about them: was it something they did or how they looked, or a common interest that you both shared? Or maybe it was a hilarious moment, an accident. 

    When did you realize you loved them/wanted to spend the rest of your life with them?

    Was there a turning point in your relationship when you realized this? Did they come over and take care of you when you were sick or did they rather stay in and watch a movie when your fancy dinner plans fell through?


    How have they changed your life since you’ve met?

    Focus on the things that have improved now that they’re in your life. How have you grown as a person because of them? What have they taught you?


    How do they inspire you?

    In what ways do you admire them and aspire to be like them? You want to demonstrate that your love is not superficial and that it extends to their character as a person. 


    What values and goals do you share?

    Think about shared interests and values that are important to both of you, showing why you two do life so well together as a team. 


    What are your hopes and dreams for your future together?

    The engagement isn’t the end of an era for you two, but rather the beginning of a lifelong adventure. Where do you envision you and your future spouse in several years? What do you hope to continue or start doing with them?


  5. Personalize ItThink about the type of proposal that your partner will love. Will they enjoy being proposed to in a grand, public gesture, a private intimate moment for the just the two of you, or  a surprise surrounded by family and friends? When you’re thinking about where you want to propose, find a space that means something to them or for both of you. It could be the spot of your first date or your living room where you both said “I love you” for the first time. Regardless, make sure it’s personalized and significant for you both.
  6. CelebrateWhile you don’t need to have a full engagement party planned, have an idea for how you two will celebrate this special moment. You could have a romantic dinner for two planned, pop open a bottle of champagne, or have your close group of friends pop out from behind the bushes. Understand your partner’s personality to determine whether a private one-on-one celebration or full on engagement party would make them feel the most comfortable with celebrating this moment.
  7. Set Up a BackstoryTo avoid blowing the surprising, come up with a solid, foolproof backstory that throws your partner off track. Their intuition may give them a hint that something is up, especially if there’s a romantic dinner or an out-of-the-ordinary plans are made. A fake gameplan also helps you stay calm especially if you’re secure in this ruse that you made up.


Joanna & Brandon Chicago Lakefront Proposal



  1. Make Sure the Ring is HiddenNothing will ruin the proposal more than your partner seeing the shape of the ring box before you even think about getting on one knee. Make sure the box is hidden and not showing at all!
  2. Have a Photographer ReadyWhether you hire a photographer or you trust your friend with their iPhones, there’s nothing better than have this special moment documented. The captured surprised look on their face when you propose will be a story you can tell your all your family and friends. In this age where social media is king, I highly recommend hiring a professional photographer to get the best looking moment of your proposal. This can also double as a impromptu engagement session after you both catch your breaths and realize you’re engaged!
  3. Ask the QuestionYou know which question I’m talking. You’re down on one knee, take a deep breath, say the words that you rehearsed over and over again and ask the question.
  4. Savor the MomentYou did it! You asked the question, you put the ring on their finger. Hug it out, cry it out, collect yourselves and be in the moment. You’re officially engaged, have this moment together!


Thinking about having your proposal photographed? Contact me using the link below! I’d love to document this special moment for you and your fiancee.