All the tips for planning your proposal

So you’re ready to pop the question- YAY! Whether you’re dreaming of an epic ocean view moment or something quiet and sentimental just for the two of you, planning a proposal is such an exciting (and nerve-wracking!) step. I'll be here to ensure that every reaction, every laugh, and that all-important YES is captured forever.


If you’re planning to propose in Rhode Island, Massachusetts, or beyond, this guide will walk you through everything you need to know to make it perfect.

Choosing the location

The perfect spot!

The location sets the entire vibe of your proposal. Think about what feels most like you two—this is the place you’ll always remember, so make it meaningful. If you already have a spot in mind that's amazing and if not, I have a blog post filled with some of my favorite spots to help you find the perfect spot.

Consider these things with your location:

Think about if you want it to be at a scenic spot like the Boston city skyline, or a classic Newport lighthouse, or if you want it to be a sentimental spot instead! Somewhere like where you had your first date, your favorite weekend spot or something fun like a scavenger hunt! If you are planning to be somewhere new and out in public, keep in mind that there will most likely be other people around and I will do my best to clear the area or spot ahead of time but you may get some strangers cheering and congratulating you. Think about how accessible it is to get there, is it a hike or a far walk? Make sure you are both dressed for the setting, nobody likes to hike in heels when they didn't expect it!

How to Get Your Partner to the Proposal Spot (Without Giving It Away)

A big part of planning a surprise proposal is figuring out how to get your partner to the right place at the right time—without giving the whole thing away! A tip I have is to consider what excuse you’ll use to get your partner there. A “sunset walk on the beach” or “early coffee date in the park” feels natural without raising suspicion, especially if this is something you’d already do together. Maybe you plan a day out with friends and throw your partner off your trail by having an “alibi,” then sneak away and pop up at the proposal spot as the big surprise.


Here are a few other fun ways to make it work:

Disguise it as a photoshoot – Get your partner to do an anniversary photoshoot or a family photoshoot and I will tell you ahead of time the right prompt for you to get down on one knee and ask the question!

Celebration in disguise – Tell them you’re going to celebrate a birthday, job promotion, or holiday dinner—then lead them to the real surprise.

Adventure excuse – Plan a hike, picnic, or day trip somewhere scenic.

Friend/family setup – Have friends or family invite you both to “meet them” at a location, but instead, it’s your proposal waiting.

Date night twist – My go-to and all time favorite! A “nice dinner reservation” that just happens to start with a walk through a park or city square where the proposal happens.


The key is to keep it natural and believable. Think of what your partner would say “yes” to without hesitation, so the surprise feels effortless. We’ll work together to make sure it’s smooth, stress-free, and perfectly timed.

Planning the Details

The magic of a proposal is in the details that make it personal. Big or small, it’s those little touches that will make the moment unforgettable.


Some ideas to make it yours:

Music:A playlist of your favorite songs quietly playing in the background.

Props: A blanket, champagne, flowers, a picnic set up with a sign, or even your dog wearing a “Will you marry me?” bandana.

Words: Write a letter to read before you propose, or plan a few things you want to say and try and practice this beforehand!!

Decor: A small picnic setup, candles, or florals can elevate the scene (and give me more fun details to capture!).


Decide if you want it to be a true surprise or if you’ll drop hints ahead of time. Some people love being completely caught off-guard, while others prefer a little mental prep so they’re dressed and feeling good for photos.

 

Be Prepared


Consider the Logistics

This is where proposals can get tricky—and where having a photographer helps so much. Think through:

  • Crowds – Will people be around? Do you care if strangers clapping when it happens, or would you rather have a tucked-away corner?
  • Weather – We can plan for a backup option although it may be hard depending on other details but I will work with you on this!
  • Ring Safety – Sounds obvious, but don’t keep the ring loose in your pocket. A small ring box or even a slimmer “proposal box” helps keep things smooth- and so that you don't have an obvious ring box shaped lump in your pocket ;)
  • Positioning – Believe it or not, even how you kneel matters., try and be strong and have a good form with your knee at 90 degrees and you should try not to hunch over.  We’ll plan so that when you drop down, your partner’s face (and their reaction!) is visible to me, not hidden.

 

How I will Help

Your only job is to focus on asking the question. I’ll handle the rest. Here’s how it usually works:

Planning Call – We’ll chat about your vision, location, timing, and any personal details you want included. We will go through the plan together and also look at the location through Google Maps so we are prepped. We will also discuss if you want me to announce myself ahead of time and give you a cue or if you want me to blend in.


The Proposal Day –We will be sharing locations with each other and I will let you know when I'm on my way and I’ll be there early, in position, blending in until it’s time.


Post-Proposal Portraits – Once the “yes!” is said and hugs are had, we’ll take a few just-engaged photos while emotions are fresh. I'll guide you through posing and help you feel comfortable.


Pro tip: You can take a selfie with each other and ask me to take a photo of the two of you together then I will prompt you to get down on one knee and pop the question!

Your Outfits & Look

You want to look nice while still feeling comfortable and confident in your outfits. Try to make sure that your outfit complements your partner's. You don't want to clash or look like you're wearing completely different styles.


Coordinate your colors and styles so that you look like a cohesive unit. Keep the word complement in mind rather than match. Think of color families and color palettes as well, there are great ideas on Pinterest I have saved here! I have another blog post that goes in depth on how to find your perfect engagement shoot outfit you can check out here.

More Outfit Tips

  • Avoid, big bold patterns
  • Avoid bright, neon colors
  • Wear simple hats and accessories
  • Try, neutral and muted colors
  • Wear different textures

COLORS THE CAMERA LOVES

  • White
  • Black
  • Beige
  • Stone & Navy Blue
  • Sage/ Forest Green

 

Posing

After you've popped the question and had a moment to soak it in, I will take a few fun photos with the two of you to celebrate your engagement! My priority is for you to feel confident and comfortable at all times! I have a variety of poses I use for every engagement session.


If I tell you to do something that feels a little funny, it’s probably because I know it’s going to make the two of you laugh - and that’s the photo I'm actually looking for. The weirder it feels the better it usually looks!


I'll do my best to keep an eye on your hair, makeup, and outfits to make sure things stay in place. I want you to feel as relaxed as possible and enjoy your time together!

 

What about Weather?

I am always checking the weather app leading up to our session. I have shot a proposal when it started to drizzle and it was magic! If the forecast for the day looks iffy leading up to the session we will plan for a backup option or even reschedule if we can.

after the session- getting your photos

After our session, I'll go home and edit all of the beautiful photos!

I will send over some sneak peeks within 24 hours after the proposal so you can share with friends and family! The final gallery can take anywhere from 2-4 weeks and you'll get your gallery through a online link via email where you will get a step-by-step process on how you should download your photos and access to my print shop linked to your gallery.

To keep your photos forever, I recommend downloading them through the Google Photos option on my site! Keep in mind I will archive galleries as time goes by so please download your photos ASAP, I'll give you a warning email when your gallery will be archived.

After the session


Please don't alter your photos in any way ( filters, face tune, etc) If there is a problem, let me know ASAP and I can do my best to help figure it out! Keep in mind this is in the contract that you signed!

photoshop requests


I can photoshop unwanted objects out of photos, acne, etc. I can't make you into Bella Hadid or a Kardashian, I'm here to capture the REAL you!

social media


Please tag me in any social media posts afterward! @kaitlynchabotphoto Social media and referrals are a photographer's best friend and help so much! ( plus I want to hype you up!)

 

Ready to Plan Your Proposal?

This is the start of something amazing, and I’d love to be part of it. Whether you’re planning to propose by the ocean, in the city, or somewhere totally unexpected, I’ll be there to capture every second. Reach out to me using my link here.

You bring the love. I’ll bring the camera. 💍