A man proposes to his partner on one knee in Stonington, Connecticut

Planning the Perfect Proposal

Proposing is a big deal, maybe one of the biggest! When I did it, I wish I’d had some kind of direction or advice. Most guides that I’ve seen are written from the standpoints of money, relationship strength, or are based on gender norms. Honestly, I don’t really think people need more advice on how to figure that stuff out.

Therefore, I’ve decided to approach this topic from the standpoint of practical planning, focusing on the How and When first and foremost. Then I got to thinking: where do people propose in Connecticut? The Where of planning your proposal may come first in priority, or last. It all depends!

The following is a practical guide for how to plan a proposal, up to and including thoughts on proposal photos. Here is a rough outline for how to propose as well as places to propose in Connecticut.

Quick Summary: How to Propose

When deciding to propose and considering how to about planning a proposal, here are the things to think about:

  1. Finalize and be confident in your decision

    Forget about the concept of “the one” and focus on whether or not you’re ready to spend the rest of your life with your partner.

  2. Make a ring decision

    Though most people propose with a ring, but that’s not necessarily required. If you’ll be getting one, there are decisions to be made.

  3. Make arrangements

    From the ground up, build your proposal plan. This includes the How, Where, and When details.

  4. Write a marriage proposal script

    Yes, you’re a writer at this point. Write down what you’ll say to your partner when you pop the question.

  5. Decide on whether or not to have your proposal photographed

    Whether you’re hiring a photographer or taking the DIY approach, make a decision on how to capture your proposal photos.

  6. Practice, practice, practice

    Rehearse your proposal.

  7. Stay calm

    Water and oxygen help with this!

  8. Keep it to yourself as much as possible

    The old adage “loose lips sink ships” comes to mind. Unless there’s someone intricately involved in your proposal, don’t tell anyone.

Detailed Steps for Planning Your Proposal

Now for the meat and potatoes. Let’s get into how to plan a proposal.

1. Finalize Your Decision and Be Confident

For the purposes of this guide, let’s assume that you’re mostly ready to propose. Naturally then, you should  probably get just about all the way there as a first step! This was my first step in planning to propose, knowing that I was actually ready to do so. 

You’ll want to do some soul-searching here, making sure that you’re ready to be a spouse and that your partner is the one you’d like to bestow that prize upon. By the way, there are even interviews out there where people explain how they knew it was time to plan a proposal.

2. Decide on a Ring (or Not)

Connecticut proposal photo of a newly engaged couple.

According to the American Gem Society, the first person to plan a proposal with an engagement ring was an Austrian duke. This sparked the tradition in Europe during the 15th century. 

Although most marriage proposals involve an engagement ring purchase beforehand, not all do by any means. This is a personal thing between you and your partner: perhaps they’ve made it clear to you that they don’t want an engagement ring or that they’d like to have a family heirloom ring

Naturally then, when approaching how to propose, read the room and make a decision on whether or not you’ll be proposing with a ring, then go get it (or not).

Be discrete obtaining their engagement ring size

The issue of what size of engagement ring to get when planning your proposal is a big one. I was lucky: my wife wore rings before we got engaged, so I was able to take one, compare it to a measuring guide, and go from there. The more popular ring metals (i.e. silver, gold, and platinum) can be easily resized as long as the design of the ring allows for it. Be sure to inquire with your jeweler about how they handle resizing (expecting at least one complimentary resizing is reasonable).

Learn the basics of engagement rings

The retail diamond industry is a big behemoth and navigating engagement ring decisions can be a huge pain. What I don’t recommend you do is just walk into a jewelry store and say, “I’m looking for an engagement ring.” Would you ever walk onto a used car lot and just ask for a car? Probably not, so try and educate yourself on engagement rings before you buy. 

Let me try and break it down as simply as possible, then from here you can look into it further:

  1. Ring metals: Maybe start here. If your partner has never expressed anything about their preferred ring metal, just know that the two most popular types are probably yellow gold and white gold. Others include platinum, sterling silver, and rose gold. If you’ve never noticed your partner’s jewelry habits, now’s the time to look into them.
  2. Ring types/settings: Does your partner prefer the classic look of a solitaire setting or the elegant bling of a pavé ring? The different types, or settings, of engagement rings bring about another decision that you’ll need to make. Again, with nothing to go on from your partner, you’ll end up comparing and contrasting based on what you know about their personality (i.e. the more stones, the more attention).
  3. Ring stones: Of course, the classic, tried and true choice is a diamond. But some people may consider diamonds to be played out and there definitely can be some controversy surrounding how they are mined and sold. If you’ll be going the diamond route, read up on the basics of “the four Cs” and familiarize yourself with how to balance them within your budget. Should you elect, either through your partner’s wishes or your own decision, to go another stone route, great! There are plenty of other engagement stone options.
  4. Eventual match with a wedding band: Now here’s one you may not have thought of: the eventual wedding band that your partner may wear with their engagement ring. Again, this is another tradition that not everyone practices. But if it’s in the cards for your eventual spouse-to-be, keep it in mind. The literal side-by-side fit of your partner’s two rings is an issue to consider. This ring-matching tool by Jared illustrates the idea.

Connecticut engagement ring jewelers

Here are a few engagement ring jewelers here in Connecticut that my wedding couples have used recently:

  1. Rumanof’s Fine Jewelry (Hamden, CT)
  2. Christie’s Fine Jewelry (Manchester, CT)
  3. Hannoush Jewelers (Waterford, CT)
  4. Mallove’s Jewelers (Mystic, CT)

If you’re an online shopper, I had an absolutely great experience with James Allen.

3. Make Arrangements for the Proposal

Once you’ve laid the foundation of your decision to propose, it’ll be time to start building up from there. This is actually quite intuitive, but can be a little stressful. Let’s break it down:

How: Pretend you’re writing a movie

If practical, I recommend starting with How you’re going to propose. Has your partner ever expressed something like, “I’ve always pictured you proposing like this…” and are you on board with that? Have they ever dropped other subtle hints? Will you instead have full creative control? Literally pretend that you’re writing a movie here as you consider how to plan your proposal. Later, we’ll get to actually writing a script. 

And no, not everyone gets down on one knee these days. Anyone who tells you that this is central to how to plan a proposal is being a little disingenuous.

Where: Your proposal location is key

Proposing is like real estate in this regard: location, location, location. You two will always remember where you got engaged, so make sure that you put some real thought into this part. If you’re in my area, be sure to read on in this post for some great Connecticut proposal location ideas.

When: The date and time matter, too

After How and Where, I think the last big piece is planning When to propose. Again, I’d say you should start by thinking about any of your partner’s wishes and desires that they’ve expressed to you. For example, have they said that a fall proposal is a must? Remember, however, that your engagement is about both of you!

In addition to the season, there are other timing factors in play when you try to plan your proposal. Is there a time of day that is of any significance? A specific day of the week maybe? Perhaps most importantly, does your proposal’s How factor into when you’re going to propose?

Bring it all together

Before we move on to what to say when proposing, try bringing together the How, Where, and When of your specific instance of how to propose. Make sure it all looks great to you, then ask yourself how you envision your partner feeling.

4. Decide What to Say When You Propose

You’ve made it this far! The next step in how to plan a proposal is determining what to actually say when you propose. I do not recommend winging this; if you’re human, you’ll be nervous when you pop the question. You don’t want to be fumbling around for words in the moment. You’ve planned everything else about your proposal, why not give some thought to what to say?

What to say when you propose is a big deal! And yes, actually writing your script is a great to perfect this part. Break out a pen and pad, or your Notes app, and actually write stuff down.

The Intro: Start off naturally

In your planning process, after completing step 3 of how to propose, you’ll need to mentally place yourself in the scenario you’ve created. For the purposes of your script, take the How, Where, and When of planning your proposal and start there. As an example:

  • How: Down on one knee because your partner is traditional in that way and you’re good with it
  • Where: Harkness Memorial State Park in Waterford, CT, the location of your fourth ever date together
  • When: Sunset on such-and-such date in the spring because your partner loves springtime and sunsets

So, combining all of that, your proposal script might start off very simply like this, slated to be spoken as you’re walking down the boardwalk to the sand at Harkness:

“Remember when we came on that date here? I could really tell that you were in love with my charm, smile, and overall aura even that early on. It was really clear in your eyes…”

Cheesy? Yes, it was meant to be. But hopefully you get the idea: tie your past as a couple to the present of your proposal, but don’t reveal the proposal yet.

The Body: Lead into why you’re there

This part is a little easier and clearer. Leave room in your script to allow the conversation to flow naturally. One way to do this is to just be quiet and let your unsuspecting partner talk, hopefully expressing how happy they are that you planned this new “date” for the two of you. You can prepare yourself to respond to what they say, gradually building towards the big reveal. Here’s an example:

Partner: [says anything]

You: “We’ve been talking about the future a lot. Remember when we moved in together and you finally felt comfortable enough to fart in front of me? I knew you were special before that, but that was a defining moment for us!”

Yes, still cheesy! But you get the point.

The Punchline: Mention the “M word”

Now, like all of the other decisions you have to make when planning your proposal, you’ll have to decide what to actually say when “asking” your partner to marry you. It could be an actual question, or not. Just make sure that some variant or synonym to “marry” is in there. Here are some ideas:

  1. The standard “Will you marry me?” is a tried and true classic. Short and to the point.
  2. A more modern “I’d love it if you’d be my wife/husband/partner” gets the point across.
  3. Using singing, a billboard, or a jumbotron are all options, too. Remember The Wedding Singer?

Just don’t approach it like this guy and you should be fine:

This is arguably the most important part of your marriage proposal script, so please write this part down!

5. Determine How to Photograph Your Proposal

A man proposes to his partner in a Connecticut park.

Look, you’re doing all this work in planning your proposal. Why wouldn’t you capture it so that this memory can be remembered visually, too? Wedding photographers offer proposal photography as a service, too. Often times, it’s the first step in building a great relationship that can last up to your wedding day and beyond. Consider hiring one for this awesome moment!

Find a proposal photographer

If you’re looking for a proposal photographer, I can help with that. This post explains how to find the perfect wedding photographer; many of us also offer proposal services.


Do you prefer a DIY approach? Then be sure to check out my post on how to photograph your own proposal.

Account for photography in your proposal script

If you will be having your proposal photographed (or photographing your proposal yourself), be sure to work this into your script in step 4. This is pretty easy in concept; here are two examples:

  • Hired proposal photographer: If you’re hiring a photographer to capture your proposal for you, they should be helping you plan as much as you’d like them to. The one thing they should take the lead on, however, is communication. Your photographer will need to know approximately where you’ll be when you plan to propose (so they can decide where to watch from) and what your proposal queue will be (so they can will know when thing’s about going down). 
  • DIY proposal photography: “I was hoping we could take a really good selfie, one where neither of us is holding the camera this time.”

6. Practice Your Proposal

Look, this will be one of the biggest performances of your life. Before you get up there on that figurative stage, you must consider rehearsal part of how to propose. There’s no shame in getting down on one knee in private and/or reciting your proposal script in front of a mirror.

7. Drink Some Water and Breathe

I’ll keep this part simple: passing out in front of your partner should not be a part of your proposal plan. To that end, remember to hydrate beforehand and breathe! Here are some more tips from one of my past proposal photography clients:

  1. Incorporate your significant other’s personality, passions, and likes into your proposal.
  2. Tell your partner just enough to get them where they need to be, when they need to be there.
  3. Communicate with all of your co-conspirators directly.

8. Bonus Tip: Be Quiet About Planning to Propose

Maybe this goes without saying, but you probably shouldn’t tell too many people about your plan to propose. Undoubtedly, if you’re hiring a proposal photographer, then tell them. Or if your How involves other people being there and they have to be in on the plan, go for it. But it’s probably not a great idea to tell people just to tell people. It is a surprise proposal, after all.

Now You’re Ready to Propose

You’re ready, you’re brave, and now it’s time to propose. Your partner’s going to love it! But don’t stop reading here, read on for some advice on where to propose in Connecticut.

Where to Propose in Connecticut: Best Location Ideas

Connecticut…we have a beautiful state. I’ve taken the time to explain elsewhere why it’s perfect for weddings, so why wouldn’t I feel the same about proposing? Naturally, then, here’s my list of the best places to propose in Connecticut.

Proposing in Greater Hartford

Pratt Street, Downtown Hartford

Currently closed to vehicular traffic and lined with businesses, Pratt Street is the perfect place to go for a stroll and start your Connecticut engagement. (It’s also the home to a really cool wedding venue, The Society Room of Hartford.)


The quintessential farm town, Ellington also has plenty of parks, businesses, and attractions with hills providing great views. This makes it a strong candidate for a fall Connecticut proposal. For example, you could go apple picking at Johnny Appleseed’s Farm and pop the question there.

Trinity College, Hartford

South of downtown and with a beautiful, sprawling campus, Trinity College’s architecture makes it a really nice place to propose in Connecticut.

Hubbard Park, Meriden

Complete with its own outdoor amphitheater and plenty of trees, Hubbard Park would make for an awesome fall, spring, or summer proposal.

Talcott Mountain State Park, Simbury

When considering where to propose in Connecticut, the base of Hublein Tower in Simsbury is an excellent option.

For the hikers and woods-lovers, Talcott Mountain State Park is a really good hike as well as a perfect Connecticut proposal location. This place is also home to one of the best elevated views I’ve ever visited in our state, where Heublein Tower is perched.

Blue Back Square, West Hartford

Engaged couple during West Hartford Blue Back Square marriage proposal and engagement photo session

With small city downtown vibes, Blue Back Square provides awesome year-round beauty for your Connecticut engagement. There are a ton of things to do in this area and the diversity makes it a great place for proposal photos.

One of the times that I photographed a proposal in West Hartford, it was freezing cold. The couple had such a great time that it didn’t matter that they couldn’t feel their fingers!

Wickham Park, West Hartford

You have to pay a small fee to get into Wickham Park (about $10), making it a little more “exclusive” than most other parks in the state. And let me tell you, it’s worth it. Rivaling Harkness Memorial State Park in terms of beauty, Wickham is definitely on par with aesthetic diversity, with everything from water features to an elevated view of the downtown Hartford skyline. It’s also a wedding venue.

Proposing in the Mystic Area

Avery Point, Groton

Home to one of UConn’s campuses as well as famed wedding venue Branford House, Avery Point is one of the state’s most beautiful pieces of public land. This place is perfect for a picnic and walk, with plenty of water views and three lighthouses on view. An ideal Connecticut engagement location for sure.

Downtown Mystic, Mystic

One of Connecticut’s more popular spring and summer destinations (and really loved by New Yorkers, for some reason), downtown Mystic has it all if you’re planning to propose. You’ve probably visited here before, maybe making it a candidate when you plan your proposal. And the plethora of businesses, from restaurants to jewelers, helps check many engagement boxes.

Mystic River Park, Mystic

Home to the famed bascule bridge, Mystic River Park is the small pier/boardwalk that’s next to little green. Yes, it’s right there by downtown Mystic. Not many people know its name though, so it deserves its own entry in this list of places to propose in Connecticut!

Saltwater Farm Vineyard, Stonington

If you and your partner are wine lovers, give Saltwater Farm Vineyard a look when considering where to propose in Connecticut. This place is beautiful, spacious, and has great wine.

Stone Acres Farm, Stonington

A really nice wedding venue and home to an active farm stand, Stone Acres Farm actually has very strong ties to the Mystic restaurant scene. Therefore, its management hosts intimate, multicourse meals a few times a year that are announced only a little while before they take place. If you two are foodies, this could make for a great Connecticut proposal location idea.

Stonington Point, Stonington

If the shoreline and water views are your thing, Stonington Point should be near the top of your list when considering where to propose in Connecticut. This part of the Borough, as locals call it, is essentially a long, one-way strip lined with restaurants and shops. At the end is the Point, which has a parking lot, small beach, and small park with a lighthouse museum. Picturesque!

Harkness Memorial State Park, Waterford

It seems like that nobody’s ever heard of Waterford, yet everyone knows Harkness. Harkness is OK (yes, I’m being sarcastic). I’ve photographed several Connecticut engagement sessions here and it’s always a hit location.

Proposing in the New Haven Area

East Rock, New Haven

Ever been to the top of the world in Connecticut? For epic views in the southwest part of the state, the top of New Haven’s East Rock makes for a great place for proposal pictures.

Lighthouse Point Park, New Haven

When considering where to propose in Connecticut, Lighthouse Point Park in New Haven is a great option.

If you hadn’t noticed, I love lighthouses. So if you’re planning to propose in the New Haven area, Lighthouse Point Park comes to my mind first. At 82 acres, this place provides a ton of room for a private proposal.

Yale University, New Haven

When focusing on the New Haven area, a list of places to propose in Connecticut wouldn’t be complete without including Yale. It’s big, city-situated campus is loaded with old architecture. Taking a guided tour and then breaking off on your own might make for a good proposal plan.

Wooster Square Park, New Haven

Located in the Wooster Square area of the city, this small park is great for just chilling on a nice morning or afternoon. There’s plenty of on-street parking and restaurants nearby, making it a great Where for your proposal plan!

Closing Remarks: You’ve Got This

Hopefully this guide on how to propose is useful to you! When you get down to it, I truly believe that planning a proposal is this simple. The hard parts, of course, are dealing with the nerves and actually going through with it. Again, I highly recommend hiring a proposal photographer to help you plan and capture your engagement.

Before you go, please feel free to check out my other wedding planning resources. You may want to bookmark them for after your partner says “yes”!


I used the following references at different points in this post:

  1. “What Guys Really Think About When They’re Going to Propose Marriage,” Cosmo Frank, Cosmopolitan
  2. “How Do You Know When You’re Ready to Propose? We Asked a Real Couple,” Alaina Leary Lavoie, Equally Wed
  3. “The History of the Diamond as an Engagement Ring,” American Gem Society
  4. “15 Romantic Ways to Propose Without A Ring,” Jennifer Skulski, Wedding Hashers
  5. “Blood Diamonds,” Aryn Baker, Time Magazine
  6. “As New Yorkers Flee, Once-Humble Seaside Town Sees Bidding Wars,” Britton O’Daly, Bloomberg
  7. “Lighthouse Point Park,” Wikipedia

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