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Category Archives: 2019 August

What to Say When Proposing: Ultimate Guide to Popping the Question



What to Say When Proposing


“Will you marry me?”


That’s the easy part.


If you’re wondering what to say when proposing, you’re in good company. Abruptly asking the big question isn’t ideal for every couple. We want to justify the question and create a heartfelt moment.

But the pressure – even when we’re sure this is the right step – can leave us tongue-tied. This is not the time to be at a loss for words or to falter when talking about how we feel.

These worries are normal. There’s a lot we can do to ensure this event is as special as you both dreamed. Here’s your complete guide to figuring out what to say when proposing.


1. Do NOT stick to a script – what to say when proposing


It’s good to sit and write down everything you’d like to say. However, you’re not going to memorize and recite it, let alone whip out the sheet of paper and read it to them. We want to be genuine. We want our partners to recognize that this is an authentic expression of how we feel.

If you’re not usually very romantic or emotionally expressive, that’s okay. Just take all of the advice here into account, and remember that you don’t have to pretend to be a different person to get the message across.


2. Have a degree of certainty


Right behind worries of what to say when proposing is, “What if they say no?” We’re not fortune tellers, so you’re going to have to take a chance here. That said, you should definitely have an idea of how your partner feels about the future of your relationship.

Ask yourself the following:

  • Have we discussed marriage before?
  • How did they respond to discussions of marriage?
  • Has anything changed since we last discussed marriage?
  • When we talk about the future or make future plans, do we include one another?

Your answers to these questions don’t have to be completely perfect, but they’ll reveal whether or not now is the right time to propose.


3. Respect their preferences


Let’s say you’re looking forward to a rather grandiose proposal. Would this embarrass your partner? Would they feel compelled to agree to the proposal just because there are people watching? If they are a private or shy person, avoid putting them on the spot.

Determining the setting can be as important as what to say when you propose. For instance, if they’re outdoorsy, proposing on a hike is more memorable and happier than during a romantic dinner.


4. Reflect on your personal growth


Chances are, this relationship has improved your life for the better. If you research what to say when proposing, examples include things like, “You complete me.” Now, that exact phrasing is a cliché, but it gives us the right idea.

Explain to your partner what you’ve gained through being with them. Maybe you became a more compassionate or considerate person. Perhaps you found the ambition to succeed because you wanted to create a better future with them. These are good points to include when you propose.


5. Reflect on your relationship


When you propose, open up with a very brief synopsis of your relationship. Mention how long you’ve been together, or how you felt the first time you met them. A basic example: “When I went to a party at my friend’s house three years ago, I never expected I would meet the love of my life there.”

In the first place, this orients you both. You’ve been on a journey together, a journey which has led to this moment. And if your partner has been anticipating a proposal at some point, their interest in what you say next will be piqued. We want both parties to be fully present and tuned in.


6. Know the deal with the ring


As you know, proposals traditionally come with a ring. This is another area where special considerations are in order.

  • Would my fiancé/e want to pick out their own ring?
  • Should I get a ring in the meantime that could act as a placeholder for the one they want?
  • What style of jewelry does my partner normally wear?
  • If I didn’t propose with a ring, how might they feel about that?
  • Would they appreciate that it seemed so spontaneous that I didn’t have one ready?
  • Have they ever dropped hints about what kind of ring they would like?
  • What is their ring size?

Ultimately, the ring is not the main feature, but it is an important prop. The final dream ring can be sorted later, but you need to be clear on how a ring will factor into your proposal.


7. Allow yourself to be nervous


Hey, proposing is a big deal. If your hands shake or your voice wavers, that’s understandable. It won’t ruin the moment. Let yourself feel a little overwhelmed if that’s how it really is.

Nervousness will never matter if you maintain good eye contact and continue saying what you want. No matter how shaky you become, remain focused on your partner. After all, it will be over in a few minutes, and if all goes according to plan, you’ll be celebrating.


8. Determine how much of a surprise it should be 


It’s simple: some people like surprises, and others don’t. If your partner is anticipating this but would love telling others about their stunning surprise proposal, plan it at least a few weeks after their last mention of getting engaged.

If your partner does not like surprises, let them know this date is special from the get-go. Don’t admit outright that you’re proposing, but let the occasion speak for itself. Use your intuition and experience with them to create a situation they would appreciate.


9. Tell them why


“When you know, you know” does not suit every couple. Many of us know exactly what it is that makes someone the perfect partner. What better time to share that than during your marriage proposal?

It’s a good rule of thumb if you find yourself at a loss as to what to say during proposal time. Maybe it’s their kindness, loyalty, sense of humor, or all of the above. As long as it’s the truth, they will love to hear it.


10. Don’t replicate someone else’s experience


Ultimately, the perfect proposal will look a little different for every couple. It might seem easier to go with what worked for someone else, but this can ring hollow for you and your partner.

Personal touches are welcome here. Bring them their favorite flowers, play your favorite song, or start off by sharing an inside joke. Take them to the place where you had your first date if you want something more sentimental.


Final Thoughts on What to Say When Proposing


In the end, it helps to ask one question – are you overthinking the proposal? If so, stick to these key points:

  • Authenticity rules

    Don’t rattle off a speech you’ve memorized, and don’t merely repeat what you’ve heard elsewhere. Your partner knows you and can tell when you’re being genuine. If that includes you being a little nervous, it’s fine.

  • Be considerate

    Don’t surprise or embarrass your partner. Take their personality into account and plan the event accordingly. This is probably not the occasion to ask them to step outside of their box.

  • Tell a story

    If you’re worried about what to say when proposing, simply refer back to your relationship. If you had a funny first meeting, or have overcome some serious challenges, these are great points to hit on leading up to the question.

Just in case you’re really feeling the pressure, consider this last tip:

You don’t have to ask at all!

Sometimes, staying mum works in your favor. Have them go on a treasure hunt that ends in a written message popping the question, or spell it out with candles or flower petals. Hire live musicians to play your song as you drop a knee. It’s your chance to show someone how important they are in your life, and we can’t always put that into words.


Other Helpful Wedding Proposal Pages

  1. 5 Best Places to Propose in Boston
  2. She said YES! A proposal at Public Garden
  3. Fan Pier Park Wedding Proposal
  4. Boston Public Garden Proposal


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5 Best Places to Propose in Boston



Dreaming of a picture-perfect proposal? Most of us do, but like a lot of major life events, it’s all in the planning. If you don’t want to spontaneously pop the question at a less-than-perfect moment, there are plenty of locations all around the city that are sure to stand out in your mind and memories forever. We proudly present five of the best places to propose in Boston.


1. Fan Pier Park


What’s your point of view? Some of us believe we’ll have our whole lives to enjoy intimacy. For the proposal, focus on wow factor. That’s easy to arrange with the breathtaking waterfront views available at Fan Pier.


To make a day of it, start out at Rowe’s Wharf, where you and your soon-to-be betrothed can hop on a few bikes and make the most of the Boston Harborwalk. It’s a scenic ride to Fan Pier, with museums and fascinating architecture to enjoy along the way.


Once you’ve arrived, hit up Babbo Pizzeria e Enoteca on Fan Pier Boulevard for some of the most popular wood-fired pizza Boston has to offer. Cap it off with some of their famous gelato, and head back out just in time for the sun to go down and the city lights to come up.


Alternatively, start your evening out at Committee, one of the city’s hottest spots serving Mediterranean fare. Have a few of their clever cocktails on the patio before making your way closer to the water’s edge. There, a stroll along the cobblestone path sets the tone leading up to the big moment.


No matter how you spend your time before the big question, Fan Pier provides some of the best nighttime views of Downtown. Better yet, it’s one of the best spots in all of Boston to take photographs. This makes it an ideal proposal spot for those who want a stunning, momentous snap of the occasion.


2. Christopher Columbus Park


Like Fan Pier, Christopher Columbus Park features plenty of waterfront views. Still, there is perhaps more versatility in proposal planning when you include the park, especially depending on the season.


For instance, a spring or early summer proposal begs for a setting in full bloom. Pack a picnic lunch, or grab some carry out from one of the many delicious nearby eateries. Walk it off with a pleasant, easygoing wander through the Rose Kennedy Rose Garden. There are many varieties of gorgeous and fragrant perennials to behold.


From there, make your way out to the fountain in the middle of the park, where you can pop the question amongst the park’s many shade-providing trees.


If a more celebratory social gathering is in order, consider a fall or winter proposal in the park. Late November brings the Annual Trellis Lighting Ceremony, where soft blue lights drape the trellis and the hot chocolate flows. This location is well known as one of the most romantic places in the city, in addition to being one of the five best places to propose in Boston. Don’t be surprised if someone nearby drops a knee as well.


For lovers who want a fresh start, consider the heralding in the new year with a crisp, brilliantly lit proposal. Christopher Columbus Park is an excellent place to catch the Harbor’s New Year’s fireworks display.


3. Boston Public Garden


For a park-like setting with a little more fanfare, try Boston Public Garden. It’s a great place to end up after visiting one of the nearby cafes or restaurants. Prize-winning flowers and famous sculptures adorn the 24-acre botanical space.


Make your move as you gaze down at the lagoon from the historic trellis bridge or traverse the lagoon itself in a swan boat. Either way, your ears might be privy to some mood music courtesy of one of the Garden’s many visiting performers, known as buskers.


If temps are low, start out with some ice skating at nearby Boston Common. Grab a hot drink and stroll through the Garden to peacefully admire the city lights. It’s significantly less crowded during the colder months.


If all goes according to plan, there’s good news. In addition to being one of the best places to propose in Boston, the Public Garden hosts weddings. Imagine yourself saying “I do!” beneath the tendrils of great weeping willow trees, with one of those infamous swan boats floating by in the background.


4. Acorn Street, Beacon Hill


We could describe Acorn Street as charming, old-fashioned, and romantic. Yet it also has a reputation for being one of the most photographed locations in the city. If you’re looking for an intimate moment, is a photo mecca really one of the best places to propose in Boston? As it turns out, perhaps.


Cobblestones characteristic of old Boston pave the private little street, which is narrow and lined by row houses. It extends for a mere block between West Cedar and Willow. The real headline here is that this historic little picturesque gem is located in Beacon Hill. Therefore, there are a wealth of date options to explore before finding yourself on this storied pathway.


History and architecture buffs will enjoy Beacon Hill’s famous walking tour, which takes visitors through many historical areas, including Louisburg Square. Outdoorsy types can start the date at Charles Hill Esplanade for some kayaking, where they might afterward happen upon a pop-up brewery.


Charles Street is also a great boutique shopping destination, where you can buy a few nice things for your honey before presenting the ring. The restaurants are well-represented as well. Go elegant Italian at Toscano, or try a romantic French bistro like The Hungry I. The latter is a mere 0.1 miles from your proposal destination, Acorn Street.


Imagine Acorn Street in the fall just before sunset, with fallen foliage and shades of ochre and rust. Pop the question in the autumnal glow on this quiet street; you won’t need a photograph to remember it forever, but you should take one anyway.


5. Comm Ave (Commonwealth Avenue)


If you’re unsure as to which avenue to go with your proposal, just go Commonwealth Avenue. Historical areas, gardens, malls, and more make it a prime destination for couples who want to experience Boston and hit a major milestone along the way.


For starters, book a room at Comm Ave’s No. 284 – A Boston Guest House. An extraordinary take on a hotel, it offers luxurious rooms ensconced in a brick building in the Back Bay neighborhood. Their list of services and amenities is rich and varied, offering guests everything from photographic services and chauffeured limousines, to dentist appointments and theater tickets. It is a singularly excellent place from which to start a weekend getaway.


No. 284 is close to Copley Square, where you can visit the Boston Public Library and a whole host of architectural landmarks. The hotel is also a few skips away from a lot of fine dining, from Deuxave, serving Modern French, to Casa Romero, rated the best Mexican restaurant in New England.


The Back Bay neighborhood also features so many shops and cafes that there truly is something for everyone. Finally, it’s not far from Fenway Park, should you be sports fanatics looking to catch a game.


All told, Comm Ave is a great jump off point for a Choose Your Own Adventure-style proposal. With the best of the city within arm’s reach, it is inarguably one of the best places to propose in Boston.


In Conclusion – Best Places to Propose in Boston


Ready to lock it down in Beantown? The rundown on five spots today should have you on the right path. To summarize:


  • Fan Pier – The picture-perfect moment you’re looking for. Even if you’ve lived in the Boston area all your life, capturing a proposal in front of the iconic city skyline is something many couples dream of.


  • Christopher Columbus Park – A rosy picnic proposal near the fountain, or a wintertime celebration under trellis lights or fireworks? Either way, there are chances for a very one-on-one encounter that isn’t devoid of that extra something special.


  • Boston Public Garden A proposal spot and a wedding venue all in one. Take your future spouse on a famous swan boat, or on a stroll through stunning botanicals after having a day to remember at one of many surrounding attractions.


  • Acorn Street – A proposal straight out of the movies. Amble down this historic cobblestone street, basking in the glow of your love. This neighborhood is the perfect place to make what they think is the average coffee date a night to remember forever.


  • Commonwealth Avenue – A luxury stay in a prime location will springboard you into a whirlwind of activity – museums, restaurants, shopping, sporting events. Or just order room service and take a stroll through a historic neighborhood. A great option for those who want to have a long weekend together.


Finding the right spot can take a lot of pressure off of a proposal. Hopefully, your jitters have melted away with the realization that all will go well when you choose one of the best places to propose in Boston.


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