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Truly Blog » Gift Occasions » Weddings » Wedding Proposals & Engagements » How To Have a Stress Free Proposal

How To Have a Stress Free Proposal

After years of searching for the love of your life, you’ve finally found the one. She’s got it all: personality, looks, and your family and friends adore her. You do your homework and find the perfect engagement ring to show your commitment.

The hardest part is over, right? Wrong. Although choosing the ring is a huge step, the proposal is where you have to shine. With proper planning, you can create an experience for your future bride-to-be that will never be forgotten. This could be a very stressful process, but don’t panic!

Here’s the definitive checklist for ensuring a stress free, special proposal:

Jump To a Section Below

  • 1. Historical Connections
  • 2. Location
  • 3. Photography and Videography
  • 4. Friends/Family Inclusion
  • 5. Evening Accommodations
  • 6. Timing
  • 7. The “Ask”
  • 8. Engagement Gifts
  • It’s Time to Pop the Question!

1. Historical Connections

If you’re at a point in your relationship where you feel it’s time to propose, you have a history with your significant other. Tap into any past experiences and intertwine them into your proposal. Think about inside jokes, momentos, quotes, or even specific locations that have strong meaning to the both of you.

Pro Tip: Think about what’s most meaningful to your partner. What will make her laugh? What can show her you listen? Where will she be most comfortable saying, “yes!”? Consider these factors and tie them into the proposal.

2. Location

Location is potentially the most important factor when planning your proposal. Where you choose to ask her will dictate all of the other components to the event. Those components will be outlined further in this post. Select a location that allows you to provide a scenic backdrop (whether it’s indoors or outside), capture the moment on camera and video, potentially include friends and family, and plan for the evening accommodations for you and your fiancée.

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Pro Tip: If an outdoor proposal is on your radar, have a backup plan! Weather could alter the timing and ruin any potential opportunity for photography or videography. Try to select a location that has an indoor option if the weather isn’t cooperating.

wedding proposal ideas
Propose under this beautiful arch near Glenapp Castle

3. Photography and Videography

The last thing you want to worry about when proposing is finding someone to capture the moment. Plan ahead by finding a professional that specializes in proposals. With technology continuing to improve, there’s no excuse to not have the proposal on video, or at least high-quality pictures.

Pro Tip: Communication between you and the person capturing the moment is a must. Throughout the planning process there may be changes to what you had in mind initially. As long as you and the photographer/videographer are on the same page, you’ll be set!

Learn Photography
Or: give a loved one a photography class, so they can record your proposal

4. Friends/Family Inclusion

Pending a destination proposal, you may want to include family and friends. This is dependent on whether you think she would prefer a more private and intimate setting, or create a group environment for all to enjoy. Whatever you decide is best, be sure to keep everyone updated on the itinerary so that everyone is on the same page.

Pro Tip: Look at past events that have had meaning to you both. Has the inclusion of family and friends strengthened the impact of past moments? Your history might give you the answer to this question.

5. Evening Accommodations

The proposal doesn’t stop once she says, “I do.” To cap off the momentous occasion, be sure to plan appropriately for the evening accommodations. Although it’s not necessary to spend the evening away from home, it will add to the allure of the event.

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Pro Tip: Make the entire event something to remember. Continue the blissful feeling and carry it to a romantic evening of celebration.

6. Timing

There are two pieces to the timing puzzle that must fit appropriately. This includes the time of year or season and time of day in which you plan on proposing. According to Chillisauce, 33% of men believe Christmas Eve is the best time of year to propose while 23% of women would prefer Valentine’s Day. Time of day in which you propose will be heavily dictated by all other factors involved in the event.

Pro Tip: Many of the factors listed above will contribute to the timing of the proposal. Consider the historical connection of the timing of the event (anniversary, etc.), most scenic time of day for pictures, availability of family and friends to be included, and available evening accommodations.

7. The “Ask”

There’s no need to have a long and drawn out proposal. Over half of women actually prefer their partner cuts to the chase and just say the magic words, “will you marry me?” Prepare your speech and have it memorized. You want to be able to hold your partners hand throughout the process and not fumble around with notes. Worst case scenario is your ask is too extended and she becomes uncomfortable during the process. Just ask, she’ll appreciate it!

Pro Tip: It’s only natural to be nervous when dropping down on one knee. Practice. Practice. Practice. Delivery is key, and the more you practice, the more natural your delivery will be.

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8. Engagement Gifts

Not only is the proposal a stressful process for you, your partner will be overcome with emotion. Naturally, she’ll be exhausted from the event and hopefully overcome with joy. Treat her to an engagement gift she’ll never forget. There are a number of options that will give her the opportunity to unwind with a spa day, or even dine on the finest cuisine. Think of this as the last step before diving into wedding planning. It’s always best to start refreshed!

Pro Tip: Between the engagement ring and planning the proposal, it’s difficult to fathom spending more on an additional gift. Look into alternative financing with a credit card that offers 0% intro APR. This will allow you to pay off the expenses over time versus paying all the expenses in one lump sum or accumulating interest.

Engagement gifts
Something delicious as an engagement gift idea

It’s Time to Pop the Question!

Regardless of the amount of preparation, there will be things that are out of your control throughout the proposal process. Maybe there’s a severe weather warning or your partner becomes ill before the festivities take place. Don’t worry about the things you can’t control!

Instead, focus on what you can control. Prepare accordingly and use this checklist as a guide. Expect to adapt and make it the most memorable experience you can!

Rae Oliver
Rae Oliver

I am an experienced writer specializing in travel, food, weddings, and well-being. Continuing my nomadic lifestyle I am currently based on the beautiful island of Malta.

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