Planning the Perfect Holiday Engagement

by Sasha t on Sep 19, 2023

Planning the Perfect Holiday Engagement - Jack Weir & Sons

So you’re ready to pop the question - ready to commit to a life of love with the person who still makes your heart skip a beat. Congratulations! And what better time to do it than over the holidays? It’s a time steeped in sentiment and romance, magic and joy - an ideal time to celebrate such a beautiful personal milestone. 

The holidays are beautiful and full of magic but are also usually jam-packed with exciting events, plans with family, and last-minute must-dos. So, planning the perfect holiday engagement requires not only personal sentiment and  surprise but meticulous preparation and attention to detail. 

October is the perfect time to start planning this momentous occasion - and we want to help ensure you are as prepared as possible to create this magic moment. So let’s start with the basics. 

3 big diamond rings

The Big Decisions 

  • Know Your Partner's Preferences: Before anything else, ensure you understand your partner's taste. Would they appreciate a private moment or a grand gesture in front of family and friends? Keep their comfort and preferences at the forefront.
  • Pick the Right Holiday: The December Holidays can be a busy time - so think about your other commitments over the season and how they might impact your energy and time. Make sure you are leaving plenty of space for excitement and celebration after the proposal itself.  Think about holidays or days around the holidays that may have personal significance for the two of you. 

Target rings

(Emerald target ring, Sapphire target ring, Sapphire target ring

  • Choose the Ring Thoughtfully: If you're going the traditional route, invest time in selecting the perfect engagement ring. Consider if your partner would like to choose it together. If you're unsure about the style, ask your friends or family, or opt for a placeholder ring and choose the permanent one together later. We can certainly help you with this choice - with a wide range of options here at Jack Weir & Sons, we have something for every taste and budget. 
Chunky gold pieces

Plan the Logistics:

  • Pick a memorable date, time and location -  If you're not proposing at home, choose a location that holds sentimental value. It could be where you had your first date, a favorite vacation spot, or a beautiful holiday setting like in front of a massive Christmas tree or during a fireworks show. Consider if you want to propose at the beginning, middle, or end of the holiday celebrations. And don’t forget to think about the weather and have a plan B if you’re thinking about proposing outside! 
    •  Private vs. Public: If proposing in a public place, consider the best time to avoid big crowds, unless a crowd is part of your plan! Think about what your partner will most appreciate - an intimate setting with just the two of you. Or a big crowd? Think about what you’ll want to do before and after the proposal and plan accordingly. 
    • Capturing the Moment - Is capturing this moment important to you or your future fiancee? Think about how to engage with a photographer or videographer to capture this moment in a way that feels comfortable to you. 
    Art Deco Pear cut and old european cut rings

    Meditate on the moment

    • Prepare What You'll Say: Think about what you want to convey. Most important is to speak from the heart - you could recall special moments, reasons you love them, your dreams for the future, or your anything else you want to express in this very special moment. 
    • Involve Family and Friends: If your partner is family-oriented, consider involving close family and friends in the proposal. Perhaps they can be part of a surprise or help set the scene.
    • Celebrate Afterward: Plan a post-proposal celebration. This could be a romantic dinner, a gathering with family and friends, or even a weekend getaway - whatever makes the most sense for you and yours. 
    Baguette, asscher and emerald cut rings

    The big thing to remember is that nothing is ever perfect - things might not go exactly as expected, especially during the busy holiday season. Enjoy the chaos, it’s all a part of life.  Even if everything doesn’t go perfectly according to plan, remember the purpose of the proposal. The authenticity of your feelings is the most important part.

    After the proposal, take the time to enjoy the moment and celebrate the new chapter in your relationship. We’re so excited for you and your future together! 

    We’d love to help you pick our your ring and plan your proposal - please reach out to us whenever you’re ready to start talking about your big holiday engagement! 


    At Jack Weir & Sons, we’ve spent the last 40 years traveling to Europe and all over the world, curating extraordinary estate jewels. JWS is where the old world meets the new world. Celebrate life, preserve history, and discover your own priceless heirloom jewel. We are extremely grateful for our clients and the ability to help people to celebrate their special moments through one-of-a-kind jewelry. To share that gratitude and our strong family values, we chose to partner with Baby2Baby. So far, we've donated $125,000. A portion of every sale goes towards children living in poverty to provide them with diapers, clothing, and all the basic necessities that every child deserves. 

    We offer in-person and Virtual Appointments and are happy to answer any questions about your favorite jewel. 

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