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5 Holiday Season Proposal Tips

A beautiful handmade Christmas tree ornament that asks if she'll marry you.

Photo courtesy of Little Wee Etsy Shop

Thinking about popping the question this holiday season? You’re not alone. According to national statistics, about 1/3 of couples get engaged around the holidays. If you’re planning your proposal now, here are a few tips for nailing it.

1. Plan ahead. While it may seem right to spontaneously ask her to marry you while you’re binge-watching “Homeland” together, she’ll appreciate it even more if she can tell you put some serious thought into your proposal ahead of time. Also make sure to sketch out a schedule of events beforehand to ensure that everything comes together as planned. She’ll be telling your engagement story over and over again, so make sure it’s a good one.

2. Make it about both of you. Love flying? You might think about popping the question during a helicopter ride. But is it her thing, too? If she’d just be going along for the ride, consider something that’s important to both of you instead. For example, if you both love wine tasting or cycling, think about ways to incorporate shared interests into your proposal.

3. Use the season for inspiration. If you’re not quite sure how or where to pop the question, use the season for cues. For example, if you both love hitting the ice skating rink, a favorite sledding hill or local holiday light display together, consider using one of these locations for your proposal. Incorporating nostalgia is another good option. Choosing the joint where the two of you shared your first cup of hot cocoa together could be the perfect, memorable proposal spot.

4. Add some bling. Including a ring in your proposal makes it official. Whether you propose with a diamond, sapphire, topaz, pearl, a simple band or even a placeholder ring until you can go ring shopping together — whatever makes most sense for her — she’ll know you mean business.

5. Include her loved ones. Really knock your proposal out of the park by incorporating her closest friends and family into this special moment. Consider enlisting a sibling to secretly lure her to the proposal location or size up her dream ring beforehand, or arrange to have her nearest and dearest meet you at a nearby bar for a celebratory drink afterward.

How do you plan to pop the question this winter?


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One Response to “5 Holiday Season Proposal Tips”

  1. James Says:

    Great advice!

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