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Holiday Proposal Checklist

Holiday Proposal Checklist

Holiday Proposal Checklist:

Everything You Need To Nail It.


The family’s all in town. Everything is lit up and glowing. A sparkling fresh year is just around the bend. Could there be a more romantic time to propose? Christmas and New Year’s consistently top the charts for the most questions popped. Makes sense, since it’s one of the happiest times of the year for most people. 


If you’re planning to propose during the holiday season, there are a few special things you should know and of course, a bunch of to-dos to check off. Make the planning process easier and as fun as possible by tackling this checklist!

The family’s all in town. Everything is lit up and glowing. A sparkling fresh year is just around the bend. Could there be a more romantic time to propose? Christmas and New Year’s consistently top the charts for the most questions popped. Makes sense, since it’s one of the happiest times of the year for most people. 


If you’re planning to propose during the holiday season, there are a few special things you should know and of course, a bunch of to-dos to check off. Make the planning process easier and as fun as possible by tackling this checklist!


Get To Know Your Partner's Style

Start snooping around their jewelry box, or if you’re open about engagement plans, directly ask what they prefer. If it’s a surprise, sneak a ring you know fits well and size it up with our free, printable ring sizer to make ordering a cinch. 

Tip: Moms, sisters, and BFFs are also excellent sources of ring insights. Don’t be afraid to ask them for help!

Start snooping around their jewelry box, or if you’re open about engagement plans, directly ask what they prefer. If it’s a surprise, sneak a ring you know fits well and size it up with our free, printable ring sizer to make ordering a cinch.

Tip: Moms, sisters, and BFFs are also excellent sources of ring insights. Don’t be afraid to ask them for help!

Questions To Ask:

DO THEY LIKE MODERN OR TRADITIONAL?

WHAT SHAPE DO THEY PREFER?

DO THEY LIKE MODERN OR TRADITIONAL?

WHAT SHAPE DO THEY PREFER?

Would they like something that's one of a kind?

Seeking A Parental Blessing?

Do that asap. If you’re doing it the old fashioned way, pencil in time with your partner’s parents. They’ll appreciate the gesture, even if it’s more of a heads up vs. traditional “permission.”

Seeking A Parental Blessing?

Do that asap. If you’re doing it the old fashioned way, pencil in time with your partner’s parents. They’ll appreciate the gesture, even if it’s more of a heads up vs. traditional “permission.”

Make A Plan.

Where do you plan to propose: under the tree at home or at a swanky restaurant decked out in holiday vibes? Make sure you decide, and then make any reservations well in advance. Restaurants get booked up early for holiday parties and New Year’s is awash with revelers, so make sure your plans are buttoned up asap. Consider there might be special hours or set menus, too. 

Tip: The holidays are always crazy, proposal or not. Back up your Plan A with a solid Plan B just in case things go awry at the last minute.

Make A Plan.

Where do you plan to propose: under the tree at home or at a swanky restaurant decked out in holiday vibes? Make sure you decide, and then make any reservations well in advance. Restaurants get booked up early for holiday parties and New Year’s is awash with revelers, so make sure your plans are buttoned up asap. Consider there might be special hours or set menus, too. 

Tip: The holidays are always crazy, proposal or not. Back up your Plan A with a solid Plan B just in case things go awry at the last minute.


Find The Ring

There’s a lot to explore, but if you’ve done your homework on your partner’s personal style, you’ll have a good head start. You’ll need to figure out a budget, too (and we have flexible payment and financing options that can help with affordability). Don’t forget to find a safe place to hide the ring if the proposal will be a surprise.

There’s a lot to explore, but if you’ve done your homework on your partner’s personal style, you’ll have a good head start. You’ll need to figure out a budget, too (and we have flexible payment and financing options that can help with affordability). Don’t forget to find a safe place to hide the ring if the proposal will be a surprise.

Tip: If you’re custom-designing a ring, make sure to design and place your order in advance. We typically recommend a minimum of four to eight weeks. With the holidays, it’s not a bad idea to order even earlier. You can also set up a Lifetime Care Plan to keep the ring safe in case of a lost stone, broken prong, or anything else that might pop up.

Tip: If you’re custom-designing a ring, make sure to design and place your order in advance. We typically recommend a minimum of four to eight weeks. With the holidays, it’s not a bad idea to order even earlier. You can also set up a Lifetime Care Plan to keep the ring safe in case of a lost stone, broken prong, or anything else that might pop up.

Button Up That Set Up

Booking a photographer? Planning to decorate a special proposal spot? Enlisting the help of others? Make a list of everything you’ll need and then add it all to cart and stow away for the special day. 

Tip: If anyone’s helping you set up on the actual proposal day, write down instructions they can refer to ahead of time so it unfolds seamlessly.

Button Up That Set Up

Booking a photographer? Planning to decorate a special proposal spot? Enlisting the help of others? Make a list of everything you’ll need and then add it all to cart and stow away for the special day. 

Tip: If anyone’s helping you set up on the actual proposal day, write down instructions they can refer to ahead of time so it unfolds seamlessly.

Prepare Your Speech

You’re probably pretty confident it’ll be a yes—but you still want to elaborate on the reasons you love your partner and why you can’t wait to spend your life with them. A proposal speech doesn’t have to be long or poetic. Just make it heartfelt and it’ll automatically be memorable.

Tip: Don’t forget to practice it so it flows when you’re in the moment and having all the feels.

Prepare Your Speech

You’re probably pretty confident it’ll be a yes—but you still want to elaborate on the reasons you love your partner and why you can’t wait to spend your life with them. A proposal speech doesn’t have to be long or poetic. Just make it heartfelt and it’ll automatically be memorable.

Tip: Don’t forget to practice it so it flows when you’re in the moment and having all the feels.

Plan Something Special For Post-Proposal

Yay, you’re engaged! Congrats…now let’s celebrate! Show your partner you put extra thought in. Have a photographer or videographer film the whole thing. Have a bottle of wine ready to toast the moment. Have the restaurant bring out an extravagant dessert. Steal away for an overnight you pre-booked somewhere meaningful to you both. You’ll get serious bonus points and kick off your engagement in bliss.

Plan Something Special For Post-Proposal

Yay, you’re engaged! Congrats…now let’s celebrate! Show your partner you put extra thought in. Have a photographer or videographer film the whole thing. Have a bottle of wine ready to toast the moment. Have the restaurant bring out an extravagant dessert. Steal away for an overnight you pre-booked somewhere meaningful to you both. You’ll get serious bonus points and kick off your engagement in bliss.