proposing at Christmas

Planning on Proposing this Holiday Season? Tips For Success & Proposal Ideas

The holidays are a perfect time to propose. With holiday travel, parties, family and work events filling up the calendar, you will need a little planning to make sure that the biggest question you’ll ever ask goes off smoothly.   Here are three tips from our experts to help guys as they get ready to propose.


1. Proposing: Lock down a date.

While this may sound a little formal, you will definitely need to make plans such as buying tickets or making dinner reservations to ensure that she knows to keep the date open (without giving the surprise away). You want her to keep an evening open so your plans can continue without a hitch. For example, tell her you want to take her to the theater, a play, a concert or special party and tell her you have tickets. This time of year, she’ll be expecting festive events and not necessarily a proposal. Perfect timing to pop the question!

2. Proposing: Secret Shopping

Buying an engagement ring during the holidays is a great idea. Not only are there fantastic deals, but often free shipping and new season’s engagement rings. Take a look at your local jewelry stores for ideas (she likely has given you some clues as to what she likes). After hitting the pavement, find the same or similar setting online for bigger savings.

There are ways to keep it a secret, too. Make sure you use a different email account when making a purchase and make sure you log out so she doesn’t see any trace of a shipping confirmation email from a jewelry store. Erase the history and cookies on your computer or shop during your work break at your work computer to take extra precautions.

3. Proposing: Plan the Proposal

Now that you have the ring, the planning can begin! You can make this proposal as simple or complex as you like–but remember to take note of her personality before going too far. Is she the quiet type who doesn’t like a lot of attention? Don’t do a massive public proposal and stick with a romantic dinner, Christmas tree farm proposal (classic) or something a little more private. Is she an extrovert who loves to be in the spotlight? Consider a public place like a Christmas concert or ice skating rink or large venue where she is sure to capture the envy and attention of all around.

Here are 10 proposal ideas from The Knot to help get you started:

Play Santa

Ask a local department store to let you play Santa for a day. Have one of your love’s friends take her shopping and convince her to sit on Santa’s lap. Once she’s in position, give her the ultimate Christmas gift.


Dazzle Him

Commemorate special moments in your relationship by writing or illustrating each event on a Christmas ornament with paint pens. Decorate the tree with all the special moments. On the tree topper — which you should wait to put in place — write, “Will you marry me?”


Make Every Day Count

Make an Advent calendar. Each door she opens should reveal a sentimental memory or a reason you love her (or him). Hide your proposal behind the door for December 25. If you’re Jewish, use this idea for Hanukkah gifts, with each day’s gift building up to the most important gift of all.


Spell It Out

Write out your proposal with roses in the snow or in Christmas lights on your house.


Enlist Help

Attach plastic antlers and a red nose to your (cooperative, selfless) dog. Then put the ring on a ribbon around the dog’s neck and send the mutt to wake your beloved. If you have two dogs, attach a “Marry me” sign to the second and send them in together. She’ll never forget this Christmas morning! (And then include your dog in the wedding!)


Get Crafty

Make two time capsules. Put souvenirs and snapshots from your relationship into the capsule for the year that’s ending. Put only a ring box into the second, signifying a new beginning in all senses of the word.


Count Down

If you’re at a party, work your proposal into the crowd’s big countdown to the new year. Right before everyone starts screaming, “10, 9, 8…” say, “I want to tell you why I love you so much.” After each number the crowd yells, quickly tell your sweetie a reason (you’ll have to rehearse exactly what you want to say). When the new year arrives and everyone is hooting, simply whisper, “Will you marry me?”


Stay Home

Bah, humbug! If you detest parties and Times Square-sized crowds, plan the ultimate at-home cocoon (no Netflix allowed). Whatever you like, do it to the extreme. If you’re foodies, don’t settle for wine and cheese — think caviar and champagne, the best you can afford. Don’t sleep on your bed — instead, decorate your living room to look like a boudoir, or make a cave out of couch cushions. At the stroke of midnight or when the moment is right, ask.


Take the Cake

Invite your nearest and dearest to a party to celebrate Father Time’s birthday — the beginning of a new year (and a new engagement)! Get or make a life-sized cake. Tell your sweetie you’re going to surprise your friends, and tell your friends you’re going to propose — top secret! At the stroke of midnight, jump out of the cake with a big sign around your neck that says, “(Name), will you marry me?”


Say It With Chocolate

Make reservations at an elegant restaurant and arrange for the waitstaff to bring out two covered desserts. Under your lid will be a heart-shaped cake in her favorite flavor; under hers, a ring box nestled in a bed of rose petals. Once revealed, instruct the waiters to bring over a bottle of bubbly.

With all of the moving parts during the holiday season, proposing can be a little tricky but ultimately worthwhile. Take some time to hammer out the anticipated date, make the bookings and take a deep breath and wait for her to say “yes!”


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