Top Ten Do’s and Don’ts For Planning the Perfect Holiday Proposal

The holidays hold special memories for all of us and for some lucky ladies, it will be made extra special this year when the love of their life gets down on bended knee and proposes marriage. December is by far the most popular time of year to propose (with the months of May and July at a far second). And, not to add pressure to what you are already feeling gents, but getting the ring right is the first and most crucial step to a perfect engagement.



Your Mission


If you want to get engaged this holiday, remember that many girls spend their whole lives dreaming of their wedding day and having the most romantic proposal story that they will be able to tell their friends, family, co-workers and grandchildren for years to come. Having the element of surprise is very helpful. ‘Leave no trace’ should become your mantra, as you sleuth and plan like a gumshoe detective on a mission to plan the perfect proposal.


Here are my Top Ten Do’s and Don’ts For Planning the Perfect Holiday Proposal


  • Don’t tip your hand. Only tell a few trusted confidantes and family members. Seriously. You don’t want the word to get out. For the next few weeks you should act like Agent 007. A little theme music may help.


  • Do clear your browser history. Leaving your computer open with engagement ring websites in full display will give your game away. And above all, as they say, you got game.


  • Don’t forget her personal style. From improper ring fit to a diamond or style she doesn’t like, doing your recon on her ring is imperative. Make sure you know the diamond shape she loves (do not guess!) She may love a sparkly band with a halo around the ring, or she may want a simple solitaire diamond on a gold band. Two completely different looks so do some digging.


  • Do take advantage of a family gathering. Because most families are together during the holiday season – one side or sometimes both – it does make a Holiday proposal easier, as no one has to make travel arrangements. The first thing women do once they are engaged is call their family and friends so it is ideal to have them already there celebrating Christmas or Hanukkah.


  • Do separate family time and the actual Holiday proposal by planning a day or overnight getaway somewhere close by. Do you both love to ski? Take her on a Christmas skiing trip and propose on a mountain top in Aspen. Are you always stuck in city traffic in the neighborhood where you two plan to call home? Contact the highway department and instead of having the lit-up highway sign display a message about the treacherous road ahead, arrange to put up your proposal in writing. Every time she drives past it, she will remember your proposal and the best Hanukkah, ever. Once the proposal is sealed you can drive back and celebrate with family. Or have them waiting in a nearby restaurant for you to join in for a toast!  So be creative and have fun! Enjoy the proposal and do whatever you like, just find a way to involve the family so they can celebrate with you.


  • Do consider fun Holiday proposal ideas, such as:

           Hiding the ring in the mistletoe, give her a kiss and tell her to look up….

           Hiding the ring as a stocking stuffer…

           Build a Snowman Together and put the ring on Snowman’s Hand…

           Wrapping your ring in a big obnoxious box that has a small hidden surprise in it…


  • Do choose the right stone. Round brilliants are the most popular stone choice by 70%. If you aren’t sure what shape to get her, that is the safest bet. However, choosing a shape that embodies her style and personality is an integral part of the selection process. Just like we are selective about our shoes and handbags, wearing one ring for the rest of our lives creates more importance on getting this selection right. Cushion and Oval cuts are very popular and also timeless. They have significant sparkle and brilliance. Emerald and Asscher cuts are more understated and classic. A ‘less is more look, if you will.’ Shapes like heart, pear, marquise and Princess are very specific taste so make sure she requested that shape before you buy it.


  • Do consider something aside from a diamond. Perhaps she has expressed the desire for gemstones instead. Sapphires, Rubies and Emeralds are a beautiful option. Sapphires and rubies are the safest gemstone option for an everyday ring since they are a 9 on the Mohs scale of hardness (Diamonds being a 10 and Emeralds being a 7.5).


  • Do remember that no matter what people have told you, size matters. When it comes to engagement rings, unfortunately for men’s bank accounts – size really does matter. For many girls, the size of their engagement ring is a really big deal for them. She will be wearing it on her hand for the rest of your lives together (hopefully). Obviously each girl is different in what their expectations are but you need to know what your girlfriend’s expectation on size is – and hopefully surpass it!


  • Do consider using a ring concierge. The purpose of a ring concierge is to help you access top quality luxury selection at a non-retail price. A ring concierge will know how to help you customize her setting and personalize her ring so she will cry tears of joy (not disappointment) when she sees what you picked for her.

Michelle Rielly is a Beverly Hills based “Engagement Ring Concierge” who works with Celebrities and High Net Worth Individuals to find them the perfect ring for their future bride. With over 10 years experience working at the likes of Harry Winston, Tiffany & Co.,and Van Cleef & Arpels. she has the inside track to all the jewelry dealers around the world to helps her clients find the best ring at the lowest price.


By Michelle Rielly

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