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Engagement Season

It is Engagement season! The evergreens, scent of pine, cinnamon and cloves combined with twinkling Christmas lights usher in all the romance feels.  Here in Virginia, our Decembers are pretty mild for the most part, even with a little chill in the air.  Planning outings outdoors with the love of your life, such as taking a stroll in Colonial Williamsburg, is fairly easy, convenient, and offers a variety of options….especially when you are planning to propose to your significant other.  Making an intentional plan will help you to pull off the perfect proposal that you will both remember for the rest of your lives. 

Let’s get started.


Having a conversation with your soon – to – be Fiancé’s  family is very important, especially if you want to have a positive relationship with them after you pop the question.  Family is important and it will mean a lot to them to include them, if possible.   There is something to say for marrying into a family.  You may not live with them, but building a positive, healthy relationship (which includes inviting them into knowing your intentions and plans) will have ripple effects for your future and your children’s future.   They may also have some great and meaningful ideas to offer as well which could really help to make it memorable and unique. 


Decide on a ring budget.  Researching the cost of rings that your future fiancé would like will help you as you decide on what to purchase for the love of your life.  I highly recommend doing your homework on this.  In addition to researching pricing, it is also valuable to search for reliable jewelers, and have a good idea of what your future fiancé likes. If you are not exactly sure what she might like, enlist the help of her family and friends.   In order to pull off a great surprise, it will be helpful to know her ring size as well.  Go here to learn about ways to get her ring size without her knowing.

It also is important to decide on a budget for your proposal.  Will you hire a photographer?  Will you buy her dinner at a 5 star restaurant?  Or will you pop the question at a favorite location and then celebrate with family afterwards? 

Location and Season

Choose how and where you will propose.  Your proposal should be unique to your relationship.  There are so many “viral” ideas out there that may sound amazing.  However, if the idea does not connect to who you are as a couple, it may fall a little flat.  Consider meaningful locations, such as where you met, a favorite location where you like to bike or walk together, or the place where you first said “I am in love with you.”  Consider the time of year as well.  

Christmas is a time when families often gather together.  If Christmas season is a time that is meaningful for you as a couple, it could be a great opportunity to pop the question knowing that family from out of town could be there to celebrate afterwards.   Or perhaps you want to propose when it is warmer outside when walking on a beach or at a park, for example, would be a little more comfortable. 

Time of Day

Time of day is really important, too, especially if you plan to hire a wedding photographer like myself to capture this beautiful moment.  As a photographer I can consult with you about the best window of time for natural lighting.  I will also be able to coach you on exactly where to stand and what direction to face so that I can capture the moment without obstruction of view.  After you propose, I offer a post proposal session to clients.   Couples can opt to use these images for their engagement announcements as well as printing on canvas, metal, or a coffee table book.   

A little advice from your cheerful wedding photographer:    Make sure that you provide an excuse for your special someone to dress up.  Everyone is different with this.  Some ladies do not mind having images taken when they haven’t put on make-up.  That is perfectly fine!  If your girlfriend is more selective about her appearance for photos, the experience will be more pleasant for her if you provide a believable excuse for her to get dolled up.

Choose What You Will Say

While what you say will be really important, don’t make this too complicated.  Do you need to write and rehearse a 3 page speech about your undying love?  I am all for romantic accolades. (Hallmark channel junkie here!)   Perfectly crafted poetic words are lovely, but keep the message authentic.  Your words should convey a beautiful message of love in a genuine way.   The big thing here is to be yourself; be creative in how it fits your relationship while being you.  Then, pop the question! 

Now it is time to celebrate!