Pro: Family is all around
When you decide to pop the question during a family gathering, say during Christmas Day brunch, you can immediately share the joy with your nearest and dearest, making this moment even more special for your entire family. Imagine Grandma's face when you show her that sparkler fresh out of the ring box.
Con: Not everyone is together
Unless you coordinate gathering both families under one roof, one party may feel slighted if they don't get to participate in your engagement hoopla first hand. Working through all the logistics can be a headache and take away from the fact that it's really about your soon-to-be fiancée.
Pro: Joy abounds
Holidays are already a very festive time of the year full of little delights—adding such a momentous event to the mix takes holiday cheer to an entirely new level. Twinkle lights are all around during the entire month of December, highlighting that the celebration of your love is truly magical. What's more, you won't have to look far to find an amazing setting to get down on one knee.
Con: Holidays can be stressful (and costly)
While you may be able to save a little on the ring thanks to all the holiday sales, booking flights and restaurant reservations can end up costing you more than on any other time of the year. Most places have pricey event mark-ups and pre-fixe menus. What's more, you'll have to deal with crowds. One more thing to keep in mind: The month of December is known for non-stop holiday parties, and you wouldn't want to burn out before your own big event.
Pro: Easy to remember
You are definitely not going to forget this anniversary date—even better if you decide to get married on the same date a year later.