The Pros and Cons of Proposing During Engagement Season

The Pros and Cons of Proposing During Engagement Season

The holidays are approaching and jewelry ads seemingly make up every other commercial on TV. That can only mean one thing: engagement season is upon us. Although the tradition must have started somewhere, it feels like the holidays have always been filled with proposals. Whether you’re gearing up to pop the question yourself or you are merely ready to drop some hints to your beloved, you may be wondering if a holiday proposal is right for you. Below are the pros and cons of getting on one knee during engagement season. 


You’re among family. If getting a parental blessing is important to you, it will certainly be convenient to be able to do so and propose within the same weekend. It also means you’ll be able to celebrate in person instead of with excited phone calls. 

Built-in romance. Even if you choose a holiday besides Valentine’s Day, there will be no shortage of settings and beautiful spots to pop the question. Twinkling lights and holiday weekends will make even the most simple and sweet at-home proposal seem exceedingly elaborate. 

Meeting expectations. If your sweetheart has been patiently waiting for the two of you to get engaged, it’s likely that a lot of hopes are pinned on the holiday season. Instead of hiding disappointed, you will be celebrating! 


May seem cliché. Because this time period is known for engagements, you or your sweetheart might feel it’s not a special or personalized enough occasion for popping the question. 

Doesn’t stand out. Between all the various celebrations and the other friends and family bound to be getting engaged around the same time, the celebration for you and your new future spouse may be short lived. For some, this won’t be a big deal, but others like to enjoy the glow of congratulations from loved ones.

Not as much of a surprise. Considering that this time of year is called “engagement season,” if you want the moment to be a complete shock, this might not be the way to do it. Any walk alone or stolen moment will have your beloved waiting in anticipation. 

Watch the most romantic proposals from TV shows and get tips for shopping for an engagement ring

Opening photo for Angel Canary Photography

Authored by: Emily Lasnier