'Tis the Season: A Holiday Guide to Your Engagement

Massachusetts Wedding Photography by Ryan Richardson Photography

Winter in New England is a pretty quiet time for weddings. Snow has fallen over the ground, casting a beautifully serene blanket over the earth.  It's a time of year where we try to forget the world outside by turning inward toward our friends and families, bathing ourselves in the sunny glow of holiday parties and good cheer.

It might not be the time for weddings, but winter is the season for engagements. According to The Knot, most couples get engaged sometime between Thanksgiving and Valentine's Day. And what better time is there? The long nights are perfect for a little romance, and it's rare to have so many people you care about gathered in one place to celebrate the triumphs of the year past and the road that lies ahead.

Also, the non-stop ads for jewelry certainly help to bring the conversation toward engagement rings.

So while everyone else is popping champagne corks, a few are getting ready to pop the question. As a wedding professional I've heard of everything from happy endings to horror stories, and to help make sure the answer is yes (and to make sure that I still have weddings to photograph) I've come up with a few tips.

Paving the Way to Popping the Question:

If romantic comedies have taught us anything, it's that women often lead the way to the altar. Of course it's not always as obvious as a countdown clock and an ultimatum, but you can see little hints of interest all around.

5. You find that sunday nights are increasingly devoted to marathons of Say Yes to the Dress

4. Your girlfriend experiences a sudden interest in tulle

3. Those longing glances at the jewelry counter

2. You've been to more than one of her friends' weddings in a year

1. Your visit to city hall "accidentally" winds up in the line for marriage certificates rather than parking permits.

Not everyone is cut out to be a romance detective however. Men especially can miss subtle signs and emotional cues, especially when they're not on the lookout. I've met with several couples who have found great success not through hints, but through conversation. Treat your partner like a partner and aask them how they'd feel about getting engaged. It might take away some of the surprise but maybe this won't happen to you...

The Ring is the thing:

Once you've made up your mind to propose, you're going to need a ring. Tradition (made up whole cloth by De Beers in the early part of the 20th century) says that an engagement ring should work out to about three months wages, but the average engagement ring cost approximately $2,100 in 2007. Increasingly couples are purchasing their engagement rings together, which means you will get the style and fit right the first time, but lose the element of surprise.

If you want to surprise your fiancée with a ring, there are two things you'll need to know. Her taste in jewelry and the size of the ring finger on her left hand. For the former you just need to watch what she wears and what she looks at the most (a trip to the jewelry store for a necklace or a bracelet with her is all you need).

Sizing is a little trickier. It's not like buying a sweater where you can ask about her size without arousing suspicions. Your best bet, if she has other rings is to get them cleaned for her as part of a gift, while they're being cleaned you can get the right size (though there might be minor variations between the size of fingers on the right and left hand).

A Clever Plan:

A good proposal needs to do one thing above all, make your partner feel like the most special person in your world. Often, the traditional route of a romantic evening and getting down on one knee is enough to make that happen. There are as many right and wrong answers to this question as there are brides, but try and avoid making an attempt at a viral video unless you know for sure your fiancée wants to be a 15-second Internet celebrity.

Public engagements can make your would-be fiancée feel pressured or nervous, which is a poor foot on which to start. If you want to make a public gesture, speak to her about it ahead of time and let the time, place and method be the surprise.

Making the event memorable is even easier if you turn your romantic evening into a surprise engagement session. With a little planning you can have the exciting moment captured for a lifetime with one of our portrait sessions. It's a great way to start off the wedding planning that inevitably follows. Above all, you know your partner best and when planning your proposal keep her hopes and dreams in mind and make them your own.