50% of all engagements happen between Halloween and Valentines Day. Okay, I just made that statistic up, but its pretty darn close! So many people get engaged during the winter months, and its a great time to do so! Family gatherings make for a great way to annouce the news to several people at once, there are great parties already, now just excuses to bust out that good bottle of champaign!
My advise on engagements over the holidays... don't put too much pressure on the two of you. It doesn't have to be this big ordeal to stress you out over the most stressful time of the year. Keep it low key, and if you decide to announce it later, that's fine too.
If you do get engaged these months, be sure that you will get tons of questions... When's the date? Where are you getting married? Just know that everyone's thinking "What does this mean for me"... Be prepaired for somewhat of a generic answer... "Summer - somewhere in Portland!" Or "Fall, and at the beach." At least they can start thinking about travel plans and what it really means for them to be a part of your special day.
Have some plans skeched out? Let them know, but if not, no big deal - just be sure to GET THEIR ADDRESS! That way when the details become a little more clear, you have a way to mail them, or email them the Save The Date - you'll want to get this out at least 4-5 months in advance if people are planning travel. Collect their address at the holidays, at least you have one less thing to track down!
If you don't get their address in person, or would prefer a little more automated way of doing so, I am a big fan of Google Forms... As long as you have an email, or facebook connection, you can send them a link and then they get to fill in their own address! You can even add "How likely are you to attend our June 17th Portland wedding?" That way you can get a rough idea of how many people may actually show.
Engagements are fun! Make the most of it, and have fun on this start of the journey together. Don't get stressed over this, but go all out if that's what makes you happy! This is the Forward to the story of your lives together. Big or small, engagements start an adventure with your best friend.
Wishing you all Happy Holidays, or a Married Christmas!
Will & The DMWTB Team.