Engagement Over the Holidays

As if Thanksgiving, Christmas, Hanukah, Kwanza and New Year’s Eve weren’t enough, wedding engagement season is in full swing with a flurry of holiday marriage proposals, ‘Tis the Season to Get Engaged.  Wannabe husbands bend a knee and pledge their love to their one and only love.

Remember, you just need the question and a ring.  But finding a way to make it extra special is part of the fun of this.  Think about places that mean something to you as a couple, or to you or her personally.  Should it be something she finds?  Something you hold out to her?  It can be something as easy as ensuring a specific song is playing

More than 30-40% of couples get engaged over the holidays.  The most popular times to pop the question:

  • Valentine’s Day – A bit obvious and in my opinion a little to predictable and lacking in originality.
  • Christmas Day – A great time because it saves you having to call all your family and friends to tell them. Makes a pretty good Christmas gift and you’re guaranteed to never forget when you got engaged.
  • New Years – Another pretty fun and unforgettable time to slide a ring on that special person. New Years Eve always has such a build up and a lot of times end up being a let down. Popping the question could take it to a new level. Just be sure that you don’t party it up too much.
  • Anniversary of the first date  – This is a good one and special because it is all about you and your spouse to be. Make sure you have the right date.
  • Girlfriend’s Birthday  – This is still really popular. Don’t be cheap and try to get away with not having to buy a birthday gift.
  • Any day that works – Somehow over time, couples have instinctively known when the time was right.

Knowing your engagement is coming is no fun.  Even if you’ve discussed getting engaged before, find a way to make it a surprise.  Take care to throw her off your trail and keep those who know about it on the down low. The minute those words are spoken, the world shifts.   Make that moment just right and you will have a winning proposal.

Once you’ve popped the question and the sparkle is on her finger, she’s going to be showing it off.  If you can arrange it, get her Mom, sister or friend to take her for a manicure a day or two before the big moment.  You’ll have to find a way to make it not a big deal so she doesn’t suspect, but post-question she’ll be stoked she has a perfectly manicured hand to hold that ring up with, and she’ll be touched you thought of it.

If you want to take it a step further, keep in mind that no woman pictures this moment with bad hair, or a frumpy outfit on.  Take care to make your plan work for a time when she has maybe put some special effort into the way she looks.

As much as this moment is all about you and her, it quickly becomes about so much more.  You are making a move that will join two families.  If asking for her Father’s blessing (or both parents) is something that would be important to her family, then do it. Whether you agree with the practice or not, it is a sign of respect and will make your path to becoming a member of her family much smoother.   If you are too scared to do this small task, you aren’t ready to get engaged.

Think carefully about your fiancé and your own relationships with friends and family.  How does she behave in public?  Is she open with her affection or is that reserved for when you are alone?  If you are planning a public proposal, you want to be sure she will be comfortable with it being on display with others watching.   Especially if you are planning to do it in front of family, who will quickly swoop in with congrats.  If you want more of a quiet and private moment, make sure you arrange for that setting.

Have a camera ready.  Take a few shots after you’ve both calmed down a bit.  The joy on your faces is something you’ll want to capture and remember.   Your cell phone just isn’t going to cut it.

This is huge news, so take care with how you spread it.  Just like I said before – this is bigger than the two of you.  This news is about your parents, siblings and friends too. Don’t update your status on a social network before you’ve personally told those who deserve to know first.  Tell your parents or closest loved ones first – if you have to, call them.  They deserve to be the first to know.  Then move on to siblings, other close family members and very close friends. Keep in mind that with this announcement comes a lot of questions.  If you want to keep it to yourselves for a few hours or even a few days, no one would blame you.


  • Look your best for any potential proposal outing if you care about how those first engagement photos come out.
  • Bring holiday cheer to your family gathering and announce that you’re engaged for the group.
  • Don’t make a big announcement if anyone in attendance may be sensitive to the issue of engagement.
  • Don’t share your news online until you’ve told your family at the holiday gathering.
  • It’s ok to wait until New Years to tell everyone also.
  • Think about when you’d like to get married. That question will definitely come up at family holiday gatherings.
  • Don’t feel bad if the Christmas or Hanukkah gift you got your boyfriend doesn’t match up with the engagement ring he bought you. He knows you wouldn’t have gotten him socks if you knew an engagement ring was coming.
  • Do get your guy a nice engagement gift once your budget’s recovered from buying gifts.
  • Don’t expect an additional holiday gift.
  • Don’t throw an engagement party before the New Year.Your friends already have a billion holiday parties they’ve agreed to attend, and they’ll need more notice than a few days.
  • Don’t take it personally if your friends don’t text you back after you tell them your news on Christmas Eve or Christmas. This is the one time a year that everyone should have extra slack dealing with each other.