A Holiday Engagement? Yes, You Can!

Did you know there are six fewer days between Thanksgiving and Christmas this year?  If you’re hoping for a proposal this holiday season, we’re here to help

Here are six great tips, one for each missing day, to let you know there’s still time to make this the most wonderful time of the year… and to make 2013 a year you’ll remember forever.

#1 Ignite his festive spirit

holiday engagement

Don’t be humbug about the holidays.  If you want to get engaged soon, you have to love this season, and you must let him know. Dream of seeing that ring for the first time amid twinkling stars, roasting chestnuts and sparkly snowflakes? Tell him, in a million passionate ways.

When’s the best time to start? As early in your relationship as you can. Tell him how mushy you get around holiday times, watching kids skate, drinking hot cocoa. Let him know about holiday weddings or parties that felt really special to you.

Hailey’s boyfriend John knew she adored their town’s annual Christmas parade. “It always signifies the beginning of Christmas for me, and I couldn’t wait,” she says. So he got down on one knee right in the middle of the parade. “Many people say proposals during this season are so cliché,” she says. “For us, nothing could have been more perfect.”

How much pressure should you use? Almost none. A sales pitch will just make him nervous. You don’t have to guilt him into it: he wants to make you happy. Toss him enough clues, and he’ll know what to do.

#2 Money-smart… without going Grinch

Think talking about money is crass? Let’s go there for just a second anyway. A holiday engagement saves him money, and at this time of year, that’s a bonus he can’t ignore. An engagement ring as a Christmas present will appeal to his savvy side, so it’s definitely time for the most special kind of gift.

Should you tell him outright? You might not have to… Retailers are desperate this year, so catalogues will coming through the door all season long, it’s easy to leave them around the house with pictures circled (there may even be some great bargains).

Think beyond the obvious spots: try the bathroom, to give him the privacy to “snoop” on your secret wishes. But only circle your favorites: you might be stuck with them… Leave jewelry websites open on your screen when you step away from the computer. Stop by displays when you’re out window shopping.

If you know he wants to be responsible and save up for a nice ring before proposing, you can still get engaged now; Give him smart, fun, frugal alternatives, like the ones in this 2013 Forbes article.

A class ring or family ring can fill in until you’re both ready. Pawnshops and other secondhand sources provide fun, inexpensive jewelry you’ll always enjoy. Tara says: “I had a $10 ring for three months before I got the real deal.” She may not have had a big rock to show off yet, but the important thing was “it felt real; we really were engaged.”

#3 He cuts the turkey… YOU cut the stress

Boost your chances by making this the most stress-free holiday season he’s ever had; Michelle learned this the hard way. “I can’t be the only one who gets her hopes up around every holiday,” she says. So when she peeked at her boyfriend Jonathan’s email while he was in the shower, she was ecstatic to discover that he was planning a surprise holiday-season proposal. But when he realized what a crazy season lay ahead, with travel and shopping hassles, he put off his plans for a few months. “I wish I’d been a bit more low-key about the holiday thing.”

Make the season easy for him (you’ll probably enjoy it a lot more yourself). If he doesn’t love doing every single family event with you, pick one or two that are most important and let him off the hook for the others. Same with friends: he doesn’t have to tag along every single time you go out.

Look for ways to streamline his life. Especially if he’s super-busy at work, he’ll notice and appreciate the help. Can you pick up a gift for his mom and aunts while you’re buying something for yours? Wrap some of his presents so he doesn’t need to waste an evening doing it himself.

If you can give him the gift of time and space, he’ll feel more prepared to dive headfirst into a future with you. And once he asks, keep the ball rolling into 2014 by taking on one of these fun, fresh, engagement announcement projects.

Engage on holidays

#4 Have yourself a merry little…?

After the holiday engagement of a friend, Rachel told her boyfriend Jacob she definitely didn’t want one herself. “It’s just so predictable. I read that 20% of engagements happen in December.” (Actually, 33% of all engagements happen at this time of year).  So Jacob went one better… by proposing in September. “I was completely surprised when he proposed, and it was perfect.”

This is a complicated time of year; ask yourself honestly how much you want it. For Rachel, the answer was clear: not worth the hassle. Between travel plans, extended families, harsh weather and seasonal money stresses, it can be hard to feel romantic. You’ll be spending a lifetime together, so there’s lots of time.

There are plenty of other days ahead, from Valentine’s to birthdays to special getaways or anniversaries. That way, he can make his move without pressure and enjoy the thrill of your smile (and maybe your tears). Moments like these can create unforgettable holiday magic… any day of the year.

#5 Take time to smell the mistletoe

Ever try to hit a moving target? He can’t propose if you’re out shopping with your sisters, lunching with aunts, taking nephews to see Santa, and partying with coworkers and friends.

Slow down and make time for him. Carve out special moments – brunches, weekends, hikes, for just the two of you. Maybe this year’s midweek Christmas means you can sneak in a couple of days off to make an extra-long weekend.

When Bella set up a Thanksgiving photo shoot with Nick (here are some great photo shoot essentials), the professional snapshots captured more than just the two of them horsing around: it caught her wide eyes as he surprised her with a little box. “Inside that box was a beautiful diamond ring with two aquamarine accent stones, one on each side.” If she hadn’t made time to be with him, her holiday season might have been very different.

#6 Find the holiday joy… together

Maybe there’s a good reason he hasn’t proposed yet. Talk it out and you may discover an easy solution; Plan your next steps together so he feels like you’re a team. True, it’s not a surprise proposal, but learning to solve problems together is a gift you’ll share forever.

Abigail knew Mark worried about his grandmother’s health and was feeling depressed about the holiday season. “He thought his family couldn’t handle anything else on their plate,” she says. The couple decided the family might love a reason to celebrate, as long as they mentioned that they didn’t expect a big engagement party. The best part was telling Mark’s grandmother. “Her excitement proved that our timing was perfect after all.”

You’re a woman; thinking out of the box is what you do best; Show him a fresh way to get around the problem… and you just might strike engagement gold just in time to ring in 2014 together.


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