Holiday Proposal Dos and Don'ts - Proposal Advice - Engagement Ideas

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Proposal Advice

Holiday Proposal Dos and Don’ts

How to sidestep 10 potentially embarrassing pitfalls.

Photo: Todd Rafalovich

At first glance, holidays seem tailor-made for marriage proposals. Families are gathered, the atmosphere is magical (who can resist twinkling lights and newly fallen snow?), and it’s big-ticket gift time. But the truth is, popping the question this time of year is a high-stakes move. If all goes well, viola -- another happy holiday memory. Not so well? (Gulp) Let’s just say it’ll be harder to forget. Want to improve your odds? Read on.

Do: Make sure you’re really ready to propose. Are you asking her because she’s the love of your life? Pass. That's a great reason to get engaged. Just couldn’t think of anything else to give her for Christmas? Fail. Buy her an iPod and keep moving.

Don’t: Sip so much ’nog to quiet your nerves that the proposal comes out, “Hey (hiccup)…d’ya wanna get married?” Be sure to curb your festive drinking so the moment you pop the question is remembered as a special one. Don’t forget: The story of how you propose will be retold for years to come!

Don’t: Do it first-thing. The proposal should be the high point of the holiday. Christmas? Let the ring be the last gift she opens. Hanukkah? Give it on the eighth night. Imagine: It’s morning, she just said yes, and now she’s got to act psyched about opening the mock-a-socks from Grandma? Uh-uh. Mock-a-socks first, diamonds second.

Do: Consider giving her parents a heads up if you think they can take it. While asking for her hand in advance is a charming move, if you think they’ll drop hints, project weird, nervous energy (think: pacing or Cheshire Cat grins), or otherwise distract from the traditional festivities, you might want to skip it.

Do: Remember to be yourself. Resist the urge to channel her favorite rom-com star by reciting someone else’s lines, unless being openly laughed at by the woman you love is your goal (we thought not). Remember, this moment is about you -- you and the person you hope to marry. So be yourself.

Do: Consider how private she is. Is your (hopefully) soon-to-be fiancee an extrovert who tweets the most intimate details of your relationship (and just about everything else!) to her 3,000 followers? Or does she put the “P” in private? Former? By all means, go forward with your plan involving The Rockettes. Latter? Maybe breakfast in bed (with a side of bling) is more her speed.

Don’t: Steal someone else’s thunder. If her mom hands her dad the keys to a brand-new car or her brother comes home on surprise leave from Afghanistan, sit back and let them have their moment. Don’t barrel on through as planned. Wait until the squeals have long died down and everyone has moved on before announcing that there might be one more thing to celebrate.

Do: Consider your audience: Dropping to one knee in front of her parents’ tree could get you great results (think: tears of joy and heartwarming toasts) or it could mean getting heckled by her druncle (you know, her perpetually drunken uncle). Do a little recon mission in advance to be sure it’s a proposal-friendly crowd.

Do: Leave a little room for spontaneity. Say you’ve got a rock-solid plan to propose on New Year’s Eve, but spot her tearing up during It’s a Wonderful Life. How about giving her the ring (along with that Kleenex she asked for) right now? Bottom line: Allow inspiration to strike.

Don’t: Go nuts planning a gigantic holiday production (read: multiple singing Santas). Here’s the deal: Asking someone to marry you is plenty special on its own. Sure, adding hyper-unique elements can be fun, but necessary? No. Keep it simple.

-- Hallie Goodman

See More: Engagements