Know your S.O.'s personality
This would seem like a no-brainer, but it's easy to get so wrapped up in the proposal itself that you completely forget whom you're dealing with and that she detests public displays of affection. "Not only do some people not want to share an intimate moment in front of other people, but they also might feel pressured to say yes," says Post. Should the proposal (gasp) not go as planned, a holiday can also be an opportune time to erase the memory and celebrate something fun instead, she says. But hopefully, by now, you and your partner have already had that "check-in" about a future together, so a proposal wouldn't come as a complete surprise, she says. If your S.O. would be totally into a public engagement, than a proposal on Christmas Day or New Year's Eve could be a really special way to share the news in the company of friends and family, says Post.
Assess the situation beforehand
So maybe you do know her inside and out, but have never asked for her opinion on this topic (so there's one thing you haven't covered). While you don't want to blurt it out and ruin a potential surprise, you can sneakily bring it up in the context of other people. Try to gauge her thoughts by mentioning someone else who got engaged during the holidays: "What do you think about Joe proposing on Christmas?" Or, consider asking her loved ones. "It's probably a good idea to run a proposal by her family if you're planning on doing it while visiting them," says Post. Plus, you'll also want to make sure they are ok with sharing the holiday with your special moment.
Find another day to pop the question if the holiday also falls on a family member's birthday
Your sister has (reluctantly) shared the day of her birth with Christmas for her whole life—and has never stopped letting your entire family know just how she feels about getting the shaft where presents are concerned. So, imagine her state of mind if she had to divide her thunder into a third with an event that will trump everything else, says Post. Enough said.
Ask during a private moment within the party
If your S.O. is the type who would rather have a root canal than show any PDA, you can still propose over a holiday to make it a special occasion, but just don't do it in in front of a crowd, says Post. "There are lots of little ways to make the moment personal even in the midst of a big New Year's Eve party," says Post. Step outside the party, go for a walk—do whatever it takes to be alone.