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How To Propose During The Holidays

Are you ready to pro­pose? Good for you! The hol­i­days can be a great time to get down on one knee. The cel­e­bra­tions are already in full swing, so you might as well add to the good cheer, right?

Propos­ing dur­ing the hol­i­days can be a per­fect way to cre­ate a once-in-a-life­time moment dur­ing a spe­cial time of year, as long as you plan ahead and take com­plex fam­i­ly and trav­el logis­tics into con­sid­er­a­tion. The hol­i­day is a mag­i­cal sea­son, but we also rec­om­mend try­ing not to over­shad­ow the sea­son, par­tic­u­lar­ly if you cel­e­brate reli­gious­ly.

If you’re ready to take the next step, check out our tips below to make sure it goes per­fect­ly!

bride and groom in blue suit with christmas boquet


It’s always impor­tant to have a plan for when you pro­pose, but espe­cial­ly so dur­ing the hol­i­days. When you are faced with fam­i­ly expec­ta­tions and oblig­a­tions, cel­e­bra­tions with friends to attend to, extra stress and trav­el plans, a pro­pos­al can go awry more quick­ly than hand­ing Grand­pa too much eggnog.

The last thing you want is your Mom sched­ul­ing a last-minute din­ner on your spe­cial night or a flight can­cel­la­tion get­ting in the way of get­ting engaged. Make a plan, then make a back­up plan, and clue in every­one you need to help make it hap­pen (even the flight atten­dants if need be). Just don’t spill your big news to some­one who can’t keep a secret!


If you’re buy­ing an engage­ment ring, be care­ful with it and plan ahead. It may take longer than you think to get the ring of your dreams from a jew­el­er, so leave extra time for order­ing and ship­ping. It can take any­where from 1 week to 3 months! Plus, jew­el­ry around Christ­mas­time can be more expen­sive than usu­al. Do your research and look for hol­i­day sales.

Once you have the ring and you’re mak­ing your pro­pos­al plan, think long and hard about how you will get the ring there, where you’ll keep it and how you will present it. Don’t slip it into your shorts pock­et in Bermu­da, 6 long hours before your pro­pos­al. There’s no bet­ter recipe for a ring lost in the sand for­ev­er than that. You don’t want to be this guy.

christmas ornament at wedding reception


Have you asked your future fiancé about what they want in a pro­pos­al? Some peo­ple would love to be sur­round­ed by friends and fam­i­ly as they get engaged, while oth­ers pre­fer to expe­ri­ence this inti­mate moment pri­vate­ly. Make sure you know what they want—you only get to do this once! And if you’re not sure, try ask­ing their best friend or some­one close to them (who can keep a secret!) for advice.


Chances are, you’ll be spend­ing part of the hol­i­days with fam­i­ly. Con­sid­er their feel­ings, too. Does Mom want to know in advance that you’re going to pro­pose? Is now a good time to take Dad aside to make your plans known? Should you sur­prise your fam­i­ly with the news on Christ­mas morn­ing? Think about how you’ll involve them in your plans and break the news in advance so every­one is hap­py come the big day.

Good luck if you’re plan­ning on propos­ing this sea­son and con­grat­u­la­tions!

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