Pros and Cons of Proposing on a Holiday

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“My most brilliant achievement was my ability to be able to persuade my wife to marry me.” ― Winston Churchill

Every guy is looking to make his wedding proposal extra special. You already chose the perfect designer engagement ring that she will be sure to love; now all you have to do is find the right moment to get down on one knee. And you’re probably thinking how romantic it is to get engaged on Valentine’s Day, or wouldn’t it be a Christmas miracle if I popped the question on Christmas. Wrong! In most cases there are more cons, than pros, when it comes to proposing on a major holiday.
A. JAFFE has made a list of all the reasons why you should steer clear of February 14th, December 25th or any other major holiday.


Some people refer to proposing on a holiday as the “kiss of death” You don’t want to start off your new married life in that direction, now do you? When it comes to popping the big question you need to think of the big picture. What will this day mean years down the road? And what will happen if you don’t get the outcome you were hoping for? It might seem like a romantic idea today, but that might not hold up forever.

If she says no or the engagement is broken off this holiday will be a personal reminder to the both of you. Each year when the snow is falling, Christmas lights are up, and everyone is happily sipping on spiked eggnog; you or your ex might be sobbing over the past. Each time your heart will be breaking over and over again. It will go down in history that the holiday you once thought would make the perfect proposal is now a day of misery.
Everyone loves any holiday. Holidays normally mean presents, eating, drinking, and happiness. So why not add a special holiday to the calendar, your engagement. No girl wants to share her special day. By choosing your own special day for a wedding proposal, the two of you can have a yearly celebration remembering that special moment.


Lastly, the holiday can be very stressful for some people. There is so much hustle and bustle you wouldn’t want to ask your sweetheart to marry you when there is a lot on her plate. She is probably already stressed out, no need to add the thought of planning a wedding to that.

We realize not everyone will have a bad experience with proposing on a holiday. Some couples have great success. This is where the pros of a holiday wedding proposal come in. Now there is an added sense of significance to the day. Christmas, Valentine’s Day, New Years Eve, etc. has become extra special for a happily engaged couple. It is a very consistent time of year filled with joy and cheer. There is an exception to every rule and some women feel honored to share their special day with some of the most iconic holidays of the year. One thing is for sure; it will sure be a memorable day!

The choice is yours when it comes to popping the question. If you think a holiday proposal is going to be a success then go for it. Just make sure you are outweighing the good from the bad. It’s not the date that needs to be special; it’s how you go about kneeling down, pulling out that perfect A. JAFFE designer engagement ring, and popping those four little words, “Will You Marry Me?”


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-Posted by Caitlin Fischer

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