Valentine’s Day is the most romantic hallmark holiday of the year, so isn’t it the BEST day to propose?

No, Valentine’s Day is the WORST day to propose. I know I know you are thinking what is she even talking about? Well let me explain, it will all make perfect sense by the end I promise.

Valentine’s Day is THE romantic holiday.

So naturally, you would think that it’s absolutely the best day to propose. Love is in the air, you can feel spring right around the corner, it’s called the month of love for crying out loud.

This should be a slam dunk for the best day to propose.

From elegant red rose bouquets and hearts made of petals to bottles of champagne, we’ve seen it all. Endless displays of love, appreciation, admiration, and desire are the staple of February. 

This is the biggest proposal setup of all time. Believing that because something IS romantic that it automatically means it’s a good fit. I have news for you, it’s a trap and you should run from the idea of proposing on Valentine’s Day.

Don’t fall victim to doing what thousands of men do around the world year after year by proposing on V-Day.

don’t be like everyone else who thinks it’s a great idea to Propose On V-Day

So what exactly is the reason why you should not propose on the 14th?

It’s one of the highest proposal dates of the year, this is the day she is expecting it will happen. 

This is the day when all men across the world decide to profess their love and propose.

If you did not propose during the holiday’s changes are her radar is set for Valentine’s Day proposal.

It is the exact day that she is expecting you to propose.

But that’s not what we are shooting for here, is to be like everyone else and follow suit in mediocre at best. And we definitely don’t want to propose on the day that she is expecting it.

Your proposal is a once-in-a-lifetime event, it should be the dream surprise proposal that she doesn’t tell you that she wants.

Yes, we hear it all the time from clients how their girlfriends are ruining their own proposals by snooping around…why are they snooping around??? Because they are so excited for the moment they can’t help themselves, but ladies we need to have a talk because it’s literally killing everything.

That’s another blog post altogether.

Back to the surprise, she may tell you “she hates surprises” but more times than not it’s not the surprise she hates, it’s the knowing the surprise is coming and she doesn’t know.

The most important reason NOT to propose on Valentine’s Day...THE SURPRISE FACTOR IS GONE.

If You Choose to Propose On Valentine’s Day You Missing The Most Important Part…The SURPRISE

You may or may not have had “the talk”, she may or may not have picked out her own ring, but if you propose on Valentine’s Day there is NO SURPRISE FACTOR at all.

I have been planning proposals for over twelve years and I’m telling you women want to be surprised.  They are sneaking and they have their radar on high alert but they do want it to come out of nowhere when they least expect it.

That is the the number one thing that men say is the most important thing for the big moment, that it’s a surprise.

I’m sorry to say you would be better off crushing her heart, taking her out to dinner at a romantic restaurant to tease her, and propose on February 15th with a proposal that is fitting for what you want it to be, a SURPRISE.

Step outside the box and stop thinking that you have to keep up with the status quo on big life decisions like proposing to your girlfriend.

Choose a date that can be a date for the two of you to remember forever, not a holiday everyone celebrates.

Let’s talk about the handful of other days you should NOT propose, no matter how tempting it seems. 

1. Anniversary-Sure it seems romantic, and if I were to be honest I’m such a romantic at heart and literally celebrate every month anniversary.  But here is the thing, much like proposing on Valentine’s Day, she is absolutely expecting you to propose on your anniversary.
2. Thanksgiving/Christmas- I know there have been many studies on why the “proposal season” starts during the holiday season.  It’s the time you are about to spend with family and friends and you want to make your proclamation of love official.  But again, choose a day that is not a HOLIDAY!  Choose a day that she will always remember as the day you proposed.  When you propose it should be a date that stands alone so that you can celebrate it for years to come, this is your day. It’s a very big decision to choose a woman to be yours forever and the day she says yes should be remembered as a unique day on the calendar.  You may not want to celebrate like an anniversary but maybe a special dinner, a small gift to remind you of your dating days before life as husband and wife.  
3. Her Birthday- Clients tell me as we go through our brainstorming session together the reason for the date they chose to propose.  Obviously, I wouldn’t be a good proposal planner if I didn’t ask if their was significance to when they were planning to propose.  And more than once I have heard… her birthday??!! WHAT, why in the world would you propose on her birthday?  This is a day to celebrate her life, the years she has had on this earth and the dreams of the years to come, honoring her mother in a way of bringing her into this world and the bond they share in this day.  THIS IS NOT YOUR DAY!

Ok, I think you understand why you should NOT propose on any of those days. Let’s focus now on what day is best to propose to your girlfriend.

Yes, there are women that don’t care when you propose, if it’s on Christmas, New Year, or Valentine’s Day, they just want you to ask already, I wrote an entire blog post on that if you have been dragging your feet a bit.

But most girls, as I said before want the surprise factor and almost all of my clients say that not only is this the most important aspect of the proposal but they don’t know how to ENSURE that she will be surprised.

The answer is simple, any day other than the days mentioned above.  That is when you should propose.

I think you need to take a step back and really look at this as YOUR DAY.

You have to pull out all the stops to get down on bended knee and the spotlight is on you, what you have planned, what you came up with, and of course when you proposed.

The one question your wife-to-be will be asked over and over again after you propose is “HOW DID HE PROPOSE.”

I promise you, you don’t want the standard, oh at Christmas in front of my family, or on Valentine’s Day.  

You want her to be able to tell of an amazing day the two of you had together and she never saw it coming.

I know I promised to share the BEST day to propose to your girlfriend, so here it is.

I curated a list of the best days to propose. The benefits of choosing one day over another, and some sentimental days you probably haven’t even thought of yet. 

Download your free “WHEN TO PROPOSE LIST” to learn how to save money, give yourself peace of mind, and hit the jackpot with ideas of days that will blow her away.

How to Ensure Your Proposal Surprise is Solid

This is one of the most stressful pain points I hear from our clients. Literally, all the way leading up to the day of they are so stressed that she is going to find out.

If the surprise is spoiled and then what?

That’s the million-dollar question if I could give the same feeling to a girlfriend that found out she is being proposed to as a girlfriend that has no idea I would be a millionaire.

When she finds out it changes everything.

I know because I do this ALL DAY EVERY DAY. I don’t have a 9-5, this is my side hustle. This is all I do for a living is proposals and I’m telling you that the surprise literally shifts the energy, the emotions, and the moment on both sides.

I can’t change once she finds out, but I can tell you a few things you can do that will ensure she won’t find out.

1. Use a Different Email- Don’t even use an old email, MAKE UP a completley new email that she does not have access to.
2. Make Sure Your Phone Is Off- Read our post on how tech can hurt you to go the extra mile to ensure that you are covering all bases and that the email you just created isn’t attached to all devices.
3. Don’t Tell Anyone- Yes I know this sounds a bit unnatual but so didn’t me telling you that Valentine’s Day is the worst day to propose? I’ve heard of so many times that the secret was lost due to people that are NOT professional proposal planners and slip up.

Nothing is 100% but these are the top three things I have found when planning that are the immediate ways the surprise is spoiled.

The Exception to the Rule- This Does Not Apply To ALL Men

There is a very unique client that I have served that the surprise is not that big of a deal, in fact, there are even some clients that I’ve worked with where the bride to be knows all the details of the proposal, has chosen a dress to match the occasion. They have had full knowledge and full control of being able to get their makeup done professionally, their nails down right on time, and even have outfit changes.

This is not typical but I have to let you know that even in these rare occasions where surprise is not the most important part of the proposal we have served them where they are at with what mattered most to them.

You have to decide what matters most to you.

Remember, this is YOUR DAY, and it should reflect the two of you with some effort and a little help from a proposal planner you should be able to put together the proposal of her dreams with the surprise intact.

If you are looking for ideas on winter proposal ideas, you can check out a few blog posts we put together or you jump on a call with us and we can run through some ideas with you.