The Best and The Worst Days To Pop The Question (yes, there are “bad” days)

Last month, we talked about how planning your proposal on Valentine’s Day is one of the worst days to select. It’s pretty obvious we’re against February 14th (if you didn’t get a chance to read it, check it out here)- the question is, are there other days that you should consider when proposing to your girlfriend? 

The answer is an absolute yes. The “When” shouldn’t just be a day that is convenient for your schedule. The day you pick for your proposal will be a day you both remember forever. This means you need to really put the effort into looking back at your relationship and think about the days that have meant the most to you thus far.

Think about all those firsts the two of you had together or a day you just can’t forget. The date you pick for your proposal doesn’t need to be the biggest moment of the relationship; it can be any day you simply felt happy together. You need to be able to find the balance of selecting a random date, so she is surprised, while also choosing a date that has some sentimental aspect to it for the both of you.

The perfect day to propose to your girlfriend is out there, I promise. You might not know it yet, but that’s why I am going to tell you exactly how to go about choosing the best day to propose to your girlfriend.

Let’s start with when NOT to propose to your girlfriend

Obviously, Valentine’s Day. In case I haven’t made that clear yet: DO NOT propose to her on Valentine’s Day. You might as well wave goodbye to the surprise factor, considering V-Day may be the most obvious date for a proposal. 

There are three other dates alongside Valentine’s Day that are absolute no-gos. Do people still choose to propose on these dates? Of course- at the end of the day, it’s YOUR proposal and it will be a day to remember regardless. Do we agree as proposal planning experts? Absolutely not. 

One of the biggest things our clients tell us is that the most important thing in their proposal is the surprise factor. In order to protect that surprise, the DATE has to be a surprise. When planning a proposal, you will find that it almost feels like the world is working against your efforts to keep the surprise. From tech to the cover-up, we know all about the risks AND how to counter them, explained in our blog post about surprise proposal planning.

The best way to protect your proposal secret? Don’t pick a date she would expect to be proposed on.

Perhaps there’s some sentiment behind them, but I promise there are other days that will make your proposal even better. 

Here are the top 3 dates that you SHOULD NOT propose to your girlfriend:

1. Your Anniversary. Cue the romantics- what better way to propose than on the day that already means the most to you both? I’ll give you the answer- there are TONS of ways to propose that would top an anniversary proposal. Much like Valentine’s Day, the surprise factor of the proposal is totally gone. She absolutely expects you to pop the question on your anniversary. Instead, treat her to a nice dinner for your anniversary of course, but consider waiting until a couple of days after your anniversary to propose to her. If it didn’t happen on the day of, she definitely won’t be expecting it a few days after. 

2. Thanksgiving/Christmas. I know, I know. I’m guilty by association. My dad proposed to my mom on Christmas Eve nearly 30 years ago, and they are still madly in love. So who am I to say don’t do it? It does seem like the perfect time. You’re around your family and friends, celebrating your blessings and the people you hold close… 

The truth is, as tempting as it may seem, it’s so PREDICTABLE!! 

Of course, it would be the perfect time to propose! 

But, as I’ve said already, the surprise factor is so important to so many women that you really need to think about who this woman is that you’re asking to marry. If her dream proposal is in front of a Christmas tree, surrounded by family, give the girl what she wants. 

Just remember that the most asked question she’s gonna get when people see the ring is:

 “How did he propose?”. 

Let’s create a proposal with a better response than “In front of my parent’s Christmas tree” or “He made a toast at Thanksgiving dinner”.

3. Her birthday. Guys. This has got to be the hardest one to hear. 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 on this day.  THIS IS NOT YOUR DAY! There are 365 (sometimes you even have an extra day in there) days in a year- her birthday is the one day a year she has to truly celebrate herself. Not only would it take away from her day, but it also wouldn’t have too much meaning behind it. 

Your proposal day is something that will be remembered for the rest of your lives- it should be a day full of passion and happy memories of you both together, not necessarily as individuals. After all, it is the day that marks the start of the rest of your lives together.

Now, we can discuss what days are best to propose to your girlfriend

The key to choosing the best day to propose to your girlfriend is to look at it as YOUR day. 

From day one, you have to do all the planning solo, be creative, be romantic, be clever, and get her dream ring and present it oh so perfectly. No pressure, right?

WRONG! SO MUCH PRESSURE! Which is exactly why we cannot tiptoe around the fact that it’s your big day, so let’s make it a day you want to remember as a stand-alone celebration. 

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 simple answer to when you should propose to your girlfriend? Any day other than those mentioned above.

By creating this day from your heart and making it yours, it’ll be easy to ensure she is surprised with her dream proposal. When her girlfriends and family ask how you proposed, she’ll have a magical, emotional story to tell that ends with “I said yes”. 

If you’re looking for more tips on what women want in a proposal, check out this blog post. 

Want to dig deeper into the best days to propose to your girlfriend? From the best days to even the best times, we have also curated a special guide available for download that gives you everything you need to know about when you should pop the question.

Just propose to your girlfriend already!

Of course, there are women who don’t particularly want the surprise factor, or to some, even the proposal itself might not matter too much. Although it may seem contradictory to everything we’ve been telling you about selecting your date, you need to understand that not all women are the same with how they see their dream proposal (if they even have one). 

You know your girlfriend the best, so you need to take the time to really see her for who she is and what she wants.  

• Some women want you to just ask already. These ladies just want to scream “YES!” from the rooftops already. If she’s been showing you pictures of rings for quite some time, or even better, talking about wedding venues… I’d recommend putting some pep in your step. Women aren’t fans of those who drag their feet; when we know what we want, we know and want it as soon as possible. 

Of course, it’s important to ensure that you’re both ready before popping the question. Sit down with your loved one and have a conversation. Talk about the future you imagine together and how happy you two make each other. By doing this, you can both be 100% confident going into the proposal. And, it will be the happiest “Yes” of your lives. 

• Some women, by nature of culture, KNOW all the details. They have a dress for the proposal, perhaps even outfit changes. Some women get their hair and/or makeup professionally done. It’s important to really understand your girlfriend and how she imagines her dream proposal. 

Don’t forget about traditions involving wedding proposals, such as asking her father for his blessing. While this may seem outdated, if your girlfriend’s family is more traditional, having that conversation shows your respect for them and their daughter. What better way to start off the soon-to-be marriage than with a good relationship with her family?

Celebrating your Proposal Day forever

The date you propose to your girlfriend will be one of the most important, memorable dates of your life, and more importantly, the life you’ve officially started to build with your now-fiancée. Some couples still post “Happy Proposal Day” years after the engagement. 

It’s important to remember that there are other factors of your proposal that are incredibly important, such as the ring itself (DUH right?), the physical location of your proposal, and even the finer details such as the design concept and the speech you prepare. 

Be sure that these items aren’t overlooked. Take our advice above to create the perfect proposal that your girlfriend is sure to brag about. If you’re still looking for more tips and guidance, check out our blog here or book a call to chat with us.

The most important thing is that your proposal reflects the two of you.

Everyone has different preferences, and every couple is unique. There is no “perfect date” that I can give to you; I can only relay the best advice to guide you. Remember to reflect on who you two are as individuals, and as a couple, and plan your proposal to show how special your relationship is (and future marriage will be!).