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The Ten Top Proposal Mistakes to Avoid

outdoor proposal location
Photo by: Golden Hours

Saving You From A Possible Proposal Disaster

We know that for men who are proposing, their number one fear is making a mistake during their proposal. 

Not knowing if what you planned is perfect can always be intimidating, especially because you want to make it the best for that special someone. Well, lucky for you, we here at Visions know a thing or two about proposing and how to do it right. 

While we can’t predict what will go wrong, we know the most frequent mistakes and how to avoid them. I’ll give the disclaimer that every couple is different, so something that you want to avoid might work for someone else. However, these are generally things that are a no-go all around.

Not Asking For Her Hand

As cliche as this may sound, many of our clients would not dream of proposing without first asking for her hand.

I know it may seem super old school but for us, this proposal mistake is a huge no-no, especially for couples whose culture strongly suggests it.

Even if your culture is not big on asking permission we still highly recommend that you do it anyway.

Taking the initiative by asking permission to marry their daughter will go a long way. This will show that you are looking forward to your family joining together as well as showing due respect to her father.

How to Plan the Asking

In regards to how you ask for your partner’s hand, the circumstances need to be completely separate and should be a step in planning your overall proposal. 

When asking for your girlfriend’s hand, it should be a different visit than any other routine time.

Unless you’re super close to your future father-in-law, wanting to go somewhere and talk with him will be a big indicator as to what you’re doing. 

My suggestion would be to, if you’re able, make it a day trip by yourself. Enlist help from other family members of hers so that you can talk to her dad without your partner knowing.

The only thing that is a must is secrecy. She should have no knowledge of you doing this in order to make sure that your proposal timeline isn’t compromised.

Picking a Random Location

Another proposal mistake I would advise against is not putting thought into your proposal location. To put it simply, location is everything. 

One of the number one things we hear from clients about choosing a location is that they don’t want it to feel random. We completely agree.

It should not only be a gorgeous backdrop for photos, but it should have some significance within your relationship. If it doesn’t, it can feel disconnected and not thought through. 

Take these tips into consideration when making the choice of where to pop the question: 

If you’re sentimental, like me, consider using the location of a first date, or a major marker in your relationship. It shows attention to detail and creates a nice memory to add to the old one. 

Not to mention, many of our clients are long distance. By proposing in the city that she lives in, you’re creating a core memory of the two of you together and gives you something to reminisce on in the future.

Another way to choose is to look at what represents you as a couple. Are you foodie-type people? Do you appreciate museums and art? Or perhaps you like to spend a lot of time outdoors. 

Either way, the location of your proposal should reflect the two of you and the things you enjoy doing together.  

Choosing a venue is a huge part of the proposal planning process, so take your time with it, and get it right.

Remember the When

Another big decision for the setting of the proposal is when to do it.  The timing on that special day is extremely important. When we help our clients plan their proposals, we always suggest getting down on one knee around the “golden hour”. 

The golden hour is that time right after sunrise or before sunset when the sky is all red and pink. It’s also around the time when all of the lights in the city come on, which brings the city to life in the background. 

I would plan to propose a bit before that golden hour hits so that you have those beautiful lights and colors in all your photos. 

Trusting the Weather

On top of your ideal proposal location, you also need to have a backup plan. In case you didn’t know, Chicago weather is some of the most finicky in the U.S. Just in the last few weeks it’s felt like both spring and winter with the amount of rain and snow. 

What does this mean? Well, it means that you absolutely need to have a rainy day plan. 

Whether it be a primary location that shields the elements, or a secondary location that, at the bare minimum, has a roof, you have to make sure you have a plan. If you don’t, the weather in itself has the ability to ruin your proposal. 

You might think that proposing in the rain could be a fun memory for you and your partner, but it won’t be. You’ll remember how chilly and wet you were, rather than how happy proposing made you both. 

man and woman looking at one another
Photo by: Golden Hours

Bringing Her to the Proposal

This is honestly one of the biggest proposal mistakes we tell our clients not to do. I know this might not make sense, but stick with it. There’s a method to my madness. 

You might not think so, but there is such an immense amount of pressure that comes with bringing your girlfriend to her own proposal. Instead of being there, in position, thinking about what to say, you’ll be thinking about her reaction.

I’ll tell you, the build-up between her arriving and you waiting is only half of the feelings and emotions. Having her come to you produces a 100% authentic reaction unlike any other. You already feel giddy that the moment you’ve been planning for is about to happen. But the emotions you’ll feel when your eyes meet are so intense and can only be done with her meeting you at the scene. 

What Happens if You Bring Her?

So what happens if you’re the one who brings her to the proposal?

You think you’re being suave and secretive about where you’re taking her. You’re probably thinking “no one’s going to know. She’s not going to know,” but she’ll know. By then, she’s probably put together what’s going on, and the shock she’ll feel is not the kind you want. 

This will be an awkward and uncomfortable shock, not the surprised and excited kind you’re looking for. 

Basically what I’m saying is don’t try and pull this off by yourself. Trying to pull off bringing your partner to her own proposal is one of the biggest proposal mistakes our clients say they regret after it happens. 

I would highly recommend creating a cover-up to avoid this. A cover-up is when you create an event or excuse that hides the real meaning of what you’re doing. It’s to hide the scent of the proposal so we can get that surprised and authentic reaction. 

We’ve helped execute so many cover-ups and we’ve had everyone from friends, family, and even bosses, help with planning. It’s a great way to involve people while you get time to prepare. 

proposal graphic with photos

Underestimating the Importance of the Cover-Up

Not fully utilizing, or not fully committing is the number one proposal mistake that we see when planning. To put it in perspective, we are one of the only proposal planners that really dive into the nitty-gritty of the cover-up because we believe it’s just as important as the proposal itself. 

Like I said earlier, women have a sixth sense when it comes to big events like this. 

It’s kind of freaky how we know when something’s off. By creating a cover-up, it not only gives you time to plan but throws her off the scent for what’s to come. 

The cover-up needs to be as much a part of the planning as the actual proposal. You need the timeline, who’s going to help execute, and the locations of where everything will be happening. 

The cover-up is a crucial step and it needs to be done right. Otherwise, you might as well invite her to her own proposal.

Make it Feel Natural

Women will see through it if the cover-up isn’t natural. One of the biggest mistakes we see when planning the cover-up is men not including parts of their girlfriend’s everyday life. It needs to feel like any other day, filled with things that she would potentially do.

By doing this, you ensure that she doesn’t suspect a thing. Also, make yourself unavailable. Say you’re out of town, or you’re busy that day. That way, she doesn’t rely on you for anything and you can take your time making the proposal the best it can be. 

Finally, only enlist the help of people who can take the pressure. Not everyone is capable of this level of deception. You need people who are able to stick to the plan so that the illusion isn’t broken. 

Overcrowding the Peanut Gallery

I would say, as a general rule of thumb, proposals are intimate moments between two people who have decided to spend the rest of their lives together.

It rarely happens with an audience, but I will say it does happen. The main downside to having an audience at a proposal is the number of variables that could go wrong. With each person involved, there are chances of them being late, or them not acting accordingly during the proposal. 

Not to mention that inviting a bunch of people to watch a private moment adds an unnecessary amount of pressure to both parties involved and often makes her feel uncomfortable. 

We’ve had to take women aside just to give them that space to become less overwhelmed. It’s a happy moment, but it can get away from you if you have a group of people trying to ask questions all at once. 

Not to mention, It creates a bigger opportunity for proposal fog.

man and woman hugging after proposal
Photo by: Golden Hours

Throw a Proposal After Party Instead

An alternative to this proposal mistake is to have a proposal after party instead. In case you aren’t aware, a proposal after party is a party at a location separate from the proposal site. The newly engaged will head over after they’re done to see friends and family who want to celebrate the big news. 

I will say that It’s the surprise that keeps on giving. First, your fiancee is surprised by the proposal. Then, she gets to be surprised all over again at the sight of friends and family waiting to celebrate your big night. 

The one downside to a proposal after party is the number of people who know the secret. 

Because this is an after party people are going to know that you are proposing. It’s imperative that you only invite people you trust, so as to not have loose lips spoil the surprise. 

Not Dressing to the Occasion

This is not a huge proposal mistake. However, for your sake, you need to make sure that your partner’s look matches the aesthetic of the proposal.  

What do I mean by “matches the aesthetic”? Well, she shouldn’t be overdressed or underdressed for the location.  

If you’re planning on proposing in a fancy hotel, don’t have her dressed in jeans and boots. Likewise, if you’re proposing outside in the park, a full-length ball gown isn’t the way to go. This prevents her from being embarrassed and is more focused on the fact that you’re asking her to spend the rest of your life together. 

If you’re not going to be with her when she’s getting ready, it’s important to talk with the people helping with your cover-up. They’ll know how she’s supposed to dress and make sure she’s dressed to the nines. 

Utilize a Stylist

It’s also important that you dress for the occasion as well. There’s a bit of a stereotype that men are not the best at picking out the right outfits. I hate to admit it, but there is some truth to it. 

You might think that what you picked out is nice and appropriate. However, it could be entirely wrong for the occasion. 

If I were you, I would take the guesswork out of picking the right thing to wear and hire a stylist. Whether you hire a personal stylist or use one of those “trunk” services, let the professionals choose the best pieces for you, so that you walk into your proposal in style. 

clickable proposal mistake graphic

Getting Her Nails “Proposal Ready”

Now you might be thinking, “isn’t having her nails done the one thing that all women want for a proposal?” Yes, it is. It’s also the number one giveaway.

For most women they get their nails done at least every other week if not weekly. If that’s the case, skip this section because it should be fairly easy to ensure that she’ll have her nails the way she wants for the proposal.

If that isn’t the case, you or a friend insisting that she go to the salon is a major flag. Especially if she’s the type of person who likes her nails to be more natural, or even likes to do them herself. 

Well, we found the perfect solution. In the past, we had a client who brought his partner’s favorite shade of nail polish to the proposal. That way, after he proposed, she could do her nails for the photos. It’s a genius win-win: she can her nails done, and the secret is safe. 

Not Hiring a Proposal Planner

This is one of the mistakes that we can totally understand how you would think you can do it on your own. You may have the ideas and even a location. What you may not understand is that having someone to do this for you so you don’t have to eliminates so many of the top proposal mistakes.

Such as trying to get your girlfriend to the proposal and she just isn’t feeling it.

Women get into these moods where we don’t want to see anyone or go anywhere (you’ve probably seen those moods). If you’re trying to get your partner out the door for your proposal and she is flat out refusing to leave the house, that causes you issues on top of trying to keep a schedule.

Or we have seen other situations where our clients have relied on friends to do the work. I hate to say it but they aren’t professionals. They mean well and have the absolute best of intentions but they don’t do this all day every day.

Putting Out Fires So You Don’t Have Too

There are going to be things that are missed and fires day of that need to be put out and you don’t get a redo.

I could write an entire blog post on “the fires we put out” and we are planners, it’s inevitable that something will not go according to plan such as weather. We are constantly looking at the weather and when you look down to see there are 40 miles an hour gusts of wind on a rooftop proposal that is not a scenario you want to find yourself in trying to pivot and adjust to pull off your dream proposal on your own.

Most of the venues that we work with are absolutely fabulous but it is not their job to run your event.

They aren’t there to tackle your weather issues. You hired the venue to provide the space you are renting, not to help you keep calm as the weather dampens your plans.

A professional proposal planner should help you avoid all the potential disasters and that is half the reason to hire a professional.

Overlooking Professional Advice

The last proposal mistake you could make is not listening to us– the professionals.

We’ve been doing this for over 12 years, we have seen it all and truly just want to give you the top things to think about so that you don’t find yourself in a place where your proposal ends in a reschedule, or worst things fall apart right in front of you.

However, this is your proposal. Take what you like and leave what you don’t in order to make your proposal what you want. If you want to ensure that you don’t make any of these mistakes during your planning, contact us to create your proposal and make it the best it can be for you and your partner.

About Jenée Strickland

Visions Event Studio specializes in luxury events, including proposals and couture weddings. Jenée Strickland, owner, and lead visionnaire, has been an integral part of hundreds of weddings and proposals. Her job is a privilege; her work is a passion.

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