Getting engaged? 3 Simple Steps to pull off a Magical Proposal

Getting engaged is one of the most significant moments in a couple’s life together, but planning a proposal can be stressful and confusing. Follow these simple tips to knock your proposal out of the park. 


I don’t envy anyone who has to plan, and pull off, an unforgettable, romantic, perfect (and all the extra descriptors) proposal. The stress that comes along with planning the proposal is only coupled by the fact that oftentimes, he is figuring it out ALL ALONE. 

For you fiances-to-be, I feel for you, so I thought it was about time a blog focused on the START of the engagement, the proposal. 

1. Plan the proposal around your partner’s personality

Whether or not your partner is shy or outgoing, if she values friends and family, find a nice compromise to include them in the proposal. Maybe they can be quiet spectators ready to cheer after the big moment is done, or maybe they can actually help you pull off the surprise. 

But if she wants them there, you make it happen even if you are a little shy yourself. 

You know your partner best, so when you are planning the proposal, think about what she values the most in her life and also consider her personality as you’re making plans. 

Is your partner shy or outgoing? Is your partner very family-oriented or does she prefer to be with friends? Is a certain person or animal an important part of your lives?

Think about these questions and more before finalizing your plans.

If your partner is on the more private side and would be absolutely mortified if you propose in front of a large group of people, I definitely recommend a low-key, personal, private proposal.

One way to provide an intimate experience is through the location choice. A weekend getaway to a small vineyard, an overnight in a nearby city, a beautiful local park, or the place you met are great options for a private engagement location.

On the other hand, if your partner is very outgoing and loves a big surprise, use that to your advantage, and plan an engagement that will fulfill her love of socializing by including friends and family in some way. 

2. Opt for the surprise 

Attempting to truly surprise someone, and I mean actually surprising them in the “seriously had no idea type of surprise” is very difficult. To pull that off with a proposal means you’d have to choose a ring yourself without any partner input, plan the entire proposal without telling anyone, and pull it all off with no help. 

There’s a saying, “You tell one person, you’ve told the world” or is it “the walls have ears”? 

Actually, it’s both. 

But here’s the thing, telling NO ONE is nearly impossible for various reasons, so rather than telling absolutely no one if that’s not possible, just tell your “ride or die” because you know that person is the end of the road as far as secrets are concerned. 

And don't worry, pulling off a surprise engagement is about more than just your partner truly having no idea it’s coming. 

So how else can you surprise your future fiancé during your engagement?

Choose an obscure date to propose

I’m not sure if you know this but the weeks and months from Thanksgiving to Valentine’s Day are known as engagement season in the world of wedding planners. That basically means that everyone expects you to get engaged on, or around, these holidays. 

But if you’re looking to pull off a serious surprise that no one expects, try choosing a different time of year, an obscure date, or a random time of day to really throw off your partner. 

Hire a photographer to capture the moment

A more recent trend in engagements is hiring a photographer to idle nearby the proposal site in order to capture the big moment without tipping off your partner. Photographers have gotten pretty good at pulling the incognito photoshoot off, and don’t worry, he/she won’t tell anyone about your secret. 

This might seem unnecessary to some people, but I assure you that these photos will become treasured memories one day especially for those people who are not there to witness it in person.

Throw a surprise Engagement Party

A big engagement party or a small dinner, something to celebrate being engaged is such a nice way to follow up such a big moment in your relationship. It doesn’t have to be huge if that’s not your style as a couple, but even a surprise intimate dinner following the proposal would be a great way to celebrate your engagement. 

But Janet, you just told “the walls have ears”. Yes, I know.

So my advice to keep the actual engagement a secret until the very last minute is to LIE.

It sounds a lot worse than it is. You can plan a disguised party so that guests believe they are attending something completely different. 

There are so many options for fake parties: birthday (for whoever), holiday gathering, I mean honestly it could be a superbowl party. Anything to get people in the same location so you can surprise them with the true reason for the celebration. 

Does planning all of this make your headspin? Guess what? I don’t just plan weddings. I can help you plan an engagement party as well!

PRO TIP: If you plan to tell guests that this is an engagement party, and you have a person who isn’t great at keeping secrets, tell that person’s significant other to invite him/her to a fake event so they don’t book anything else that day. The significant other can tell the “not-so-great-secret-keeper” the real event once they are on their way and it’s too late to blow the surprise. 

3. Consider Traditional Elements 

While some couple’s today are more modern, I do think there is something to be said about a traditionally structured proposal. Your significant other may have been imagining a proposal since she was playing with barbies in the 1st grade, so if that’s the case, tradition will be your friend. 

What do I mean by tradition? 

Speak with her parents

Although the true tradition is to ask her father for her hand in marriage, a more modern approach is to speak with both of her parents about proposing. 

Ok listen, before you go all Karen on me, hear me out.

You know your significant other. You know the family dynamics. If she hasn’t spoken to her parents in years, this advice isn’t for you (but check out my other blogs for great wedding planning tips!) 

There is something to be said about some traditional values though. Does this mean I want you to collect a dowry in exchange for a wife? No. 

But, there are some people who value family involvement, and the idea of an old-school engagement, which starts with a conversation with her parents. 

In general, it’s not so much that you're asking for their permission to marry her. It’s more so a conversation so that you can tell the parents that you plan to propose, maybe share some details of the proposal, and if you’re brave enough, tell them why you want to marry her, and your hopeful plans for the future. 

I can assure you of one thing. If your partner has traditional parents, they will appreciate this conversation more than you realize, and at the bare minimum, it will start your relationship with your future in-laws off on the right foot. 

Get down on one knee

Does your future fiancé watch romantic movies or TV shows? If so, I can promise you she expects you to get down on one knee when you propose. 

Yes, this is traditional, but *swoon* what an amazingly sweet, beautiful moment in your journey, and *double swoon* what an epic photo op it provides. 

PRO TIP: When you get down on one knee, please please please don’t sit back on your heel. Hard truth…it looks terrible, and if you spent money on a photographer you will thank me for this advice. 


In the end, remember that your proposal is about you and your future spouse. You are making a huge gesture to show your partner that you want to spend THE REST OF YOU LIFE with her. 

That’s a big moment in time. So give it some thought, take time to plan something special, and make it a day you’ll both always remember.



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