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Planning the Proposal: Tips from a Guy who Just Proposed

So, you’re ready to propose. Do you even know where to start or what to do? Don’t worry, you’re not alone - I had no idea either. I asked a lot of people a whole lot of questions as I tried to navigate this process and learned a ton along the way. For those of you who are in a similar boat and aren’t sure what to do next, I will walk you through the process and share advice that was given to me, 

This is a massive step! It is incredibly nerve-racking because you are now beginning to see your future with someone else in it. I know that, for me, it was (and is) a big change. I'm very independent and I enjoy having that freedom. That will change; you now have another person whose feelings and wellbeing you must take into consideration when making decisions. And these decisions no longer just affect you. I could spend all day telling you how I almost got cold feet when proposing; but now, having gone through it, I can honestly say it was the best decision I’ve made, and hopefully I can help you on your way.

So, where to begin?

The decision to propose is yours and yours alone

I would say, first and foremost, make sure you are in love with this person and you are proposing because you want to. Not because people think you should or because it has been so many years or even because your significant other is pressuring you. If you only take one thing away from this blog post, let it be that this is your decision and nobody but you can make it.

Talk to the parents

I’m on the old school side of things when it comes to asking the parents for permission. I think this is incredibly important, because you aren't just marrying your significant other, you are also marrying into their family. This, to me, is a huge sign of respect to the parents and I think goes a long way in building a great foundation for the future. Keep in mind there may be other questions but be prepared to answer questions like:

Are you ready for this kind of commitment and why do you think you're ready?

Why do you want to marry my daughter? What qualities do you see in her that make you want to marry her?

How do you plan on supporting my daughter financially?

You will argue and fight; how will you manage and resolve those conflicts?

Why do you think you deserve to marry my daughter?

These are important questions that every parent wants to know the answer to before they give you their blessing. This part of the process can be tough, but it is well worth it!

Finding and picking the ring

By now, you should have a decent idea as to what style of ring your significant other wants. If you don't, you haven’t been paying close enough attention. IF, for some reason, you are still unsure of what she might like, talk to her close friends - just make sure they can keep a secret! I actually went to look at rings multiple times with my fiancé long before I was ready to propose, just so I could have a better idea of what she liked and wouldn't have to risk spoiling the surprise. Picking out the perfect engagement ring comes with a whole lot of options, ranging from the shape and size of the diamond to the type of precious metal to the thickness of the band. (For everything you need to know about how to pick an engagement ring, click here

Insure the ring!

Whether you have worked with a jeweler to custom design a ring, or you have purchased one ready-made, the most important thing you can do at this point is insure the ring. I cannot stress this enough: get the ring INSURED! Engagement rings are expensive, and the last thing you want to do is pay for a ring and then have something happen to it. We’ve all seen those heart-stopping videos where the guy drops and loses the ring mid-proposal. By insuring the ring immediately after purchasing it, you will give yourself peace of mind. 

The moment I got the ring, I went online to and had the ring insured within minutes. All you have to do is enter your personal information and upload documentation of either the receipt or the appraisal of the ring. Keep in mind, as with any insurance, the more expensive the item is that you are insuring, the more money you will be paying to insure it.  Jewelers Mutual makes it super simple and easy and they are dedicated solely to insuring jewelry. But shop around to find the best deal and what you are most comfortable with.

When, where, and how

This is where the fun begins. All the little things she has told you about herself, the things she loves, those side comments she thinks you aren’t paying attention to, they will all come into play at this moment. It’s like having a spare tire, you never need it until you actually need it. And, trust me, you now need every bit of that information. All of those little intricacies will help you determine the logistics of your proposal and make it truly special and unique to her. Does she want her family there? Does she want it to be close and intimate with just the two of you? Does she want to know it's coming so she can be prepared for it, or does she want to be completely surprised? Has she always dreamt of a certain location or about how she would be asked? Personally, I have always felt as though the process of the proposal is for us and the proposal itself is for her. Most girls dream about the day they get engaged, just like they dream about the day they get married. It's our job to make it as perfect and as memorable as possible for them. Listen to the details and try to incorporate them in any way you can.

Ask for help

Don't be afraid to ask for help. Just make certain that whoever you involve won't spill the beans! I asked my fiancé’s parents and grandparents for help throughout the entire process. It was even more fun because we all knew something she didn't, and let’s be honest, who doesn't like keeping a good secret? I would not have been able to pull off the proposal I did without the help of both of our families and friends. If you are a bit uncertain on some of the details, this is a great way to loop the parents into the proposal to get their ideas and feedback, while also making them feel like they are involved. This is the beginning to the rest of your lives together and what a better way to start it off than by making an unforgettable memory with both of your families. If you'd like to see our proposal video, check it out here.


Lastly, a very important component of pulling off an unforgettable proposal is making sure that it is documented. If it's in your budget, it is well worth it to hire a photographer and even a videographer if you'd like. For the video of our proposal, I simply used an iPhone and an iPad, strategically placed out of sight, to get two different angles. You also don’t need to hire a professional - you can always ask a friend or family member to photograph or record the proposal for you. However, there is something really nice about knowing you have a professional capturing that incredible moment. If you do manage to get the proposal on video, you can always get it edited by a professional, and it can be a special gift to give your bride on your wedding day.


At the end of the day, these things are all important and will help make this day extra special. But truthfully, there is nothing more special than asking the person you love to marry you and having them say yes. All the details make for a great story, but just remember, you are starting the journey of spending the rest of your life with the love of your life and nothing is better than that. 

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