Home Groom Life Groom Life: Things To Think About Before Popping The Question (And A Few After)

Groom Life: Things To Think About Before Popping The Question (And A Few After)

written by Jon Huston August 29, 2018

We’ve outlined the who, what, when, where, and why of getting engaged, with a little bit of how to plan thrown in!

In 2014, I was lucky enough to marry the love of my life. We had been together for three years prior to our wedding day, traveling together throughout South America and all over the United States, having shared a tent on countless backpacking trips and a scenic perch on many mountaintops. As we collected amazing experiences together, it became clear to me that I wanted to spend the rest of my life with her. It just seemed like an easy decision.

When it came time to propose, I dreamed up what I expected would be the perfect proposal. We climbed to a high alpine lake overlooking a little mountain town. It was the 4th of July and I planned to propose as we watched the fireworks burst over town in the distance. After all my planning, I was still a nervous wreck! I wasn’t calmed when the fireworks I’d imagined to be gigantic and loud actually appeared as tiny specs in the distance with no sound at all. We chuckled and drank wine as I nervously wondered when the ‘right time’ would be. Soon, it seemed that the distant specs were culminating in a miniature finale so I nervously dropped to my knee, kicking over her wine in the process and dropping the ring on the ground. As I awkwardly recovered the fumble and sheepishly asked her to marry me, she smiled with tears in her eyes and said “Yes, of course! I wondered why you’d been acting so weird!!”

While it was an incredible moment we will never forget, I can assure you that it was filled with far more detail and nerves than I ever thought possible – and I still overlooked so much. Here are a few things I learned and a few suggestions to consider for any future fiance or groom-to-be. Maybe you can be a bit more prepared and a little less nervous than I was.

The 5 W’s & 1 H of Marriage Proposal…


The Who of your plans relate to who you need to plan, communicate, and coordinate with. Most importantly, there are many traditions related to wedding planning so it’s important to ensure that you are notifying and gathering permission from all the proper parties in advance of planning your proposal. Be respectful of parents, friends, and loved ones and be sure to include those that are important to you. You don’t want to start this positive experience with hurt feelings or frustrated parties. Be sure to include all the important family and friends, but be sure not to blow your surprise.


The What of your planning comes down to what you will do to pop the question, followed by what you will do to commemorate, celebrate, and communicate. Remember to have a camera ready for some great and emotional photographs. Also, ensure that you have all the supplies and assistance necessary to pull off any special planning. Originality and personality are key to a great wedding proposal so be thoughtful of your relationship and your partner, and do your best to create a special storybook experience that will be remembered – and shared – for a lifetime. Unless your a professional actor, the nerves of the moment will likely leave you stumbling and speechless. That’s okay! It can even be cute. A bit of forethought can help, but don’t stress. Simply speaking from the heart is the only true way to make your proposal as epic as it should be. You’re going to nail it!

What Will You Do To Help With Wedding Planning?


You’ve heard that timing is everything – and that is a key factor in determining the When of your wedding proposal plan. When you ask may be determined by when you expect to hold your ceremony or when you expect your guests to be available. Beyond that, you’ll need to determine when the right time to share the news with everyone is, in addition to when to begin your planning, purchasing, reserving, and so on. If you want to be married in a popular venue or in coordination with a specific date or holiday, it’s probably best to plan as early as you can. This will make your planning feel more organized and less rushed.


The question of Where relates to where you will propose, as well as where you will seek to be married. Like I stated above, the location of your wedding venue may have great bearing on when your wedding can be held. Another factor to consider is any travel your guests may need to invest in to come to your event. Will it take them hours, days, more? Will they need to save money for tickets or reservations? Will you? While the answer to where you will be married may seem simple to begin with, the logistics of managing the event and coordinating all the needed services and reservations can be more complicated than you think. Consider this in advance.

What Can You Do To Help Out On Your Wedding Day?


So, why deal with all the stress and strain of planning a wedding? Hopefully, it’s true love! Other great reasons include the amazing fun you’ll have celebrating with friends and family, some of whom you may never see again or share time with in the same way. Another fantastic reason is the fact that your wedding day is a rare and unique opportunity to splurge on yourself and make everything about your big day. You’re spending the money, so you get to pick all the delicious food and drinks, as well as all the guests, you want!


A few additional things to think about in advance of proposing marriage…

How much will you spend on an Engagement Ring? Wedding Ring? The prices range tremendously in this arena so it’s important to set an affordable budget for yourself. Contemporary brides are also changing their tastes for diamonds and other stones, as well as the ring styles themselves, so it’s probably a good idea to attempt a conversation about this in advance. If you trust your judgment and know her tastes – go for it! Otherwise, covertly consult with her or a trusted friend or family member.

*If you’re not really a jewelry person, it’s important to keep in mind that it will be a new thing to have to worry about losing, scratching, and caring for an expensive ring. It may not even fit properly! Have a safe place to store or wear it until it can be properly sized and cared for. (We had quite a hike home when we learned the ring didn’t properly fit my wife’s finger but found that she didn’t want it to leave her sight!)

How much will you budget for the Wedding? How long will it take to save? Depending on your financial circumstances and the vision you have for your big day, the costs can vary greatly. We recommend at least developing a ballpark for what you expect to spend and take some time to determine how long you’ll need to save. This will help your planning and timeline in a big way – and may have a dramatic impact on your desired wedding date.

How can I save money, but not look cheap? There are many ways to save money in the planning and decor of your wedding ceremony – like DIY projects and smart decorative choices. I wish I would’ve been more aware of companies like FiftyFlowers.com at the time we were married. It’s a great resource for looking at trends and colors, and we could’ve saved a ton on flowers! It’s important to do your research and be aware of both, your priorities and your creative abilities. We’ll cover some more ways to save and be creative in future articles.

Are There DIY Wedding Projects To Help Save You Money?

While there may be a lot to consider before (and after) asking someone to marry you, if it’s a good match and you’re happy together, it will be well worth it in the end. You’ll have a wonderful opportunity to create lifelong memories with family and friends – and you’ll get to share the experience together! All the stresses and struggles of picking and choosing and planning and dreaming will come out exactly as they’re supposed to. And even though each wedding seems to experience its own ‘flops’ and ‘frustrations’, those will likely be some of the things you reflect most fondly upon as you gracefully manage them together and still have the time of your life. Cheers to you! It’s hard to imagine it all before you even pop the question.

Stay tuned for our next edition of the Groom Life Series…

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