Our Engagement Story: A Personal Tale of Love and FIRE

Join us as we share our engagement story, blending our love for each other with our path to financial independence, retire early (FIRE).

Launching our blog amidst the pandemic’s bloom, we aimed to offer a fresh perspective to the FIRE community. And our engagement story is as personal as it gets, reflecting our journey and personal values.

We’re excited to peel back the curtain and share this deeply personal chapter. From the meticulous planning and heartfelt decisions that shaped this moment—to our entire budget for the proposal—we’re opening up about it all. We hope that by sharing these details, we can offer valuable insights and inspiration to others navigating similar financial and life paths.

Our Engagement: A Fusion of Love and Dollar Wisdom

In the first post of this marriage series, we discussed the practical benefits of marriage from a detached perspective—focusing on the legal and tangible changes to our relationship.

Today, let’s look at our personal experience of making a momentous, life-changing decision. Commitment to marriage.

Couples embark on their engagement journeys in many ways, each unique and memorable:

  • Some drop to one knee in front of iconic landmarks like the Eiffel Tower.
  • Others opt for a surprise during a family gathering.
  • Then some choose the comfort and intimacy of home.

The spectrum of proposals ranges from movie-like extravagance to the quiet peacefulness of familiarity.

Just like with FIRE, the goal isn’t to do nothing (spend nothing), but rather it’s to maximize the value of the effort (money) that goes into the event.

Remember, this is your engagement. And eventually, your marriage. Don’t let other people’s experiences and judgments define what is right for you. I’m only here to offer you our experience and show you how it might differ from the norm. Make your engagement personal, don’t let comparison be the thief of joy in this moment of your life.

I wanted to show Jenni how much I care—and that’ll require much more than a blank check.

Proposal Vision: Blending Sentiment with Strategy

When I decided to propose to Jenni, I aimed to blend various elements of our journey together:

  • Remind her of our history of growing up together.
  • Involve close friends, family, and our community.
  • Add surprises and a sense of adventure into the mix.
  • Express my emotions by showing effort, intention, and deep desire.

It’s worth noting what you won’t find on this list: extravagant meals or a lux trip to Disney.

Not that I wouldn’t happily book a cozy table at a local place and ask her there. And it’s not that I’m unwilling to jump on NetJets and whisk her off to a secluded island where I’ve hidden a ring under a shell for her to find.

I mean hell, we’ve certainly got the money.

Rather, it’s about aligning my proposal with what I know she values and creating a reflection of what I envision for our relationship.

There wasn’t even a diamond in sight! Let’s get to that…

Ring Shopping: Is It Really Needed?

As soon as I decided to propose, my mind began to race with visions of how and where to do it. While dreaming up the perfect scenario was fun, the practical side of me knew I had to tackle the ring question—whether to have one and what type it should be.

Knowing both Jenni and myself well, it became clear that a standard engagement ring from a jeweler wasn’t going to work.

Jenni values sentimentality—a family heirloom or a custom piece would speak volumes more than something mass-produced—no matter how big the glitzy rock in the middle was.

Is an engagement ring appropriate for us?

Some traditions are enjoyable and still feel appropriate, but others feel antiquated. Relics from a time of a wider discrepancy in rights between genders. Where did engagement rings fit into this spectrum?

Historically, Jenni has worn rings—so that part wasn’t an issue. And she does own some diamond jewelry—some of which I purchased!

So, the idea of a ring itself wasn’t the issue.

What gave me pause was the symbolism. Was it a token of ownership, or could it reveal something more profound and personal?

I went back and forth on this but decided Jenni would appreciate the sentiment behind it more than any potential negative symbolism—as long as I personalized it.

So, ring it is.

What kind of engagement ring would my partner love?

Since neither of us had an heirloom to use, the best option I could see was to have something custom-made or hunt down a beautifully crafted ring from the past.

I spent a while perusing local estate sales and online listings for historically significant rings. Jenni has always loved jewelry with Celtic Knot designs—twisting, turning, and multiple circular elements. Naturally, I looked at several Celtic engagement rings and wedding bands.

Rare, cultural rings—gimmal rings

While digging through those options, I ran into something unfamiliar: Gimmal rings.

A Gimmal ring at the Met Museum from roughly the 15th century.
A Gimmal ring at the Met Museum from roughly the 15th century.

This union of rings was historically popular as engagement rings because they could be separated. In a two-hoop ring, each partner could hold a ring until the wedding. In a three-hoop ring, a third person, serving as a witness, could hold the third piece until the wedding day.

I thought this was a lovely idea! I started exploring modern Gimmal rings.

They exist, and in fact, the metal-smiths of Colonial Williamsburg (not far from us!) produce them in a historic style with two hands clasping each other.

Unfortunately, these tend to be fused. I liked the idea of a ring that came apart and moved.

Inspiration for personal engagement rings

I drew inspiration from a ring Jenni has worn on her thumb since we were just kids.

The little three band silver ring on Jenni's thumb since she was a teenager—my inspiration!
The little three-band silver ring on Jenni’s thumb since she was a teenager—my inspiration!

It’s a three-hoop ring that doesn’t come apart but has bands that roll over each other. I remember fidgeting with this ring on her thumb frequently when holding her hand as a kid.

A multi-piece, personalized ring—the puzzle ring

Continuing my hunt, I learned about puzzle rings, popular in England during the late 19th century. They come in various band counts, mostly four, and artisans assemble them in a specific order—forming a puzzle. Generally, they don’t come fully apart. They’ve recently seen a resurgence as wedding bands.

A classic, simple puzzle ring that's been made for centuries.
A classic, simple puzzle ring that’s been made for centuries.

This was an appealing idea to me. It hit several points:

  • Atypical, yet can still pass visually as a traditional marriage sign
  • Something more “functional”—a little puzzle for Jenni to play with that’s always there
  • Can be customized

For customization, I found a jeweler in Tennessee who still handcrafts each piece—and has done so for nearly 70 years.

At that point, I was sold.

Customizing the puzzle ring for a proposal

I went back and forth with the jeweler, brainstorming ideas for customizing an engagement ring to fit Jenni’s interests. Which metal would be best? Maybe even a mix for each band? Plus, I could pick from a variety of stones.

I settled on either white gold or silver, as Jenni doesn’t tend to wear yellow gold. Platinum was an option, but given our tendency to lose things, it didn’t make sense to invest heavily in a single small object.

Considering Jenni’s activities—kayaking, rock climbing, and gym workouts—I knew she’d heavily wear a ring and possibly lose it. I wanted to get wedding bands from the same jeweler, so I had to consider my tendency to lose and damage things, too.

Following the prep and planning rule that “two is one and one is none,” I intended to order a duplicate of the engagement ring. I’d let Jenni weigh in on doing the same for our wedding bands in the future.

Ultimately, it made sense to go ahead with a silver ring and a gemstone that matched her favorite color—green. I selected a rainforest topaz.

The engagement ring on Jenni's finger. :-)
The engagement ring on Jenni’s finger. 🙂

After the proposal, ensuring the ring was the right fit (update: it wasn’t!), I’d have Jenni pick the metal for the planned duplicate, too.

With the engagement ring settled, I moved on to the bigger picture—the proposal event.

Our Engagement: The Theme and Purpose

With the engagement ring ordered, I had time to focus on the proposal itself. While browsing the multi-band puzzle rings, an idea struck me. Jenni’s engagement ring comprised four bands, and I saw them as a metaphorical engraving.

What could these four bands represent?

I reflected on what’s important to us—in life and our relationship.

We care deeply about our relationships, investing lots of energy, time, and effort into supporting those around us. That energy comes back to us multifold, but it’s central to our lives.

We love traveling with our close friends and adventuring through life.

Our family and friends are always there to support us—and we, them.

Combined with our neighbors, acquaintances, colleagues, gym buddies, co-volunteers, and others—you get our community.

Through this wide-ranging group of people, we share our love.

That’s the essence of our marriage and wedding. A sign to our community that we’re dedicated to each other and them.

This idea became the theme of our proposal, involving everyone important to us.

Friends, Family, Community, and Love. Our four circles.

The theme of our engagement—friends, family, and community coming together to celebrate love.
The theme of our engagement—friends, family, and community coming together to celebrate love.

Our Engagement: The Proposal

With the ring on order and a theme set, I began working on a plan for the proposal. I wanted to involve our dearest friends, family, and community. But without turning it into a big public spectacle.

This would be no Disney World show.

I considered a million possibilities. We’ve been together so long that it’s hard to “wow” Jenni. I’ve surprised her with flights to Caribbean islands, whisked her off on romantic European tours, and much more.

Making a Proposal Meaningful

Reflecting on it, I realized what would truly surprise and touch Jenni was involving our history in a deep and meaningful way—not all at once, but gradually.

So, the idea of a scavenger hunt started to come together.

But, she wouldn’t be searching for things—it’d be people. People from our past and our life together.

I began recruiting people with ideas for where Jenni might meet them in a scavenger hunt across our home state of Virginia.

Proposal Planning: The Scavenger Hunt

I’d kick things off with a small clue one morning and a planned innocuous road trip.

We met in middle school, so it seemed fitting for our first stop—along with some of our oldest friends from that time.

Our first date was at an ice skating rink, where our dads drove us. So, guess who the clue from the previous stop would lead to…?

Crisscrossing the state, heading back south, we’d stop at an old train station—a route we used to frequent to see each other after college—where Jenni’s pharmacy preceptor would be waiting.

Getting closer to home, we’d have a quick rock climbing challenge given by local friends and fellow climbers.

An example of a "clue package" I gave each person helping with the scavenger hunt. Each with a unique clue and hidden message to be used later.
An example of a “clue package” I gave each person helping with the scavenger hunt. Each with a unique clue and hidden message to be used later.

I think you get the idea. I’ll summarize the next several stops, all near our home. We’ve lived in many places together, but none more meaningful than the first—so it made sense to stop by our old place, with family ready to offer a clue out front. Plus, we had to stop by our current place—more family—and then off to some of our favorite local haunts: parks, trails, and friends.

Finally, we came to the last stretch of the trail along a riverside, right at a bench we frequented as our turnaround point on long trail runs together.

Popping the question

Just like any other time, it was the perfect place to sit and rest.

Watch the sunset over the water.

And recover a little.

I recorded this brief timelapse in 2015 (!!) from the perspective of sitting on the bench.

But then, I told Jenni to pull out part of the first clue I’d given her 48 hours prior. A sealed envelope with a little note inside.

She opened it and read:

“Look up!”

After she glanced at the sky, she realized I was down on one knee in front of the bench with a hand-carved little wooden box.

And something inside it.

She said yes!

But just as I was putting the ring on her finger, it came apart into the four loose bands.

…We weren’t done yet!

Post-proposal Celebration

We jogged off down the remains of the trail where a sneaky friend had hidden a car for me. One stop left.

A short drive, a curious Jenni, and an anxious me.

We pulled into an unknown driveway, walked inside… and: surprise!

The 16 people who had given us clues throughout the day were waiting to help with the final step—putting the puzzle ring together!

Each person unknowingly kept a clue that was a step in reassembling the ring.

I literally couldn’t get engaged without them!

With their assistance—and a few laughs as we fumbled with the ring—I had the chance to reenact the one-kneed proposal ring placement. Pictures, congratulations, and cheers followed.

A reenactment for the engagement party attendees. On one knee and a yes!
A reenactment for the engagement party attendees. On one knee and a yes!

We were engaged!

But that’s not quite all!

Our friends and family stayed because I’d also planned entertainment and tasty eats for everyone that evening. The house we were in was a large Airbnb with a pool and hot tub for everyone’s use.

I hired a private chef to cook an expansive and allergy-friendly meal for everyone present.

Jenni and I had time to relax, tell our tales from the past two days, and celebrate with those closest to us.

And that’s how these two FIREes got engaged!

Proposal & Engagement Cost

But, at its core, this is a personal finance blog, so let’s talk numbers. What did this all cost?

You might recall a mysterious “gift” line in our August budget last year—that covered most of our engagement-related expenses.

Let’s dig into the numbers:

DescriptionCost ($, USD)Comments
Carved, inlaid ring box37.05Handmade, customized.
Jeweler 2x engagement,
2x wedding rings (4 total)
388.00Handmade, customized.
Papersource Store27.56For handwritten clues and notes.
Ice skating in NoVA48.004x people—couldn’t miss this!
Lunch in NoVA82.10Took friends out that helped.
Dinner in Washington, D.C.93.11Night before proposal day.
Overnight parking in D.C.13.72Parking for free (points) hotel stay.
Ring Size Adjuster6.36Temporary solution, too loose!
Private Chef1,769.5320 servings.
Airbnb Celebration410.40For engagement party, chef.
Total2,875.83

So, just under three grand. Surprisingly, we spent the bulk of our budget on the celebration we had after the proposal. The engagement ring and box themselves were relatively inexpensive.

This figure varies slightly from our previous post, as it now includes some related expenses categorized differently, excludes discounts like those applied to Airbnb, and factors in costs spread over different months.

Our hotel stay in D.C. was effectively “free” by using Hyatt points, valued at about $250. Additionally, there were no listed gas expenses for all the driving, which might have totaled around $30. We also provided beverages—beer, cider, wine, and cocktails—for the Airbnb celebration, valued at about $200, most of which we already had at home.

All considered, the actual total cost likely approached $3,500.

An Engagement Conclusion

Reflecting on our engagement story, I believe there’s an important lesson to be learned. We infused every decision—from selecting a custom and personalized ring to planning a deeply meaningful proposal—with our shared values and personal preferences.

It wasn’t just about the moment of the proposal—or some big performance.

Rather, it was about highlighting what we’ve already established as important and letting that shape our future together.

For some couples, it will seem like we spent far too much on a single party. For others, it’ll seem like we cheaped out on the ring (Ramit has plenty to say about this). But it’s what works for us, and focuses on what we find important.

I’d like to think I’ve gained a little wisdom from this experience. I’ll offer you some tips if you’re on the path to FIRE and considering getting engaged:

  • Personalization is key: Tailor your approach to reflect what truly matters to both of you. Whether it’s a unique ring design or a meaningful proposal environment—maybe even a wild 36-hour scavenger hunt—personal touches make the experience leave a mark on you both.
  • Balance emotion with practicality: Getting that big “wow” when you reveal your plan is great, but remember, this marks the start—or at least a new chapter!—in your life together. Consider factors like practicality, durability, and what’s important to you as a couple beyond that immediate wow factor.
  • Plan, plan, plan!: If you want to surprise your partner, show that you’ve been carefully working to express your love. Details matter. You don’t need grand gestures, you need thought and caring. And remember, two is one and one is none.

We’re both very excited to continue to share our engagement story as it transitions into our wedding story. Keep an eye out for our third post in this series about our wedding plan. Not long after, we’ll have a detailed breakdown of our wedding expenses.

Share your thoughts below and join us as we continue to intertwine love with financial independence.

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By Chris

Chris began his financial independence pursuit in 2007 as he learned basic personal finance from Get Rich Slowly as an aspiring web designer and novice investor. After several missteps, he learned the secrets of financial independence and began his pursuit of freedom.

He reached financial independence in 2018 with $1.2M and two businesses. He began the process of transitioning to early retirement in 2020.

Learn more: Meet Chris.

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