Relationships

Should You Upgrade Your Engagement Ring? The Hosts of ‘Give It To Me Straight’ Weigh In

September 25, 2025

Women wearing engagement ring — Photo by Alekon pictures on Unsplash

When it comes to engagement rings, there’s a lot of cultural weight attached to that little band of metal and stone. But what happens when your life has changed since you first said “yes”?

On Give It To Me Straight, hosts Alex Madison and Jon Bouffard tackled a listener’s question about whether upgrading her original ring would be superficial—or simply a celebration of how far she and her husband have come. Their take? Less guilt, more sparkle.

‘I think it’d be fun’

When the listener admits she wanted to upgrade her engagement ring simply because “I think it’d be fun,” Alex and Jon immediately latch onto that motivation. They laugh at her honesty—not in judgment, but in appreciation for how refreshing it was. For them, that lighthearted reasoning was enough to justify the decision. After all, marriage is full of serious milestones and tough choices, so why not lean into joy when you can?

“It would be fun—for her,” Jon points out, explaining that it’s okay to embrace a little frivolity when it feels right. Sometimes, the best reason to do something in a marriage isn’t practicality or sentimentality—it’s just because it makes you happy.

Upgrades as symbols of growth

Alex and Jon see upgrading a ring as honoring how far you’ve come together. Jon believes that milestones in a marriage deserve to be celebrated in ways that feel meaningful, even if that means swapping out the original stone for something new. “Even for the husband, I think it’s really cool to be able to do something like that for your wife because it’s an accomplishment,” he says. It’s about marking a shared journey: starting out with what you could afford, then years later choosing a piece that reflects your stability, your growth, and your story. The ring becomes proof that you’ve built something lasting together.

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Keep the original ring—and get creative with it

One of the listener’s biggest concerns was whether upgrading her diamond would erase the sentiment tied to her original ring. Alex shares her own experience to show that doesn’t have to be the case. “My original ring that you proposed to me is meaningful and I won’t sell that…but I do want to do something special with it and turn it into something different,” she explains.

For some couples, the first ring is a symbol of the early days—scrappy, hopeful, and rooted in love over luxury. Holding onto it means you still honor that chapter while giving yourself permission to evolve. Whether you transform it into a necklace, a right-hand ring, or even pass it down someday, there are countless ways to keep the memory alive without feeling stuck in it. An upgrade doesn’t have to replace your story—it can add another layer to it.

Sentimental vs. practical: not everyone sees it the same

Not every couple treats objects with the same weight, and Alex and Jon are upfront about that. For them, most things are replaceable. “The only things that matter are the people,” Alex says, listing off her family and pets as what she truly values. But she acknowledges that for many couples, the engagement ring holds irreplaceable meaning—it’s the piece that marks the beginning of a lifelong commitment. That’s why the question of upgrading a ring is so personal: one partner may see it as a fun way to celebrate growth, while the other might feel like it undermines the original symbolism. Neither perspective is wrong. It really comes down to knowing what matters most in your relationship.

At the end of the day, Alex and Jon say that you don’t have to choose between sentiment and sparkle: “Don’t replace it. Add to it.” That way, you honor the past while stepping into the future with something that feels just as special as the day you first said yes.