The Big Wedding Regrets: A Couple Spills the Tea on What They’d Do Differently

Getting married is one of life’s biggest milestones, but planning a wedding? That’s another story. While some couples look back on their big day with nothing but joy, others have a few “wish we hadn’t” moments. We sat down with a (fictional) couple, Emily and Jake, to talk about the things they’d do differently if they could turn back time.

Cakewalk: So, let’s start with the big question—what was the best part of your wedding?

Emily: The actual moment we got married. Standing there, holding hands, saying our vows—that was perfect. But everything leading up to that? A bit of a circus.

Jake: Agreed. The moment we exchanged vows was incredible, but we spent so much time stressing about the details that we barely enjoyed the journey.

What was the most stressful part of planning your wedding?

Emily: The guest list. We had over 150 people, and trying to balance expectations, plus dealing with family politics, was exhausting.

Jake: And the cost! Every time we turned around, there was another unexpected fee. We started with a ‘reasonable’ budget, but it kept growing. By the end, we had spent way more than we ever planned.

Looking back, what would you do differently?

Emily: Honestly? A smaller wedding. We got so wrapped up in what everyone else wanted that we forgot what we wanted. If we could do it over, we’d go for something intimate—maybe 20 people, max.

Jake: Or even an elopement! I used to think elopements were just Vegas chapels and Elvis impersonators, but now I see how elegant and meaningful a small wedding can be. We could have had a simple, beautiful ceremony in a spot we love, and saved ourselves a year of stress.

What’s one piece of advice you’d give to couples currently planning their wedding?

Emily: Don’t make decisions based on other people’s expectations. It’s your wedding, not a family reunion. If a smaller, more intentional celebration feels right to you, go for it.

Jake: And keep it simple. We thought we needed a huge venue, elaborate catering, and a packed dance floor. But the best part of the day was just us, promising forever. I wish we had made that the focus from the start.

Considering a Simpler, Stress-Free Wedding?

If Emily and Jake’s story resonates with you, there’s good news: you don’t have to go through the same regrets. Cakewalk specializes in beautiful, intimate weddings that let you skip the stress and focus on what truly matters—your love. Whether it’s a chic city elopement, a cozy gathering in a hidden garden, or a simple ceremony in a stunning public space, we make it easy.

Let’s make your wedding feel effortless. Contact us to start planning a celebration that’s meaningful, personal, and exactly what you want.