When should I get engaged?

Get Engaged Long Before You Start Planning a Wedding Here's something nobody tells you when you get engaged: wedding planning will suck the fun right out of the new excitement being engaged if you let it.

Logistics have a way of putting a damper on fantasy and fun and emotions. Planning is a lot of logistics and deciding what you can afford. I've been planning weddings in Aspen for over a decade, and one of the biggest regrets I hear from couples after their wedding is that they wish they'd just enjoyed being engaged for longer before diving into the logistics of planning.

So here's my advice: get engaged. Celebrate. Enjoy it. And then wait a bit before you start planning. Wedding Planning can be very unromantic Let's be clear about what wedding planning actually is: it's project management with a budget that never goes as far as you think it will.

Within the first month of planning, you're going to have conversations that are decidedly unromantic. You're going to talk about money with your partner. You might have to talk about money with your family. You're going to realize that the number you had in your head bears no resemblance to what things actually cost. You're going to have to make a guest list, which means deciding who makes the cut and who doesn't. You're going to have debates about whether you need to invite your dad's college roommate or your partner's cousin you've met exactly once. You're going to talk about napkin colors and rentals and whether you need a shuttle and what time the band should start playing. None of this is the stuff of romance novels.

The Engagement Period is Special

Being engaged is its own chapter. It deserves time and space before you turn it into a year-long project with deadlines and vendor contracts.

This is the time when you get to just be excited. You get to tell people your news and see them light up. You get to wear your ring and feel that little thrill every time you look at your hand. You get to call someone your fiancé for the first time and feel how special that is.

This is the time when people ask you about the proposal story, not about whether you've booked a photographer yet. When you can go to dinner and talk about your future without also talking about whether you can afford the venue you want.

Give yourself permission to live in this moment before it becomes a series of tasks to complete.

The Budget Conversation Comes Fast

One of the first things you'll do when you start planning is have the budget conversation. And it's going to be less fun than you think.

If you're paying for the wedding yourselves, you're going to have to talk about what you can actually afford and what you're willing to spend. Those aren't always the same number.

If your families are contributing, you're going to have to have potentially awkward conversations about who's paying for what and whether that comes with strings attached. It often does.

And then you're going to start getting quotes from vendors and realize that everything costs more than you thought it would. The flowers you saw on Instagram? Those were $15,000. The band you loved at your friend's wedding? They're $12,000. The venue you've been dreaming about? It's $20,000 before you've even added anything to it.

This is all fine. It's part of the process. But it's not the romantic, dreamy part of getting married. It's the logistics part.

The Guest List is Its Own Battle

And then there's the guest list.

You think you'll have a small wedding until you start actually making the list. Then you realize you have 40 people in your immediate family. Your partner has 35. You each have 20 close friends. That's 95 people before you've invited a single coworker, extended family member, or family friend.

Suddenly you're having conversations about who you can cut. Do you invite kids? Do you invite plus-ones for everyone or just people in serious relationships? What counts as a serious relationship? Do you invite your parents' friends?

These conversations are necessary, but they're not fun. They're full of compromise and sometimes tension.

Here's What We Recommend

Get engaged. Take three months, six months, even a year to just be engaged before you start planning in earnest.

Travel together. Go to dinner and talk about what you want your life to look like. Spend time with the people you love and let them celebrate with you. Enjoy the fact that this is a special time in your relationship that you only get once.

When you do start planning, you'll still have plenty of time. Most venues and vendors book 12 to 18 months out, some even less. You don't need to book everything the week after you get engaged.

And when you do start planning, hire a planner who can help you navigate the budget conversations, the guest list debates, and all the logistics so you can focus on staying connected to each other and to why you're doing this in the first place.

The Wedding is One Day

I know this is what every wedding planner says, but it's true: the wedding is one day. The engagement is a chapter. The marriage is the rest of your life.

Don't rush through the engagement to get to the wedding. The engagement is good too. It's worth savoring.

Plan the wedding when you're ready to plan the wedding. But give yourself time to just be engaged first. To sit with the joy of it. To let it be simple and romantic before it becomes complicated and logistical.

You'll be glad you did.