Congratulations. Truly. Take a moment, call your people, and stare at the ring for a while.
Then, somewhere around day three, the questions start. Where? When? How many people? Do we need a planner? Is it too early to book a photographer? (Spoiler: it's probably not.)
Before I picked up a camera, I worked for a wedding planner, and I watched a lot of couples go from engagement-high to overwhelm in about a week. The couples who stayed calm weren't the ones who did more. They were the ones who did the right things in the right order. Here's the order I'd follow.
Week 1: Enjoy it, and have the big conversations
You don't need a Pinterest board yet. You need three honest conversations with your partner:
1. What matters most to us? Pick your top two or three: the food, the music, the photos, the venue, having everyone you love in one room. This is the most useful thing you'll decide, because every budget question later gets easier when you know what you're protecting.
2. What's our rough guest count? A ballpark is enough. Whether it's 40 or 160 changes your venue options, your budget, and the whole feel of the day. (If you want to think this through carefully, my post on building a guest list that feels like a party is a good place to start.)
3. What's our budget, and who's contributing? It's not the romantic part, but it's the part that prevents arguments in month six. Talk about it early, and talk about it kindly.
Week 2: Pick a season and start touring venues
Once you have a guest count and a budget range, choose a season or a few possible months. In Chicago, this matters more than people expect. Peak dates at popular venues can book a year or more out, and the difference between a Saturday in October and a Friday in March can be significant.
Be flexible where you can. A Friday, a Sunday, or an off-peak month can open up venues that otherwise wouldn't fit your budget. When you tour, ask each venue:
- What's included, and what do I need to rent separately?
- What's the rain or weather plan?
- What are the ceremony and reception end times?
- Where could we take portraits on-site if the weather is rough?
That last question is one I'd love every couple to ask. A venue with a beautiful staircase, a big window, or a covered terrace is a venue that photographs well even on a gray day.
Week 3: Lock in the vendors that book first
You don't have to hire everyone at once. But a few vendors tend to book earliest because there are only so many of them per date: your venue, your photographer, your planner or coordinator if you want one, and your band or DJ.
Photography belongs in that first group for a reason. Your photos are one of the only things that last after the day ends, and the photographers whose work you love are usually the ones with full calendars. Reach out as soon as you have a date, even a tentative one. Ask about availability, what's included, and how they work with the timeline on the day.
Week 4: Build the foundation, not the details
By the end of the month you don't need a color palette or a favor idea. You need a simple foundation:
- A date (or a short list of dates)
- A venue booked, or a shortlist narrowed to two or three
- A budget everyone understands
- A first draft of your guest list
- A couple of vendors on hold
That's it. Everything else, the florals, the invitations, the cake, flows naturally from those decisions, and you'll make better choices about all of it with a solid foundation under you.
One thing I tell every couple
The best advice I can give from my planner days: the day goes smoothly because of the decisions made months earlier, not the ones made the week of. A realistic timeline, a venue that fits your guest count, vendors you trust, and a plan for the weather mean you get to be present on the day instead of managing it.
And if you're planning a Chicago wedding and want a photographer who thinks about the day the way a planner does, I'd love to hear about it. Reach out through my contact page and tell me your date, your venue, and what matters most to you. That first conversation is always one of my favorite parts.
