10 Questions to Ask Your Wedding Photographer Before Booking (and What I Wish Couples Asked Me)

When you’re planning your wedding, choosing your photographer is one of the most personal — and important — decisions you’ll make. Your photos are what will tell the story of your day long after it’s over, so finding someone who truly gets you matters.

But how do you know what to ask before signing the contract?

Here are ten questions that will help you go beyond the basics and find the photographer who fits your vision, your energy, and your story — plus a few things I wish couples asked me before booking.

1. Can we see a full wedding gallery — not just highlights?

Every photographer can show a handful of dreamy portraits on Instagram. But seeing a full gallery gives you a better idea of how they capture every part of the day — from quiet getting-ready moments to your wild dance floor photos. It’s the best way to understand their storytelling consistency and range.

2. How would you describe your shooting style?

Is it documentary, editorial, fine art, or a blend? Understanding your photographer’s creative approach helps set expectations.

For me, I’d say documentary with an editorial edge — a mix of honest, emotional storytelling and intentional, timeless composition.

3. How do you help couples feel comfortable in front of the camera?

If you’re not used to being photographed (and most people aren’t), this is key. Ask how your photographer gives direction, reads energy, and creates natural moments.

What I wish couples asked me: “How do you help people be themselves?” Because that’s the heart of what I do — creating space for genuine emotion instead of stiff posing. It looks like having conversation and taking breaks in between direction. It looks like giving feedback when I like what I see. It’s also sometimes not saying anything at all and letting you be who you are in that moment.

4. What’s your backup plan if something unexpected happens?

Boston has a mix of venues — from elegant hotels like The Newbury and The Langham, to coastal estates and restaurants with intimate charm. A photographer who’s shot at similar spaces will know how to work with tricky lighting, crowd flow, and timelines. When you browse portfolios, look for full galleries from weddings that resemble your own — not just a highlight reel.

Just because another photographer you’ve talked to has worked at the venue before does not mean that they will necessarily give you a better experience or better photos. Sometimes having a Photographer who has never worked at your venue is great because they see everything with fresh eyes and can offer new perspective.

5. How do you handle low-light or indoor settings?

If your venue is dimly lit or your reception goes late into the night, you’ll want someone confident using flash or creative lighting. Ask to see examples from similar conditions — your photographer should be comfortable working in any environment. This isn’t just to see if they’re comfortable with low light or indoor settings, it’s to see what their low light/flash style is as well. How do they photograph a reception? Is it fun, vintage and you can feel the night? That’s most likely direct on camera flash. Or is it drama and even well cinematic lighting? That could me off camera lighting equipment that’s set up around the venue.

6. What’s your turnaround time for receiving photos?

Every photographer’s timeline is different. Some deliver previews within a week; others take several months for final edits. Ask when you can expect sneak peeks and full galleries — so you know what’s coming after the big day. Time of year, experience and demand all play roles into the length of time it takes to get your final gallery back.

I take around 15 weddings a year so that I can ensure that my couples receive their galleries in a timely manner. Most Weddings I like to deliver within 6-8 weeks depending on the time of year.

7. Can we customize a package to fit our day?

No two weddings are alike. If you are having a smaller wedding or no bridal party than maybe you don’t quite need a 10 hour day.

What I wish couples asked me: “What would you recommend for our day based on the timeline?” I generally know right away what a client will need based on conversation on the discovery call. I definitely think custom proposals are the way to go for couples that are planning a little bit of a non traditional day.

8. How do you approach family photos and group shots?

Even couples who love candid moments still want classic family portraits. Ask how your photographer keeps things organized but natural. A little planning here makes the day flow smoother — and keeps everyone smiling. Family Portraits can be the more chaotic portion of the photo timeline. I have a great system that has worked for many years.

9. What’s your editing process like?

Editing style defines a photographer’s look. Ask how much editing they do will help you get educated on what to expect. This is why viewing a full gallery is so important. You can see the tones they use, how much photoshop they involve and how they communicate your story through the editing process.

What I wish couples asked me: What do you describe your editing style to be?

This is actually important because color and tones sometimes can be subjective. What someone might call natural tones others can call moody.

10. What’s most important to you when photographing a wedding?

This question goes deeper than logistics — it’s about values. You’ll hear what drives their work and how they see storytelling.

What I wish couples asked me: “What do you look for on a wedding day?”

My answer: I value couples who prioritize connection and meaning. The emotion, in-between gestures, and moments no one else notices — the ones that make your photos uniquely yours. Staging moments or forcing trends for the sake of tradition is what can leave your images looking stale and lacking emotion. It also can be hard to capture real genuine moments for a photographer if someone has different values than this.

Final Thoughts

When you meet with a photographer, remember it’s not just about comparing packages or styles. You’re choosing someone who will be by your side all day — witnessing, guiding, and preserving the moments you’ll never get back.

The right photographer isn’t just a vendor — they’re a storyteller, a calming presence, and someone who understands what matters most to you.

If you’re currently looking for a wedding photographer in Boston or New England, I’d love to connect. I’m happy to walk you through my process, share full galleries, and help you figure out what will make your photos feel most you.

x Cory