You’ve been scrolling through wedding photographer portfolios for weeks. Maybe months. And here’s the thing – they all look beautiful. Dreamy golden hour shots, tearful first looks, stunning detail flats. So how are you actually supposed to choose?
Here’s what I’ve learned after photographing hundreds of weddings: the difference between a good wedding photography experience and a frustrating one rarely shows up in a portfolio. It shows up in how your photographer works with you, how they handle the unexpected, and whether they truly understand what makes a wedding day flow.
Before you sign any contract, ask these five questions. The answers will tell you everything you need to know.
1. “How do you handle family formal photos?”
Why this matters: Family formals can either take 15 focused minutes or turn into a 45-minute chaotic mess that eats into your cocktail hour. Ask me how I know.
What you’re really asking: Are they organized? Do they have a system? Will your family actually listen to them?
What a good answer sounds like: Your photographer should have a clear process – whether that’s a shot list you create together beforehand, how they wrangle large families efficiently, and how they keep things moving without making anyone feel rushed. They should mention working with your coordinator or having an organized family member help gather people.
Red flag answer: “Oh, we just figure it out as we go!” or anything that suggests they’re winging it.
At my weddings, we create a prioritized family photo list together during our planning timeline, I coordinate with your planner on timing, and I bring that calm-but-confident energy that gets even the most chaotic families organized quickly. Because you shouldn’t spend your cocktail hour hunting down Uncle Bob.
2. “What happens if you’re sick or there’s an emergency?”
Why this matters: Life happens. COVID taught us that. Your photographer needs a backup plan that doesn’t involve crossing their fingers and hoping for the best.
What you’re really asking: Do they have insurance? A network of trusted photographers? Will you be left scrambling the week of your wedding?
What a good answer sounds like: They should have a network of professional backup photographers whose work you can review, contracts that outline contingency plans, and insurance that protects everyone. They might mention having a second shooter who could step up, or relationships with photographers they trust implicitly.
Red flag answer: “That’s never happened to me before” or “I’d find someone to cover it.” That’s not a plan, that’s a hope.
I maintain relationships with several talented photographers in Florida whose style aligns with mine. You’d meet them beforehand if possible, see their work, and have their contact information. I also carry backup gear to every wedding – because equipment fails more often than photographers do.
3. “How do you work in challenging lighting situations?”
Why this matters: Not every ceremony happens during golden hour. Not every reception has floor-to-ceiling windows. Real weddings happen at noon in full sun, in dimly lit ballrooms, and during Florida summer storms.
What you’re really asking: Can they actually handle your venue and timeline, or do they only look good in perfect conditions?
What a good answer sounds like: They should talk confidently about working with flash, natural light, mixed lighting, and how they adjust their approach based on conditions. Bonus points if they mention scouting your venue beforehand or asking about lighting during the planning process.
Red flag answer: “I only shoot natural light” (translation: I don’t know how to use flash) or “We’ll just move you to better light” (not always possible during a ceremony or scheduled events).
I’ve shot in nearly every lighting scenario Florida can throw at you – from harsh midday sun to dark romantic ballrooms. I use a combination of natural light and subtle flash to ensure your photos look like you, with accurate colors and flattering light, no matter what time your ceremony starts.
4. “Walk me through what my wedding day timeline looks like from your perspective.”
Why this matters: This question reveals whether your photographer actually understands wedding day flow or just shows up and shoots.
What you’re really asking: Will they help you create a timeline that works? Do they know when golden hour is at your venue? Do they understand how long things actually take?
What a good answer sounds like: They should ask about your ceremony time, sunset time, when you’re doing portraits, and offer insights on how to maximize your photography time without sacrificing guest experience. They might mention buffer time for delays, suggestions for first look timing, or when to schedule family photos.
Red flag answer: “Just tell me when to show up” or anything that suggests they’re not invested in the planning process.
During our planning process, I walk you through a suggested photography timeline based on your venue, season, and priorities. I’ll tell you if your Pinterest-inspired timeline is setting you up for stress, suggest when to do your first look for the best light, and help you understand what you’re trading off if you skip certain photo opportunities. My job isn’t just to document your day – it’s to help you design a day worth documenting.
5. “What’s your approach – do you direct moments or capture them?”
Why this matters: This is about photography philosophy, and there’s no universally “right” answer – but the answer needs to match what you want.
What you’re really asking: Will my wedding photos feel authentic or staged? Will I spend my wedding being posed, or living it?
What a good answer sounds like: They should be able to clearly articulate their style. Some photographers are editorial and highly directed. Others (like me) are documentary-focused. Many are a blend. What matters is that they can explain their approach and show you consistent examples.
Red flag answer: Vague responses like “I do a mix of everything” without being able to show you what that actually looks like in practice.
My approach is documentary with intention. I’m watching for the moments that matter most – the ones you’ll want to remember 20 years from now. I’ll guide you into flattering light and give you gentle prompts during portrait time, but I’m not going to micromanage your expressions or manufacture emotions. You hired me to capture your wedding as it unfolds, with all its imperfect, genuine, beautiful moments. That’s what you’ll get.
The Real Question Behind All These Questions
Here’s what you’re actually trying to figure out: Can I trust this person with one of the most important days of my life?
Your wedding photographer isn’t just a vendor – they’re the one person who will be with you for nearly every moment of your wedding day. They need to be organized enough to keep things running smoothly, experienced enough to handle the unexpected, and intuitive enough to capture what matters without you having to direct them.
The right photographer won’t just have a beautiful portfolio. They’ll have answers to these questions that make you feel confident, informed, and genuinely excited to work with them.
Ready to chat about your wedding? Click the inquire button and let’s schedule a discovery call.
Venue: The Club at the Strand, Naples, Florida
Planner: Kerrigan Constantino Weddings
Photo: Amanda Michelle Photo
Video: MSM Image
HMU: Give Me Glam
Cake: Mikkelson’s Pastry Shop
Florals: Noble and Wild Florals
Rentals: Pro Event Rental
