If you’ve ever scrolled through a photographer’s website at 11pm wondering whether you should reach out, you’re not alone. I get questions every week — some over email, some whispered during sessions, some I can practically see forming on a client’s face before they say a word. So I thought I’d pull back the curtain and answer the ones that come up most often, including a few I wish more people would ask.

Whether you’re booking a family session down the road from me or flying me out for a destination shoot, my hope is that this gives you a little more clarity (and maybe a little less anxiety) before we ever meet. Ready for the top 5 questions I get asked as a portrait photographer? Let’s go! 

1. “What should I wear?” — but the version most people are actually Googling

The honest, most-Googled version of this question is usually: “What should I wear for family photos to look skinnier?” or “What colors photograph best?”

I used to answer the surface question. I’d send a Pinterest board, talk about neutral palettes, suggest avoiding logos, the usual. But here’s what I’ve learned: when someone asks about clothing, they’re rarely asking about clothing. They’re asking, “Will I look like myself in these photos? Will I like what I see?”

So now I answer the real question. Yes, certain fabrics drape more flatteringly. Yes, coordinating tones (not matching) photographs beautifully. But the bigger truth is this: you will love your photos most when you wear something you already feel good in. Not the outfit you bought specifically for the session and are still tugging at. The dress you wore on date night that your partner couldn’t stop looking at. The sweater that feels like a hug. That’s what reads on camera — comfort in your own skin.

If you want a starting point, I send every client a personalized style guide once they book, and we usually hop on a quick call to talk through it.

2. The thing about portrait photography I didn’t understand until I’d done it for years

Early in my career, if you’d asked me what made a great portrait session, I would’ve said good light, a beautiful location, and a relaxed client.

I still believe all of that. But here’s what I genuinely believe now that I don’t think I would’ve said out loud in my first year: most of my job isn’t taking pictures. It’s making people feel safe enough to be themselves in front of a camera.

The technical stuff — exposure, composition, posing, editing — is the price of admission. Every working photographer can do those things. What separates a session you tolerate from a session you love is whether the person behind the camera notices when your shoulders are creeping up to your ears, when the toddler is about to melt down and we need to pivot, when you and your partner haven’t actually looked at each other in twenty minutes and a real laugh is overdue.

I didn’t learn that from a workshop. I learned it from watching the same family come back year after year and realizing they weren’t booking me for my gear. They were booking me because their kids felt easy around me. That changed how I approach every single session now — local or destination, two people or twelve.

3. “How long until I get my photos?” — and the question I wish you’d ask instead

This is the question almost everyone asks before booking, and I get it. You’re investing real money and you want to know when you’ll actually see what you paid for. So I always answer it honestly and upfront: my standard turnaround is 3–4 weeks for galleries, with a handful of sneak peeks within 48 hours. Destination sessions sometimes run a touch longer because of travel and editing volume, and I’ll always tell you that before you book — never after.

Being clear about timelines tends to put people more at ease than anything else I say, because it removes the one variable they can’t control.

But here’s the question I wish more clients asked before their session:

“What does a session with you actually feel like?”

Almost no one asks this, and it’s the thing that matters most. Are we walking and chatting, or standing in posed setups? Will you direct me, or do I need to know what to do? What if my kid won’t cooperate? What if I cry? What if I hate having my picture taken and only booked this because my mom asked for an updated family photo?

All of those are real things clients have told me after the session, and every time I think: I wish you’d asked me first, because I would’ve told you exactly what to expect and you would’ve spent the week beforehand excited instead of anxious.

So — if you’re considering booking a portrait photographer (me or someone else), ask them what the experience feels like. Their answer will tell you more about whether you’re a fit than any portfolio image ever could.

4. “Do you help with posing? I’m so awkward in photos.”

Yes. Always yes. And if it helps: roughly 90% of the people who tell me they’re “awkward in photos” are not actually awkward — they’ve just been photographed badly or told to “act natural,” which is the least natural instruction in the English language.

I give gentle, specific direction. Tilt your chin toward your daughter. Walk toward me but look at each other. Whisper something only he can hear. You won’t be left standing there wondering what to do with your hands.

5. “Is it worth flying you out for a destination session?”

I’m biased, obviously. But here’s the honest answer: it depends on what you want the photos to mean.

If you want documentation of a specific place — a milestone trip, a proposal location, the beach where you got engaged — then yes, bringing in a photographer who already knows your style is almost always worth it over hiring someone local sight unseen. If you just want pretty photos and the location is flexible, you can absolutely save money by booking closer to home.

I travel for sessions regularly and I’m happy to talk through whether it makes sense for what you’re hoping for. Sometimes I’ll even tell people it doesn’t — because the goal is photos you love, not a bigger invoice.

Still have questions? That’s a good sign — it means you’re thinking carefully about who you want to trust with this. Reach out here and let’s chat about your session, whether it’s around the corner or across the country. P.s. if we’re not friends on social media, we should be! @brookebakken