Two Hundred Photos of a Golden Retriever: The Booking Requests That Made Me Laugh (and Say Yes)

If you've read this blog for any length of time, you know I love the big moments — the first kiss, the fog rolling over the Blue Ridge at sunrise, the toddler who finally cracks a smile in the third hour of a family session. But what I don't talk about enough are the requests. The inbox emails that make me put down my coffee and read them twice.

Every photographer I know has a mental folder of these. Mine is full. So today, in the spirit of full disclosure (and because it's Friday and I feel like it), here are a few of my all-time favorites — and what each one taught me about this strange, wonderful job.

The 200-Photo Dog Commission

Let's start with the headline act. A client — lovely woman, great taste, clearly devoted — booked a portrait session for herself and then, halfway through planning, added a footnote: "Also, could you get around 200 photos of my dog? He's kind of the whole reason I'm doing this."

Two hundred. Not fifty. Not "a few good ones of Biscuit." Two hundred.

Here's the thing: I said yes. Not because 200 is a magic number, but because I asked a follow-up question — why — and the answer was heartbreaking and beautiful. Biscuit was fourteen, had a diagnosis with a timeline, and she wanted everything. Every gray muzzle hair, every head tilt, every nap in the sunbeam. We got her closer to 300. I've never worked a session where the client cried more, and I've never been happier to overshoot a deliverable.

The lesson: Sometimes a weird request is just a weird request. Sometimes it's a person telling you what actually matters to them in the only way they know how. Ask the follow-up question before you price the job.

The Best Man Who Wanted to Be Invisible

A groom once asked me to photograph his wedding but to "pretend the best man doesn't exist." Turns out the best man had a habit of photobombing, and the couple wanted zero evidence. I explained that I can't control another adult's behavior all night, but I could position myself strategically, shoot tighter during toasts, and flag any frame where he wandered into something important. We compromised: I'd deliver the gallery with those images culled unless they asked to see them.

That's the difference between saying yes and saying yes blindly. I couldn't promise the impossible, but I could promise a process.

The Proposal Decoy

This one's my favorite genre. A guy emails me in secret: his girlfriend thinks they're doing a "couples session to update holiday card photos." In reality, he's proposing at the halfway point and wants me to capture her face at the exact moment she figures it out.

I've shot four of these now, and every single one is a joy. The trick is logistics, not photography — knowing where he'll kneel, where the light is, where she'll be looking. One took place at a vineyard outside Charlottesville in October; another on the Georgetown waterfront with a very suspicious girlfriend who almost figured it out twice.

If you're planning one: tell your photographer everything, including the cover story, so we don't accidentally blow it by asking the wrong question in front of her.

When I Say No (and You Should Too)

Not every request gets a green light. I've turned down "just remove my mother-in-law from this photo entirely" (she was in the background of a wide shot, and erasing a human being felt like a line), "make me look like I did in college" (I'll make you look like the best version of now, not a different decade), and one request to shoot a wedding solo from a golf cart because the venue "didn't want people walking on the grass."

Here's my rule of thumb: I'll bend the process, but not the product. If a request changes how I work but still gets you honest, beautiful images — sure, let's get weird. If it compromises the images themselves, or my integrity in making them, I'll tell you kindly and offer an alternative.

Clients respect that far more than a reflexive yes. The ones who don't were going to be a problem anyway.

So, What's the Weirdest Request You've Gotten?

I get asked this at almost every consultation, and honestly, the dog count barely cracks my top three. There was the couple who wanted their first dance photographed only from the balcony "for the drama." The family who brought a ladder to the beach. The bride who requested I learn her grandmother's favorite hymn so I'd know when it was coming during the service.

That last one I did. I'm a terrible singer, but I knew exactly when to raise the camera.

The through-line in all of this? Great client relationships aren't built on saying yes to everything. They're built on listening hard enough to understand what's actually being asked — and having the confidence to say "yes, and here's how" or "no, but here's what I can do."

Got a strange request of your own? Send it over. Biscuit's mom did, and it made my whole year.

— J.