July 21, 2026

I met Grace and Landon in a field just outside Winston-Salem a few months before their wedding, the grass still damp enough that it soaked through the hem of Grace’s dress within the first ten minutes. Landon barely said a word when they first got out of the car. He answered my questions with a nod or a short “yeah,” and every time I asked him to hold Grace a certain way, he’d glance at her first, like he was checking if it was okay. I remember thinking this was going to be a quiet shoot. But somewhere around the halfway mark, after I’d stopped directing so much and just let them walk the field together, Landon started talking. Not a lot, but enough. By the time we lost the light, he was cracking jokes and Grace was laughing at things he said before he even finished saying them. We felt like friends by the end, not photographer and clients. That shift, from barely speaking to genuinely at ease, is the entire reason engagement photos exist.
An engagement session is a portrait session for an engaged couple, usually shot a few months before the wedding, and its real job isn’t to produce a pretty Save the Date card. Its real job is to teach two people how to exist in front of a camera together before the most photographed day of their lives shows up. I know that sounds like a strange thing to need practice for, but most people have never had a stranger with a camera study them for an hour. It’s a skill, and like most skills, it gets better with a trial run.
Yes, and the difference shows up in ways clients don’t expect. Couples who’ve done a session with me arrive on their wedding day already knowing where to put their hands, how close is too close, and what my “look at each other like nobody’s watching” direction actually means in practice. During the session, I get to watch how a couple naturally touches each other, whether he’s a forehead-to-forehead kind of guy or she likes to grab his shirt collar when she laughs, and I file all of that away. On the wedding day, when we’ve got twenty minutes squeezed between the ceremony and dinner, there’s no time to rebuild that trust from scratch. We’ve already built it. If you want a deeper look at how I structure that limited wedding day window, I wrote about it in my guide to building a realistic North Carolina wedding day timeline.
Comfort matters because tension photographs. It doesn’t matter how good the light is or how well-tailored the suit fits, if a couple feels awkward, the camera catches it. I’ve had grooms tell me, almost sheepishly, that they hate having their picture taken. That confession usually comes out about twenty minutes into a session, right after they’ve forgotten they’re being photographed at all because we’re walking and talking instead of posing. A good engagement session isn’t really about hitting marks and holding a pose. It’s about giving two people forty five minutes to just be a couple while I quietly document it.
My honest answer is wherever feels like you, not wherever is trending on Pinterest that month. That said, this city gives us a lot to work with. Old Salem’s brick sidewalks and log buildings photograph beautifully in that late afternoon light, especially in the colder months when the crowds thin out. Bailey Park downtown has that industrial-meets-green-space feel that works well for couples who want something more modern. And if someone tells me their families both grew up going to Tanglewood Park, we’re heading straight there, because a location with a story behind it always outperforms a location that just looks nice. I keep a running list of favorite spots in my engagement session guide with locations around Winston-Salem if you’re trying to narrow it down.
Weather rarely ruins a session, it just changes it. I shot a session in February with Sylvia & Boone where the temperature sat around 38 degrees and neither of them had dressed warmly enough, and honestly some of my favorite frames came from that shoot, the two of them huddled together, both of them a little pink in the cheeks and laughing about how bad an idea this was. A gray sky acts like a giant softbox and evens out shadows on faces in a way direct sun never will. I do keep an eye on hourly forecasts through a tool like the National Weather Service’s forecast page when we’re deciding on timing, mostly to avoid thunderstorms rather than clouds, since clouds are rarely the enemy people assume they are.
They give you real, current photos to use for the Save the Date, the wedding website, and honestly your own social media before the big day, but there’s a second benefit people overlook. The session becomes a low stakes rehearsal for working with your hired photographer as a vendor. You learn how I communicate, how I move a group along without feeling rushed, and whether my style actually matches what you pictured when you booked me. If it doesn’t feel right, better to know that seven months out than to discover it during the reception.
Wear something that feels like your actual closet, just a slightly elevated version of it. I generally steer couples away from matching outfits and toward complementary tones instead, and I always ask what the wedding’s color palette looks like so we’re not accidentally clashing with it later. Layers help a lot here because our fall and spring days can swing fifteen degrees between morning and afternoon.
For most couples, yes, and not for the reason people assume. It’s not really about getting more photos for your money. It’s about what those photos do for the wedding day itself. A couple who’s spent an hour being coached through eye contact, walking, and quiet conversation with me shows up on their wedding morning already knowing how this works. That translates into more genuine expressions during formal portraits, a calmer couple during the fifteen stolen minutes after the ceremony, and photos that actually look like the two of them rather than two people performing what they think a wedding photo should look like. As a side note, all of my wedding packages include a discount towards and engagement session, so it’s super easy to add on! 🙂
Back to Grace and Landon for a second, because the small stuff is what stays with me. There was a stretch near the end of the session where neither of them said anything at all, they just stood in that field with the tall grass brushing against their legs, foreheads together, and I remember lowering my camera for a second just to let it happen instead of shooting through it. None of that was planned or directed. On their wedding day, months later, I didn’t have to coach them into that same closeness. They found it on their own, in the middle of a room full of eighty guests, like they’d been doing it their whole lives. They were pros by then. Landon, the same guy who’d barely spoken to me in that field, was the one cracking jokes with the groomsmen and pulling Grace in for a dip during their first dance without me saying a word.
If you’re engaged and thinking about booking a Winston-Salem engagement session, I’d love to hear where your story started and figure out where the photos should start too. For couples still deciding between photographers, Brides has a reasonable overview of questions to ask before you sign a contract, and it’s worth a read alongside whatever portfolios you’re comparing.
Hi there,
I’m a wedding and family photographer based in Winston-Salem, North Carolina, ready to capture every season of your life. My approach is warm, nostalgic, and focuses on what makes you you. I would love nothing more than to document your memories, together.
Your life is a beautiful, unfolding narrative, and I’d love to help you capture it. If you’re planning a wedding, engagement, or family session, let's chat so we can start crafting your very own visual legacy. Together, we’ll create images that you and your loved ones will treasure for generations.
Authentic storytelling of your life's precious moments
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