Guide
What an engagement session is actually for
The photographs are the smaller half of it. An engagement session is the hour where you find out what being photographed together feels like, before it matters. What to wear, where to go, and when to book it.
July 30, 2026
The photographs are the smaller half of the reason to do this. The bigger one is that an engagement session is a cheap, low-stakes hour in which you find out what being photographed together actually feels like, and I find out how the two of you behave around a camera. On a wedding day none of that can be rehearsed and none of it can be redone. Doing it once beforehand is the single most useful thing you can do for your wedding photographs, and it costs you an evening.
What is an engagement session actually for?
Three things, in order of how much they matter.
It takes the strangeness out. Almost nobody is comfortable in front of a camera at first, and almost everybody is fine twenty minutes in. That twenty minutes has to happen somewhere. Better here, in normal clothes on an ordinary evening, than during the only hour of your wedding day set aside for the two of you.
It tells me how you work. Whether you laugh when you are nervous, whether one of you goes still, whether you are the couple who need a task or the couple who need to be left alone. I would much rather know that already.
It gives you photographs of now. You will have wedding pictures. You will not otherwise have many pictures of this particular stretch, the one where you are engaged and nothing has happened yet.
What should you wear?
Clothes you already own and already like. The sessions that go badly are the ones where somebody bought an outfit for it and spends the hour aware of the outfit.
- Coordinate, do not match. Two people in the same shade of blue reads as a school photograph. Related colours in different weights looks like two people who got dressed in the same house.
- Avoid big logos and tight repeating patterns. Fine stripes and small checks do strange things at certain distances.
- Comfortable shoes. This matters more than anything else on the list. We will walk further than you expect and nobody looks relaxed while their feet hurt.
- Bring a second option if you want one, but one outfit you feel good in beats two you are unsure about.
- Layers in autumn and winter. A blanket is not a prop, it is how you stay out for the last twenty minutes of light.
Where should you go?
Somewhere that means something to you beats somewhere that photographs well. I can make almost anywhere work. I cannot manufacture the way you behave in a place you actually care about.
That said, the practical categories around here:
A town
Brick, stone, storefronts, steps. Shepherdstown is full of it and so is downtown Frederick along Carroll Creek. Towns are good when the weather is uncertain, because there is always somewhere to stand.
A ridge or an overlook
The Blue Ridge is half an hour from most of where I work. Overlooks give you distance and sky, and they are worth the walk if you are both up for one. They are also exposed, so it is a plan that wants a weather check.
Ashley and Alan's session was up on the rocks at Weaverton Cliffs, which is a genuine hike in real shoes and repays it. We started in the last of the sun and stayed out well past it.
A field, a farm, or water
Open ground in the last hour of light is the most forgiving thing there is, and the Potomac and the Shenandoah are never far away in this part of the world.
Your own house
Underrated and increasingly the one I suggest first. Your kitchen, your dog, your terrible sofa. Nobody has to travel, nobody is performing, and in ten years it will be the set of pictures you are gladdest to have.
When should you do it?
Book it around the light, not around the clock. The hour before sunset is the easy answer and it is easy for a reason. Sunrise is better for privacy if you are going somewhere popular, and it is the only way to have an overlook to yourselves.
On timing relative to the wedding: far enough ahead that the pictures are still useful. If you want them on save-the-dates, count backwards from when those go out and add a few weeks for editing. If you have no such deadline, the honest answer is whenever the season you want is happening.
And stay out past the point where it looks finished. The twenty minutes after the sun has gone are the ones most people pack up through, and they are frequently the best of the evening.
What actually happens during it?
Less direction than you are probably imagining. I will tell you where to stand and occasionally what to do with your hands, because everybody needs that, and then largely leave you to it. Walking and talking produces better photographs than posing, so a lot of the hour is the two of you moving around and me staying out of the way.
It runs about an hour of real photographing. Allow more in your evening than that if we are moving between two places.
What I will not do is turn up with the light already decided. I plan for it and then read what the evening is actually doing, which is the same way I work on a wedding day, and part of why doing this once first is useful.
Where do you photograph engagement sessions?
Around Shepherdstown, Martinsburg and the Eastern Panhandle, over to Harpers Ferry, and out into Frederick, the Shenandoah Valley and Northern Virginia. Travel is included across that whole region, so where we go is a question about what you want rather than what it costs.
If you have not booked a wedding photographer yet, the pricing page has how everything works, and there is a longer piece on what wedding photography actually costs and why. If you have, and you are wondering whether to add a session, the answer is usually yes and the reason is the first paragraph of this page.
Two other things worth reading while you are planning: how long wedding photographs actually take, which is less than most timelines assume, and what a second location really costs you.
When you have a date, or even a rough idea of one, send it over.
Common questions
Is an engagement session worth it?
The photographs are the smaller half of the reason. The bigger one is that it is a low-stakes hour to find out what being photographed together actually feels like, and for me to learn how the two of you behave around a camera, before the day where none of that can be redone.
What should you wear to an engagement session?
Clothes you already own and already like. Coordinate rather than match, avoid loud logos and tight repeating patterns, and bring a second option if you want a change. Comfortable shoes matter more than almost anything else, because you will be walking.
How long does an engagement session take?
About an hour of actual photographing is plenty. Allow more than that in your evening if we are moving between two spots, and plan around the light rather than around the clock.
When should you book an engagement session?
Far enough ahead of the wedding that you have the pictures while they are still useful. If you want to use them for save-the-dates, count backwards from when those go out, then add a few weeks for editing.
Where do you photograph engagement sessions?
Around Shepherdstown, Martinsburg, Harpers Ferry and the Eastern Panhandle, and out into Frederick, the Shenandoah Valley and Northern Virginia. Somewhere that means something to you beats somewhere that photographs well.