Engagement photos in NYC tend to get planned backwards. People start with the location, usually the one they saw on Pinterest, and work outward from there. I would start somewhere else: with what the two of you are actually like together, and with the light.
The location matters, but it matters less than the two decisions either side of it. Here is how I would plan the session.
Pick a place with a reason behind it
The strongest engagement photos I take are almost never in the most photogenic spot in the city. They are in the place the couple already goes.
The block where you met. The bar you walked to in the rain. The stretch of the promenade you end up on every Sunday. When people are somewhere they know, they stop performing within about ten minutes, and everything after that is easier. When they are somewhere they have never been, standing in front of a landmark, it takes longer.
If nowhere jumps out, that is fine, and there are locations that reliably work. Brooklyn Bridge Park and DUMBO for the skyline. Central Park for green space and architecture in one walk. The West Village for narrow streets and doorways. Fort Tryon Park if you want to be away from crowds entirely.
One thing worth knowing: the most famous frames in this city are famous, which means other people are standing in them. The cobblestone view of the Manhattan Bridge in DUMBO has a queue on a Saturday. It is still worth doing, just go early.
Two locations, not five
A one-hour session realistically covers one neighbourhood, or two spots within a short walk of each other. Every extra location costs you fifteen minutes of walking and a change of gear, and that time comes straight out of the shooting.
The pairing I would suggest: somewhere open for the wide, romantic frames, and somewhere with texture and structure nearby for the closer ones. A park and a street. A waterfront and a set of arches. That gives you variety without spending the session on the subway.
Time it around the sun, not your calendar
Aim to start about ninety minutes before sunset. That window gives you warm, low, directional light, and it is the difference between photos that look like your engagement and photos that look like a Tuesday lunch break.
In summer that means starting around 6:45 or 7pm, which is easy after work. In late autumn and winter it means late afternoon, and you will need to take time off or use a weekend. Check the sunset time for your date before you agree a slot. The golden hour guide has the seasonal breakdown.
Early morning is the underrated alternative. The light at 7am is nearly as good, DUMBO and the Brooklyn Bridge are close to empty, and you get the city to yourselves. It is a real trade for anyone who does not want to be photographed with two hundred tourists in the background.
If the forecast turns grey, do not panic and do not automatically reschedule. Overcast light is soft, even, and very kind to skin. Light rain is worth shooting through if you are willing, and an umbrella in the frame is not a compromise.
What to wear
Coordinate rather than match. Choose one palette between you, keep patterns quiet, and let one of you carry the stronger colour. Fabrics that move, like a dress with some length or a soft overshirt, give the photos life when there is wind coming off the water.
Two outfits is plenty for an hour, and only if you can change without a hunt for a bathroom. Bring shoes you can walk several blocks in, especially if there are cobbles involved. The couples outfit guide covers the whole thing in more detail.
One small thing worth doing: get your ring cleaned the week before. It photographs very differently, and there will be at least a few frames where the hands are the subject.
What actually happens in the hour
Very little standing still, and almost no posing in the way people fear. Most of the session is walking, talking, and being given something to do: a direction to walk in, a question to answer, a reason to look at each other rather than at me.
The first ten minutes are usually the stiffest, and that is normal for everyone. It is why I do not start with the frame I care most about. By twenty minutes in, people have forgotten the camera is there, which is when the photographs start being about the two of you rather than about being photographed. If that part worries you, this post on feeling natural in front of the camera is the one to read.
Bring something to do if you want a break from portraits: coffee from a place you like, a bench, a dog. Sessions with a small activity in them tend to produce the frames people end up printing.
The practical notes
Public parks and streets are fine for a normal session with a photographer and a couple. Some venues and gardens require a permit or a paid photo pass, so check before you commit to a specific interior. The post on shooting at the Met goes through how that works in a museum.
Book earlier than feels necessary for autumn dates. Late October and early November weekends go first, and once the clocks change on November 1 the usable light ends before most people finish work.
Photos arrive in a private gallery, generally within five to seven business days. Plenty of couples use a few of them for save-the-dates, so if you have a print deadline tell me at the booking and we will work back from it.
If you have a date or a neighbourhood in mind, send me a message and we can build the plan around it. The couples session options list what each one includes.