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ENGAGEMENT
& PORTRAIT SESSION

planning guide

we’ll have fun, i promise

the engagement session


It’s the perfect chance for us to meet before the wedding, explore a little bit, take a break from planning and document this anticipation–filled time in your lives.

But who said you have to be engaged or married to take beautiful portraits together? Often considered something just for newly engaged couples, I also offer portrait sessions which can occur before a proposal, after a ring, or beyond the vows.

Maybe you just moved in together, said ‘I love you’ for the first time, or got matching tattoos. Maybe it’s your wedding anniversary. Or maybe, you just want to remember this time and how young and in love you were with picture-perfect clarity 40 years from now.

So let’s meet up and run around town (or the woods, the beach, or your bedroom) while documenting this moment—however big or small—in your journey together.

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the basics location clothing hair & makeup misc

the basics:

planning your session

Here’s a loose step-by-step guide to get us started on planning your engagement or portrait session. All of these things are reasonably fluid and may or may not apply to what you want or need, which is okay. And as always, don’t hesitate to let me know if you have questions or even a wild idea for something—chances are I will be totally on board.

01: TIMING

See: Teresa + Thomas’ Sweet San Francisco Engagement Session

  • THINGS TO CONSIDER
  • any preferences you have, re: seasons, holidays, weather
  • late summer & fall is always busy
  • to take place at least 2 months before you need prints
  • sunset = 2-3 hours before

First things first: when should we do this thing?

The exact timing of your engagement or portrait session depends on your personal desires for the photos (i.e.: fall leaves or spring flowers; indoor or outdoor locations; holidays; special wardrobe requests) as well as whether you plan to use them for Save The Dates, invites, a holiday card, your wedding website, or any sort of announcement.

Sometimes we do an engagement session a full year before the wedding, other times it’s mere weeks beforehand, or has even utilized as a pre- or post-wedding portrait session to make the most of a packed day-of wedding schedule. A non-wedding-related portrait session may be more flexible in terms of when to do it, though you may still want the photos for a holiday or gift.

If you need printed images for a specific date or event, it’s best to plan the session to take place a minimum of 2 months before you need them. That way, we have wiggle room for any unforeseen delays (weather, illness, etc).

During the late summer through fall my schedule fills up quickly and my editing queue is often jam-packed, so it’s best to plan anything you might need to have printed for holiday cards as early in the season as possible. I try to schedule engagement sessions on Sundays through Thursdays during the busy season as Fridays and Saturdays are often reserved for weddings, and my editing turnaround for engagement sessions is 3-4 weeks.

Our time together during the session usually lasts 2-3 hours (this includes any travel time between locations, which will need to be taken into account when planning) and we’ll want to think about the sun. Are you hoping for a dreamy sunset during the session? I start by Googling “[date] sunset” and will typically schedule sessions to start 2-3 hours before this time.

02: LOCATION

See: Michelle + James’ Perfectly Portland Engagement Session

  • THINGS TO CONSIDER
  • plan for 2-3 contrasting locations
  • somewhere significant to your relationship is great
  • travel time = candid photo time
  • reach out to businesses/private locations for permission
  • busy/touristy locations can be chaotic
  • not local? visit NYC for your session! or I can come to you!

Where do ya wanna go?

I like to plan for a few different locations during engagement sessions to add variety, as long as it’s logistically possible within the 2-3 hour timeframe. When you start considering locations, it’s important to think about what sort of vibe you’re drawn to and whether you want it to be cohesive or contrast your wedding or other photos you’ve had done. Do you want an urban location, or something in nature? Indoor or outdoor? Intimate or bustling? Sometimes couples come to me with an exact idea of where they want to go, and others have no clue and ask me for suggestions.

We can usually incorporate 2 locations—sometimes a 3rd if it’s nearby—and I try to make sure they contrast each other. Like, we may start at your apartment for some cozy intimacy then head out to the park where you walk your dog for some open green space and natural light. We could start in a warehouse neighborhood and end up overlooking the city from a grassy hilltop, or go from a sunny beach to a dark, cozy bar. Whether we have time for a 3rd location or not, I like to have something in mind as a backup in case one of the other locations doesn’t work out for whatever reason. I also love being able to document the travel time between locations for added fluidity and candid moments, so if we can walk or take the subway or a taxi between them, even better.

It’s nice if at least one location is significant to your relationship or life together: the bar where you had your first date, the lake you walk around together at sunset, the art museum where your partner proposed, or your home. For private locations and businesses it’s important to reach out to the owner or organization for permission beforehand, as well as to ask when their least busy or most convenient time of day for us to swing through is so we don’t disrupt their patrons.

I live in Brooklyn and you’re always welcome to come here for your session if you’re not local. If one of your dream locations is really popular (Times Square, Golden Gate Bridge, Chicago’s Cloud Gate, etc) it’s a good idea to keep this in mind and consider how comfortable you’ll be being photographed with oodles of strangers watching, as well as the unpredictable nature and safety concerns (since I’m running around with expensive camera gear) of these locations. They can often be chaotic, loud, buzzy, and crawling with people, which may or may not be the vibe you’re going for.

If you have a *very* specific image that you want at one of these popular locations, please let me know ahead of time so I can ensure I have the appropriate gear and am able to make a plan. A certain viewpoint or area may look entirely different at different times of day (due to light, weather, crowds) and it would be well worth it for us to consider going early (like sunrise) or on an off-day to ensure we have enough time and proper conditions to make the image you want.

If you’re not in the NYC area and want me to come to you for your engagement session, we can always make this happen! There will likely be a travel fee, but we can figure that out when we’re discussing the logistics.

03: LIGHT

See: Bre + Chris’ Film & Neon-centric Engagement Session in NYC

  • THINGS TO CONSIDER
  • golden hour = flattering + versatile
  • golden hour = start 1-3 hours before
  • golden hour location = arrive 1 hour before
  • no golden hour photos = totally okay!
  • NEON! FLASH! STREET LIGHTS! <3
  • find light nerdery here!

Light: we literally can’t make photos without it.

Shocking to none: my favorite natural light for engagement sessions is probably during golden hour, which you may already know as the last hour leading up until the moment the sun dips below the horizon. I love incorporating this time into engagement or portrait sessions when possible, because it’s just so damn dreamy, versatile, and flattering. If for whatever reason you have an aversion to golden hour light, just let me know and we can totally skip it.

Beyond golden hour, I also love working in daylight, twilight, and artificial light, each of which can revolve around the time of sunset and offer ample opportunities for creativity. As we start planning I’ll look up the time of sunset for whichever days we’re considering to help plan out your day and our session accordingly. The goal is to have a certain location in mind for sunset and to ensure we’re not traveling between locations during that time. So if you want daytime + golden hour photos, we’ll schedule the session to start ~3 hours before sunset and make sure we’re at our golden hour location 1 hour before sunset time.

I love (lovelovelove) playing with artificial light, too, so I will gladly schedule a session specifically with flash, neon, street, or car lights in mind! If we’re planning for light we can only achieve after dark, we’ll still want to check the time of sunset and start either 1-2 hours before or after.

In my Wedding Planning Guide, I went a little overboard and wrote about different types of light if you want more info about planning for specific light.

I love inspiration.

Do you have a Pinterest board that you want to share? Don’t hesitate, send it my way! Gathering inspiration is one of the most exciting parts of the planning process for me and can provide a clearer idea of what you want than trying to say it with words.

Do try to avoid sending me a Pinterest board as a “these are the exact photos and poses we want to replicate” sort of shot list, as I try to maintain a certain flow throughout the session and deferring to a shot list will ultimately distract us all from that. If there are a few special poses or ideas that you would really like us to try to to incorporate, do let me know and we’ll try to work it in.

You can find my general inspiration board here (there are sub-boards for couples and groups in there, too, which are great for weddings!) which lends itself to a general weird vibe I’m drawn to at any given time and try to evoke in my own work.

  • THINGS TO CONSIDER
  • Pinterest = a mood board to communicate a vibe
  • Pinterest ≠ strict shot list that kills the flow
  • a few specific poses you want to try? let me know!
  • i love pinterest

BEHIND THE SCENES:

locations

To avoid the typical crowds at Coney Island, Milena + Vic opted to start their engagement session at sunrise in early May.

As filmmakers, The Metrograph in NYC is a special location to Bre and Chris. They reached out to the management ahead of time to ensure we could shoot there and find out when would be the most convenient time.

Amanda + Mike were totally open to location ideas, so the week before their session I drove around Portland with a friend until these giant cable spools jumped out at me.

I found this beach near SF thanks to Google Maps. Teresa + Thomas told me the general area they wanted to go for photos and I zoomed in until I found something that looked interesting.

help!

we don’t know what to wear!

Somewhat surprisingly, clothing ends up being a source of anxiety when planning an engagement or portrait session. If you’re not sure where to start with your clothing, I’m here to help! But if you’re excited about planning this part and feel totally confident, skip ahead.

limit yourself

To break it down as simply as possible I usually suggest two outfits: one that you would wear to a nice date night, and one that’s more casual. One outfit change (in conjunction with a location change) is okay, but more than that can disrupt the natural flow of the shoot and ends up eating into our photography time. If you want to stick with one outfit that’s totally fine, too!

i’m here to help!

I’m always happy to offer suggestions on clothing if you ask but my main suggestion will always be to wear something clean & comfy that makes you feel confident, badass, and sexy/cute/attractive/[your adjective of choice here]. Sometimes that means you’ll order a new outfit, but I honestly recommend looking into your closet to pull out those favorite, special, tried and true items.

If you want ideas, I love fashion and always keep a Pinterest board full of looks that I personally find fascinating, which you can find here. Heads up: I’m not afraid of color or prints, which might not be your vibe, which is okay because I first and foremost want you to wear whatever feels the most true to you.

don’t forget about your feet!

Comfort is key with footwear, too, so I recommend wearing a comfortable (and cute!) shoe since we have a tendency to do a lot of walking and moving during these sessions and stopping to swap out shoes cuts into the time and the candid flow we’re going for.

Last but not least, pleasepleaseplease try to reach out with any wardrobe questions at least a few days before the shoot so we’re not anxiously texting back and forth at 10pm the night before. If you don’t ask for help, I’ll assume you feel confident in your choices and won’t pester you or tell you what I think you should wear.

a few q’s to ask yourself

Long & flowy dresses, skirts, shirts, or pants are always fun in photos, but too-short or too-tight cuts can lead to a wardrobe malfunction if it’s a windy day, you’re moving a lot, or you don’t wear the style often. If you would be uncomfortable accidentally flashing the camera, consider a longer hem.

If something limits your movement or ability to sit down, definitely reconsider wearing it for the session. I encourage a lot of movement and interaction during photos and too tight or restrictive clothing clothing can hinder your ability to move candidly.

If it’s new, try to give it a whirl (date night, work, grocery shopping) before the session to see if you feel like your best self in it. If you’re constantly pulling at it or adjusting it or feel timid or just not yourself, try to go with something else.

If you want to have one fancy outfit and one more casual, we may want to coordinate the clothing + locations accordingly. That being said, I like breaking rules so maybe a tshirt and jeans in a nice restaurant is the right idea…but for your own safety, please don’t hike in high heels!

I’m capable of some surprising feats of Photoshop magic, but would rather not spend hours editing out the same stain, tear, or bra strap in dozens of photos if it can be avoided. 🙂

help!

what about my hair + makeup?!

Time to pamper!

Take this opportunity to pamper yourself before the session, however that may look to you. If you color your hair, get regular haircuts, facials, or manicures, now would be a good time to schedule those appointments or stock up on sheet masks and your favorite nail polish for some at-home pampering. The more you can do beforehand to feel your best and most confident self will really pay off during the session.

Work with a pro

Those who wear makeup often use this as a chance to do a wedding day makeup test or trial with someone before the big day, which is a great idea! That way we can see how well the look photographs (a note for your makeup artist: I predominantly use natural light but utilize my flash for ~¼ of the day, which may affect which products they choose to use) and it will help you determine whether or not you feel confident or even like it.

Be yourself

On the topic of makeup: unless you wear a full face on a regular basis, I stand by the idea that less is more for your wedding or photo session. If you’re typically a no-makeup or low-key tinted moisturizer and barely-there mascara type, maybe don’t go for huge false lashes, deep contour, and overdrawn lips; you won’t feel like yourself and could be unfamiliar with the necessary touch-ups throughout the day.

Don’t forget about hair!

The same sentiment goes for your hair. You don’t have to wear a formal updo or have “wedding hair” because other couples before you have done that. Do whatever makes the most sense to you and won’t render you completely unrecognizable or uncomfortable on the day and in your photos.

before your makeup trial

I reached out to one of my favorite makeup artists, Lindsey Michelle, to get some professional insight into what you can do to prepare for a makeup trial!

Always come with a clean, moisturized face. Exfoliating the night before can also be really helpful, but use your best judgement when it comes to your skin as you know it best!

Always alert your artist of any sensitivities or allergies you have before your appointment. If you have a special product you use on your skin, let your artist know.

Generally you shouldn’t need to bring any makeup to your appointment but it can’t hurt to check with your makeup artist beforehand to make sure you’re prepared. 

If you have a very specific look in mind a photo example can be a great way to show your artist what you want! Just remember that Pinterest photos can be deceiving so keep your expectations realistic. And if you don’t have a photo, that’s totally fine.  

Your makeup artist wants to know your opinion, their goal is to make you look good, and for you to love how you look! There are so many different ways to do someone’s makeup that can look good, it’s ok if you prefer it a different way.

Definitely let them know everything you can beforehand if you have anything specific you don’t like (ie. ‘I don’t like how I look with X color on my eyes’) or that you feel like you need to be able to look like yourself (ie. ‘I always do winged eyeliner, and don’t feel like myself without it!’).

It’s also okay to not have any idea what you want, and be open for suggestions. If you’re feeling a little anxious, ask if you could see a mirror at some different stages of the process so you can make sure you like the direction it’s going. If there’s something that stands out it’s easier to change during the process rather than at the very end. Keep in mind though that sometimes you do need to wait for the final look to really see it—the lashes coming on at the end can be what ties everything together and makes you love love it! 

miscellany!

Feeling awkward?

The first few minutes are always a little awkward, don’t worry! I’m nervous before every engagement session so it’s normal if you are, too. If you drink alcohol, sometimes (aka oftentimes) I’ll suggest a shot at the start to get us all loosened up. It’s okay if you don’t know what to do at first, I’ll guide you and have you mirror some poses if you’re unsure. We’ll wander and photograph around the first location for up to an hour then change wardrobe (if you want to, no pressure either way) and head to the next location.

Pets, please?!

If you want to incorporate your pet into some photos, let’s do it! After lots of practice, unless you have the best behaved little furball baby, I’ve learned it’s best to do this at or near your home and to limit it to one location. From there we can have someone pick up your pet if we’re out, or we can swing back to your place and finish up at a location near there. Even the best behaved pets can derail our session, so we should always try to have a plan in place before starting to ensure things flow as smoothly as possible.

Don’t get hangry (or thirsty)

One of my best friends turns into a complete monster (she’s the first to admit it) when hungry, and you may be the same way. It’s a good idea to eat something (nothing too heavy; I only ever want to sleep after a giant bowl of pasta) beforehand so we can move through the shoot without having to stop to grab a bite. Unless, of course, you want to incorporate a meal into your session, which I’ve done lots of times! A little picnic or food truck or quick detour to an ice cream shop will always provide cute photos and natural interaction.

Limit the luggaage

Try not to bring a lot of extra stuff along as we’re shooting. We’re sometimes in a car and can leave non-valuables in there, but in busier cities we may be walking or relying on public transit which makes dragging extra bags a bit of a hindrance. I carry my gear pack and can tuck some of your smaller items (wallet, keys, phone, sunglasses, chapstick, etc) inside and could possibly sling a small bag over my shoulder if you need, but constantly putting down bags will distract us and kill the candid nature of the shoot.

DO YOU WANNA

know more?

You can find way more info in my handy dandy Wedding Planning Guide, or head over to my FAQ or About pages to learn all about me and my process. Ready to book your engagement session or learn more about my wedding packages? Tap through to my contact form below!

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