You've just gotten engaged, you are on the moon, ecstatic to be celebrating with the love of your life... and absolutely inevitably, you are immediately bombarded with questions from everyone you've ever met. The "when & where are you getting married?" (about one hour after you've gotten engaged)... the numerous inquiries to your dream vendors... and then the engagement photos come along. When should you plan them? Where should you plan them? Should it be an activity? A location that's nostalgic to you? Or somewhere entirely new?

Decision fatigue is a real thing when it comes to planning weddings, especially, and planning for your engagement photos is no exception. It's too easy to get lost in the overwhelm of it all and let the engagement photos be just another task to cross off the list in your wedding planning binder - when in reality, they are an incredibly unique opportunity to craft an experience that not only leaves you with beautiful images, but tells your own story (and ideally turns into a super fun date night).

From a photographer's standpoint, I adore engagement sessions because it's the first time I really get to meet and connect with my couples. I include them for every wedding package so that we have a chance to get to know each other and how we work together before your wedding day - but from an artistic standpoint, it's such a special way to learn your story and find creative ways to commemorate this point in your journey together. They are chicken soup for the creative soul, but I know they can be an awkward and overwhelming aspect of planning for many couples. Some of the biggest things to consider, such as when and where and how to plan an engagement session, are things that we always tackle together.

When should you schedule your engagement session?

This depends entirely on what you want to use your photos for. Typically, save the dates are sent between 8-12 months before your wedding day - so if you would like to use the images for your save the dates, I would recommend scheduling your engagement photos 9-14 months before your wedding day. If you would prefer to use the images for just your formal invitations, I would recommend scheduling your engagement session for 6 months prior to your wedding day, at the latest, so you can send your formal invitations around the 4 month mark. Ultimately, I don't think "too early" exists - but these are some of the checkpoints to keep in mind.

To narrow down your selection even more, I encourage you to think about the seasonality of your vision. Do you want spring florals, or summer greens and wildflowers? Or are you more energized by the idea of autumn leaves, or even a snow flurry during your session? If any of these ideas leap out at you, it's worth scheduling your session with these factors in mind!

Below are a couple of unique seasonal features from a few of my past engagement sessions, from autumn foliage to a bonafide snow storm:

winter snowy engagement session by Pennsylvania wedding and elopement photographer Anna Claire Photos

Ashley & Joe's winter engagement session (Philadelphia, PA)

autumn mountains engagement session, by Pennsylvania wedding and elopement photographer Anna Claire Photos

Brit & Evan's autumn engagement session (Poconos, PA)

New Jersey blue hour beach engagement session by Pennsylvania wedding and elopement photographer Anna Claire Photos

Peyton & Gabi's summer blue hour engagement session (Spring Lake, NJ)

Engagement Session Ideas

Engagement sessions are a blast because we get to be so creative throughout the planning process and the session itself. The obvious priority is finding a beautiful and aesthetic location to serve as your backdrop, but we have a wonderful opportunity to incorporate elements of your story and your relationship that make your session truly unique.


Whether you are super, duper into board games, or maybe whiskey tasting, there are infinite ways to bring your favorite activities to your session, or even schedule your engagement session at a specific location. Here are some more ideas:

  • Bring your favorite board game or card game to any location we choose
  • Bring flights of your beverage of choice (whether that's coffee, or boozey... or maybe just plain tequila shots)
  • Go to your favorite distillery or winery
  • Hit the trails & take a hike at your favorite outdoorsy spot
  • Bring your four legged friends along for your favorite family activity
  • Go bowling at your favorite alley
  • Play video games (or go to your local arcade)
  • Visit a small town movie theater, for the film buffs
  • Go to a small town airport (most applicable to pilots)
  • Bring your paddle boards, rowboats, or other aquatic activity to your favorite water feature

The ideas here are truly endless, and we can get as funky as you want. I've had couples bring an antique car that's been in their family for years, and I've had couples bring a chess board to the beach. The sky is the limit.

blue hour antique car engagement session, by Pennsylvania wedding and elopement photographer Anna Claire Photos

Morgan & Tyler with her parents antique getaway car from their own wedding (Philadelphia, PA)

record player engagement session in Lake Placid in the Adirondacks, New York, by Pennsylvania wedding photographer

Emily & Nick with their favorite records (Lake Placid, NY)

fall engagement session with a dog, by Pennsylvania wedding and elopement photographer Anna Claire Photos

Sophia & Wyatt with their pup (Philadelphia, PA)


As fun as it is to involve some of your favorite or everyday things in your engagement session, we can also incorporate an entirely new experience for your photos. What are some things you've always wanted to do together? Take out that list of date ideas on your notes app and let's see what we can do. This is another area where we can get super, duper funky and creative. For a few ideas:

  • Getting a tattoo together
  • Going for a hike
  • Packing a picnic
  • Visiting a carnival or amusement park
  • Going to a new bar, cafe, or restaurant
  • Visiting a museum or art gallery
  • Doing something touristy in your own town or city
  • Taking a beach day
engagement photos at a marina in Boothbay Harbor, Maine, by Pennsylvania wedding and elopement photographer Anna Claire

Trisha & Lucas at a marina (Boothbay Harbor, Maine)

sunrise engagement photos at Acadia National Park, by Pennsylvania wedding and elopement photographer Anna Claire Photos

Kelsey & Cait at sunrise (Acadia National Park, Maine)


Whether we are returning to the place you got engaged or going to your family home, we can absolutely visit areas that have been meaningful to you throughout your relationship. I've spent time in family properties, hometowns, the location of your first date and first kiss, and even returned to the place where a couple secretly eloped months before. These places hold such a significant piece of your heart and of your story, and it's always incredibly special to return there for your session. Below are a few ideas of places we can visit:

  • Particularly special date locations (whether a first date, or just a favorite spot)
  • The place you met
  • Somewhere your parent(s) used to bring you
  • Grandparents house
  • Your hometown
  • Your own home or apartment
  • The place you got engaged
Engagement photos at Asbury Park, by Pennsylvania wedding and elopement photographer Anna Claire Photos

Francis & Chris in the town she grew up in (Asbury Park, NJ)

Engagement photos in a dive bar, by Pennsylvania wedding and elopement photographer Anna Claire Photos

Kate & Ted in the bar where they met (Philadelphia, PA)

Ultimately, there are so many ways to be creative for your engagement session that these lists barely scratch the surface. What I hope to leave you with is some encouragement and a spark to find what feels right to you - and most importantly, the most authentic and personalized way to tell your story.