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When to Schedule Engagement Photos

As soon as you log into a popular wedding planning site like WeddingWire or The Knot, you’re presented with a “wedding planning checklist” filled with every possible wedding-related task under the sun. Many of them may not apply to your celebration plans and situation! Something every wedding planning checklist will prompt you to do is to plan your engagement session.

While most couples will agree that they’d like to have engagement photos taken, they find themselves wondering when to schedule engagement photos around all of the other tasks that go into planning a wedding — not to mention keeping up with their daily lives and work commitments, too!

In today’s article, we’ll explore several options for when to schedule engagement photos so you can make an informed choice and book an engagement session that’s a perfect fit for the two of you.

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When to Schedule Engagement Photos

When will you need to use them?

When a new couple reaches out to me about scheduling an engagement session, this is the first question I ask, each and every time. If you’re planning to use your engagement photos for printed save-the-dates or invitations, then you’ll need to book, plan, and execute your engagement session with enough lead time before the wedding so you can use the images as intended.

As a general rule, if you want to be able to use your engagement images for save-the-dates or your wedding website, then you should plan on booking your session no less than 6-8 months before the wedding day.

Based on Theme or Season

Are you wondering when to schedule engagement photos so your session lines up with a specific time of the year? Want to know how to sync up your couples session with some beautiful fall color?

While weather patterns vary from month-to-month and from year-to-year, here are some general guidelines to consider (and please note — these guidelines are based around the seasons here in Chicagoland; if you’re planning a destination engagement session, timing may differ):


If spring blooms are a priority for your session, then May is your best bet for plenty of color. The ground will be warm enough for most flowers to be putting out buds, and the grass and trees will have greened up as well. Some flowers like tulips and daffodils bloom earlier (sometimes as early as late March) and flowering trees may bud as early as mid or late April.

Claire Isaac Engagement Session Lincoln Park Chicago 2021 74


Ah, golden summer engagement sessions. These are my personal favorite, because there’s no substitute for that warm light you can only get from a summer sunset in Chicago. While you can plan a summery session anytime between late May and early September, I’d recommend planning on a June session, as the summer heat and humidity are usually a bit more forgiving earlier in the season when compared to temperatures in July and August.

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For maximum fall color plan your engagement session for late September through October. It’s often best to work with your photographer to monitor the location you want to shoot at and adjust your session time as the trees begin turning colors.

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My snow-loving clients tend to like to do their winter engagement sessions in December or January. Our experience here in Chicagoland has always been that February is the coldest month of the winter, and no one (including the photographer!) wants to do a photoshoot when the thermometer is reading in the negatives.

One added caveat here: If you’re considering a December engagement session, double check what sorts of holiday decorations might be present at your shoot location. If you want an engagement session that’s merry and bright, this can be an added bonus, but if not, it’s something to be aware of and plan around.

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When in doubt…

If you’re not sure when to schedule engagement photos, ask your wedding photographer! He or she will be able guide you to options that work best for your needs and timeline.


Now that you know when to schedule engagement photos based on when you’ll use them and how to plan around seasons and weather, your next step to consider is making your engagement session personal and unique to the two of you! For more engagement resources, check out my article on “How to Personalize Engagement Photos” to make your engagement session special and memorable.