5 Things To Consider When Planning For Your Engagement Session

Apr 22

Filed in: Engagement

You’re Engaged!

Let’s start with that. This is one of the coolest stages of your life and I want you to soak every single second in of it! YES – there’s a lot to do before the wedding (or maybe you’re eloping in Thailand) but there’s so much joy to experience.  One of those joys – engagement photos! 

Engagement photos are hands down my absolute favorite thing to shoot (besides dogs, I’m sorry but dogs always win).  I love the giddiness and excitement and getting to learn about a couple’s love story and their quirks between each other. I love watching couples go from nervous to feeling like they’re on the best date they’ve had in months.

Engagement sessions can also be a bit overwhelming to some so I put together a list of 5 things to consider when planning your engagement session.

Engagement Couple at Garfield Park Conservatory

1. Location Location Location

Think about areas that are meaningful to your relationship. Maybe it’s the bar you met at on your first Tinder date, or the park where your man proposed.  Maybe you like to run together on the lakefront in the Summer, or spend time together at Target! Think about places that feel natural to your relationship and you feel comfortable in.

Couple at sunset in Chicago


I’m probably the most comfortable when I’m in a pair of leggings, hair in a messy bun, dog at my side, curled up on the couch with my husband (most likely watching a true crime documentary).  If home is where your hearts are, do your session there! I’ve found that in-home sessions take some of the stress of having your photo taken in public off.  I’ve also found that people loosen up and are more comfortable faster at home – which makes perfect sense.  The other part of in home sessions I adore, is being able to capture tangible things at that stage in your relationship. Things you can look back on later in life and say “Oh honey remember when we had that mustard yellow couch when we were engaged!”  Not only are we capturing YOU but we get to capture your home together too!Cozy couple at in home engagement session

2. Timing

When Do I Schedule My Session?

I recommend having engagement photos done 6-9 months before your wedding date so you can use your images for fun things like save the dates, your guestbook, and even wedding decor. And of course, for a bangin’ new profile picture.

Winter, Spring, Summer or Fall

Think about what season it will be during that time frame and if it fits your personality and relationship. If you hate snow, you probably don’t want to do your photos in January in Chicago. If you’re super stressed out about sweating during your session maybe Fall is more your jam.

Chicago couple at sunrise for engagement session

The Day Of

Being a lover of natural light, my timing for your session isn’t a coincidence, it is scheduled so that we have the best lighting for your photos whether that’s natural light streaming in through your windows or a gorgeous sunset.  Make sure you allow enough time for travel // traffic // parking. If we’re meeting in a busy location, check out SpotHero. This is my go-to tool when I know I’m doing a session in the city.  You can find a spot or garage near our location, and book it ahead of time!

Couple in downtown Chicago in snow

3. Clothing!

I did a whole post about what to wear for your engagement session here, but wanted to add in a few tips here as well! I love to offer the opportunity for an outfit change halfway through a session. This gives my couples the opportunity to get a few different looks and feels with their session while maximizing our time together. Many couples opt for one dressier option and one more casual option. Depending on where we are shooting – a quick change in a car, behind a bush, or a public restroom is sometimes the norm. I’ve become very talented at towel holding, so have no fear, I’ve got your back (and will make sure your back end is covered!).

Chicago couple under string lights


4. Props, Popping Champs & Puppies

If you’re wondering about how you can make your experience personal and memorable, bring along any props that are special to you. Your session should scream YOU, so if that means bringing your four legged friend along (OMG YES PLEASE DO THIS) or props that tell your story, please do! I love incorporating props into photos in a fun way! Maybe it’s something from your proposal or a hobby you both love and share, maybe it’s a food you love or a bottle of champagne (this is always my own photoshoot go to!) that is special. Whatever you want in your photos, I’ll do my best to make it happen!

Couple drinking champagne on Chicago lakefront

5. Nerves

It’s more than okay to feel nervous! Please know that I do not expect my clients to be models (although hot damn, most of you could be!). My job is to direct my couples in a way that helps them relax, feel natural, and be their true comfortable selves in front of my lens. I always tell them they don’t need to practice poses, study Pinterest pins or let the nerves take over. If you are nervous, it’s totally ok – I promise the end results of our time together will be something you love. So leave those nerves at home and get ready for the time of your life!


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