Reading Time: 3 minutes

Stunning photography is supposed to look effortless. It’s not. Even the smallest details take meticulous planning. I’ve boiled down my 7+ years of experience with engagement shoots into these 6 tips for planning your engagement shoot. Enjoy – and post your questions in the comments below.


Your photos should express who you really are as a couple so it pays to have a vision you can share with your photographer. This is easier than you think.

The trick is to put two things you love together into a story. For example, if you told me you were an outdoorsy type who loves Game of Thrones I would suggest a romantic and very stylish photoshoot in the woods. On the other hand, if you are a fur-baby couple who loves cooking then I’d suggest a lifestyle photoshoot right in your home. Love urban adventure and architecture? Let’s explore downtown Chicago. Did you meet on the CTA during your morning commute? You get where I’m going right?

The important thing to remember is that the focus is on you and your relationship, not your surroundings so don’t get caught up in the perfect backdrop. Instead, focus on how those surrounding make you feel.

Cute young couple in a laundrymat
How and where did you two meet? Let’s use your story as part of your engagement shoot.


Putting some extra consideration into your outfits is a smart idea. Clothes don’t make the man or the woman but they do affect how we feel and of course how we look in-camera. There are color and pattern combinations that look great in the store but will make your photos look dated so definitely consult with your photographer before deciding. If hair and makeup are not your forte start your day at a trusted salon and don’t forget a manicure for both of you!

Happy couple with doggie in the snow
If you love your fur-baby to pieces be sure to bring them to the shoot!


We live such busy and distracted day-to-day lives it’s really a great idea to make your photo day a mini-vacation. This way you’ll feel connected and romantic as you head into the shoot. Planning a real date or activity to tailgate your photoshoot makes the day into an adventure. For example, if you love the Chicago Art Institute don’t stop after you get a few photos in front with the Lions. Go see the Andy Warhol exhibit inside get tickets to the Chicago Symphony Orchestra which is right across the street.

The grand staircase inside the Chicago Art Institute is one of many portrait-worthy spots inside the museum.

My VIP Couples List is The Bomb

Didn't join earlier? Enter now to get more useful insider tips and enter to win $400 worth of gorgeous fine art prints. Just click refresh to get that popup back now!


A good photographer can light you beautifully at any hour but if you want that romantic golden sunset feeling in your photos then schedule your photoshoot around that time. Noontime sun is the harshest because the sun is directly overhead and early morning light can also be magical. The important thing is to know beforehand which look you prefer.

Stylish couple playing on the beach
Late afternoon sun gives your photos that reddish glow. Is that the look you want? Be sure to discuss this and time it right.


Unless you’re an actor, model or a social media influencer with a million followers you probably aren’t 100% comfortable being photographed. The best way I’ve found to reduce that feeling of being camera-shy is to slow it down and get to know my couples as humans first. Sometimes this can be done by phone, sometimes coffee or even dinner together. It comes down to building some friendship and trust and you should expect that from your photographer.

The better your photographer knows you and your story, the more authentic and unique your photos will be.


With all the focus on digital everything these days it’s easy to forget to plan for some beautiful fine-art prints of your photos. You and your beloved are certainly worth being made into something real. From albums to wall art or even just a few 5×7 prints your photographer should have options that fit your budget and your aesthetic.

Young couple in the woods having a good time.
Imagine the two of you captured in one of Chicago’s gorgeous forest preserves on display in your living room.

Jake Miller

Photographer, printmaker, jiu jitsu hippie, pyromaniac, science nerd, obsessive personality, dog nut, no inner-monologue. I'm a recovered addict and my life is dedicated to preventing domestic violence. Almond cookies are my Kryptonite what's yours?