Let’s just call it out: having a camera follow you around can feel weird. Like, “what do I do with my hands?” kind of weird. But here’s the thing—engagement photos aren’t about being perfect, they’re about being you. Imperfect, sometimes fidgety, adorably giggly, and always real. That’s where the magic is. If you’re wondering how to feel comfortable in engagement photos, I’ve got you. Unlike the paparazzi, I’m not there for sneak attacks. I’m there as a friend (who happens to be a professional photographer) to make sure you get the photos you deserve from this milestone chapter in your lives.
If you’re anything like Sophie and Jack (and honestly, most of my couples), the idea of “posing” for photos is up there with public speaking and parallel parking. (Are you frantically Googling “engagement photo poses”??) I assure you there’s no need! The camera can actually become a third wheel on the best date night ever. You just have to find your groove, together.
Here’s how to feel comfortable in engagement photos, quirks and all.
Embrace the Awkward First Five Minutes
There’s this myth that some people are just “naturally photogenic” and everyone else is doomed to awkward, forced smiles forever. Here’s the truth: those first five minutes are rarely anyone’s highlight reel.
Awkward is just the dress rehearsal for comfortable. If you’re worried about your nervous laugh or the way you always blink at the wrong time, congratulations, you’re completely normal. And it’s the first step in my guide on “how to feel comfortable in engagement photos.”
When I met Sophie and Jack for their downtown Chicago engagement session, I could practically see the “what do we do now?” floating above their heads. I assured them (as I do every couple) that it’s normal to need a few minutes to shake off jitters. But after that, it should just feel like a really good date. Sure enough, these two leaned into their connection with no trouble at all. It wasn’t hard to catch them candidly smiling, playing, and showing off the chemistry that brought them together in the first place.
My tip? Don’t fight the jitters. Let ‘em in, and laugh about them. Then, have fun as they melt away.
Engagement Sessions Build Confidence Before Wedding Day
Engagement sessions are my secret trick. Not just for taking great photos (though yes, there will be plenty). They’re about us getting acquainted in real life, shaking off those “what do I do with my hands” nerves before you’re dressed to the nines on your wedding day. We figure out what feels natural, what makes you both laugh until your ribs ache, and which side is your “good side” (spoiler: they both are).
By the time the wedding arrives, we’re not strangers anymore. We’ve stomped through puddles together and survived the wind turning your hair into modern art. Trust me, it shows. Authentic engagement photography only works when there’s trust and a little vulnerability.
Make It a Date, Not a Photo Shoot
The best candid engagement photos happen when you forget you’re being photographed. More than anything, I don’t want you to feel scrutinized or like you have a camera in your face all session long. Instead, I’ll gently guide you as a friend and help you discover your confidence. (You might be surprised by your innate modeling skills.)
With Sophie and Jack, we started at the Board of Trade Building—beautifully iconic, a little dramatic, and very Chicago. The city was buzzing, the light was moody, and the world felt big and small at the same time. As we wandered, chatted, and people-watched, I encouraged them to lean into whatever felt like them. Sometimes that meant a romantic dip on the crosswalk (safely! I’m fun, not reckless), sometimes it was a silly wraparound hug that made them dissolve into giggles.
Pro tip: bring something that feels like home. A favorite jacket. A playlist that makes you both dance in the car. Or just that inside joke you always go back to when you want to remember why you fell for each other. Have some funny or surprising stories? Share them with me! I’d love to hear them, and it’ll help you relax, too.
Don’t Aim for Perfect; Aim for Real Moments
Perfection is overrated. The real heart-melters are the photos where hair gets caught in the wind, your foreheads bump together, or you both crack up because you almost tripped over a sidewalk crack. And I want you to genuinely have fun during your session.
Sophie and Jack’s Chicago engagement session was full of these moments. The city lights, the swoosh of cars, the “L” trains rumbling overhead. At one point, they stopped for wine along the Chicago Riverwalk, and even the photos of them standing in line are precious because they’re so them.
Let the mess be part of it. Let the city be loud, let your dress blow in the breeze, and let yourself be a little ridiculous. These are the photos that feel like you when you look back years from now, and you’ll be so glad you embraced those in-between moments that hold gold-mine memories. It’s fun to remember how you were “back then.”
Trust Your Photographer (and Yourself)
Here’s an unspoken part of my job: to make you forget the camera is even there. I’ll guide you, prompt you (“Whisper your favorite pizza topping in their ear in your best Batman voice”—real prompt, real results), and make sure you look like yourselves on your best day.
But the best thing you can do? Trust yourself. Trust that your connection is enough, that you don’t have to perform or be anything other than the two people who decided to do this wild, wonderful thing called life together.
Sophie and Jack showed up a little nervous, but left glowing—and not just from the city lights bouncing off the skyscrapers. They left knowing that the camera saw the same thing I did: two people who love each other deeply and enjoy each other’s friendship.
What Matters Most in Your Engagement Photos
At the end of the day, it’s not about the skyline, trendy poses, the sunset, or even the perfect outfit. It’s about how you feel with each other—comfortable, safe, seen. If you can be yourselves, my camera and I will take care of the rest.
If you’re looking for a Chicago engagement photographer who captures real, candid moments, let’s create photos that feel like you.
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