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How to Make Your Engagement Photos Feel Like a Romantic Date

Hint: It’s not about the perfect pose. It’s about the feeling.

Romantic, natural engagement photo inside the Art Institute of Chicago inspired by a morning date

Let’s be honest: traditional engagement photos can sometimes feel a little… stiff. You’re in a pretty place, wearing outfits you spent a little too long debating over, trying to remember if you’re supposed to look at the camera or at each other. And while those photos can absolutely be beautiful, what I really love are engagement sessions that feel more like a romantic date than a photo shoot.

So how do you do that? How do you take a session that could easily feel posed and turn it into something that’s real and fun and actually you?

Here are a few ways to make your engagement photos feel natural and like a date you’ll actually want to remember:

1. Start with a vibe, not a Pinterest board.

Instead of thinking about poses or props or matching outfits, ask yourselves: “What do we love doing together?”


That might be walking your dog along the lakefront, grabbing coffee and donuts or doing a crossword puzzle together on a Sunday morning, visiting your favorite museum, dancing barefoot in your living room, or sipping cocktails at your favorite neighborhood spot. Whatever that thing is—lean into it. We can always make it beautiful. What makes it personal is what makes it magic.

2. Pick a meaningful location.

Yes, I love a good skyline view as much as the next Chicagoan, but sometimes the most meaningful places aren’t the “top 10 engagement spots” you’ll find on Google. Maybe it’s the cozy wine bar where you had your first date. Or the stretch of lakefront you walk every morning with your dog. Maybe it’s your own home—yes, we can absolutely shoot there and yes, it can be insanely gorgeous.

And if you’re dreaming a little bigger? I love when couples take me somewhere that’s already special to them. Maybe it’s watching the sunset in beautiful Sedona, Arizona, wandering the shores of Sleeping Bear Dunes in Northern Michigan, or strolling hand-in-hand down a Parisian street you fell in love on. Whether it’s a weekend getaway or the place where you got engaged—go where your love story already lives. I promise, that’s an amazing way to get candid engagement photos that feel true to you.

3. Plan something to do.

The best moments often happen in between the poses—while you’re laughing mid-sip, while you’re reaching for each other’s hand, while you’re just being. Adding a little activity gives us that space.

Some ideas:

  • Share a bottle of wine on a picnic blanket
  • Walk through your neighborhood, stopping at your go-to spots
  • Bring your dog and let them steal the show (seriously, I encourage it)
  • Bake something together in your kitchen
  • Rent a private boat on the Chicago River (or any local waterway with a view)
  • End your shoot at your favorite cocktail bar or dive for a nightcap

It doesn’t need to be grand—it just needs to be you.

4. Time it right.

There’s just something about that golden hour light—soft, warm, and cinematic—that makes everything look better. But beyond lighting, think about what time of day fits your vibe. Are you morning people who want to shoot while the city is still quiet and sleepy? Or would a just-after-sunset shoot that rolls into drinks feel more natural?

5. Dress like yourselves—just maybe elevated a tiny bit.

There’s no “right” outfit for engagement photos. The key is to wear something that feels like you, just with a little more intention. Think: what would you wear on a date night where you really wanted to impress each other, but still feel like yourselves? Don’t be afraid to bring a few outfit changes, or even go barefoot if it makes sense. I’ll help you make it all work.

6. Let go of the “perfect photo” idea.

The best photos are the ones where you forget the camera is even there. My job is to guide you just enough to make it feel effortless and natural. No need to practice poses in front of the mirror or worry if you’re doing it “right.” If you’re connected and present with each other, I promise that will shine through more than anything else.

Make it your own.

At the end of the day, engagement photos are less about documenting this one moment and more about capturing your dynamic—who you are together, right now. It’s like a little time capsule of your love story, told in the most natural, intimate and joyful way possible.

And if we can make it feel like a romantic date while we’re at it? Even better.

Thinking about your own session? Whether you’re planning something local in Chicago or dreaming up a destination session somewhere sentimental, I’d love to help you create something that’s meaningful, beautiful and yours. Reach out and let’s start planning. I’d love to help show you how to make your engagement photos feel natural and personal to you!