Karissa & Michael’s Creative Engagement Session

Karissa and Michael standing in front of the courthouse at their creative engagement session.
Karissa and Michael smiling in front of the courthouse at their engagement session.
Karissa displaying her engagement ring.

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A Playful, Personality-Filled Session From Downtown to the Quarry

Karissa and Michael’s engagement session is the perfect example of how creative engagement photos don’t have to feel forced or overly curated. These two started the session a little shy and reserved, but by the end, they were laughing, moving freely, and fully relaxing into the moment.

We planned their session while I was traveling through Eastern South Dakota the day before a wedding. Even though Minnesota isn’t a place I typically work, I didn’t want them to miss out on the engagement experience included in their wedding collection. So we made it happen, and it was absolutely worth the extra drive.

Karissa and Michael standing forehead to forehead in front of an old theatre in downtown St. Cloud.
Karissa and Michael in front of the Paramount Center for Arts in St Cloud.
Michael smiling at Karissa in front of a theatre at their creative engagement session.

Meet Karissa and Michael

Karissa and Michael are grounded, thoughtful, and easy to be around. In the beginning, they were a bit nervous, but as soon as we started exploring different spots and leaning into movement, the nerves faded. By the end, they were fully themselves.

They also brought their two sweet dogs, originally adopted from a reservation in New Mexico. Not only were they incredibly photogenic, but they knew fun tricks and added so much personality to the experience.

A couple spinning in front of the Paramount Center for the Arts.
Michael smiling at Karissa.
A couple kissing in front of a lighted theatre sign.

Multiple Downtown Spots for Variety and Texture

We started in downtown St. Cloud and wandered through a handful of fun, visually interesting locations:

Karissa’s blue-and-white floral dress was a beautiful contrast to the buildings. Color can bring life to an urban setting, especially one filled with neutral buildings and shaded textures. Her outfit added depth and interest without ever overwhelming the scene.

A couple sitting on the stairs at a courthouse.
Michael kisses Karissa's forehead.
Karissa and Michael kissing in front of St. Mary's Cathedral.

Tips for Urban Engagement Photos

  • Don’t shy away from color in neutral downtown locations
  • Consider dressing up slightly for an editorial look
  • Wear comfortable shoes for walking between spots
  • Keep things light, interactive, and movement-oriented (this is your photographer’s job)
Michael spins Karissa in front of the St. Cloud courthouse at their creative engagement session.
Karissa wraps her arms around Michael's shoulders, displaying her engagement ring.
Michael wraps his arms around Karissa, showing off the fun back of her dress.
Michael and Karissa standing forehead to forehead in front of The Regency Venue.
Michael's dog, Mack, jumps in front of the Regency Venue.
Karissa's dog, Remmy, shakes her paw in front of The Regency.
Karissa and Michael stand in front of the Regency with their dogs.

Into the Woods for Soft, Glowing Quarry Light

After exploring downtown, we drove to the rock quarry, which required a small entrance fee. From what we could find (or rather couldn’t), permits weren’t necessary, and Karissa joked she had connections since she’s an attorney and Michael is a police investigator.

Although it was golden hour, the quarry is tucked beneath the trees, which gave us soft, even light instead of direct sunlight. This kind of gentle, shaded glow is incredibly flattering and creates a timeless feel.

We stayed until the very end of blue hour, taking advantage of every lighting shift.

Karissa and Michael kissing at the Quarry.
Michael spins Karissa on a wooden bridge.
Karissa spins Michael on a bridge at the Quarry during their creative engagement session.

Why Photographer Lighting Knowledge Matters

In wooded spaces like the quarry, it’s easy to get heavy green color casts if you don’t know how to correct them. And once the sun disappears, the light drops fast.

Knowing how to work with natural light, avoid difficult color issues, and transition confidently into flash is essential. Without that experience, couples miss out on late-evening magic that deserves to be captured well.

Karissa and Michael kiss on a wooden boardwalk.
Karissa and Michael walk their dogs on a wood bridge.
Karissa and Michael kiss on the wood bridge.
Karissa and Michael smile at each other.
Michael spins Karissa.
Karissa and Michael smile at the camera.

The Mastermind-Inspired Engagement Session Finale

This was the moment Michael didn’t know he’d been waiting for.

As blue hour settled in, Karissa surprised him with jorts so they could recreate the Mastermind engagement photo scene from the movie. Michael was giddy as he showed us the clip on his phone on the walk back to the parking lot, and once we started shooting, the whole energy shifted.

I pulled out direct flash to match the edgy, stylized feel of the scene. Suddenly the session felt cinematic, creative, and wildly fun. These are some of the most unique engagement photos I’ve created, and they perfectly captured the playful side of their relationship.

If you haven’t seen Mastermind before, here’s the clip he was referencing.

Karissa and Michael having fun with some Mastermind inspired engagement pictures.
Michael has Karissa in a wheelbarrow position.
Karrisa and Michael sitting face to face during their goofy engagement session.

Why Direct Flash Can Elevate Your Creative Engagement Photos

Flash isn’t just a backup tool. When used intentionally, it adds:

  • an editorial, crisp punch
  • nostalgic film-like tones
  • a dramatic, cinematic edge

It’s a great reminder that having a photographer who understands all lighting situations matters. Otherwise, these moments never get captured with the energy they deserve.

Karissa lays on Michael during their funny, Mastermind inspired engagement photos.
Mastermind inspired engagement photos.
Karissa sits on Michael's back during their creative engagement photos.

A Session Worth Every Mile

Even though Minnesota isn’t a state I typically shoot in, creating this session with Karissa and Michael made the long travel day more than worth it. Engagement sessions build comfort and connection before the wedding day, which helps couples relax and enjoy their experience so much more.

Getting to meet them in person, watch them open up, and create something that felt fully true to them made this entire experience unforgettable.

Michael stands over Karissa during their Mastermind inspired section of their engagement photos.
Karissa and Michael sitting forehead to forehead.
Michael posing in his jorts and fanny pack with his curly hair.

Inspired to Plan Your Own Creative Engagement Photos?

Whether you want something playful, romantic, editorial, or completely outside the box, your engagement session is an opportunity to tell your story in a way that fits who you are.

If you’re dreaming up a session like this, I’d love to help you bring it to life. Reach out, and we’ll make it happen!

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About Charity Dowell

Black Hills Photographer

I’m a Rapid City-based wedding and portrait photographer capturing love stories throughout the Black Hills and beyond. My work blends an intentional eye with a heart rooted in Christ — always seeking beauty in stillness, meaning in the in-between, and honesty in every frame. I believe marriage is sacred, and your story deserves to be told with grace, care, and a touch of poetry.

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