There are some sessions that remind me exactly why I love my job, and Jillian and Jack’s fall Overlook Park engagement session was one of them. From start to finish, these two felt like family, and it was such an honor to capture their love story.

A Love Story Meant to Be

Jillian and Jack’s story began in a daycare center at an area club where they both worked. At first, they were just friends, so much so that Jillian actually set Jack up on a date with one of her friends! After a night of Chick-fil-A and a little matchmaking message relayed through Jillian, it seemed like nothing more would come of it. But months later, during one of Jillian’s college math classes, Jack texted her out of the blue. That single message turned into a first date, and from that day on, they’ve been inseparable.

Jack later proposed in the most thoughtful way. A sunrise picnic on the beach during a trip to Charleston. With donuts, mimosas, and the ocean as their backdrop, he positioned them perfectly for a hidden photographer before asking Jillian to marry him.

Sunset at Overlook Park

For their engagement session, we had the dreamiest fall evening. Overlook Park is one of my favorite locations for sessions because it offers such variety: open fields, walking paths, and stunning sunsets – and this night it delivered it all. Jillian and Jack laughed their way through piggyback rides, playful hip bumps, and so many little in-between moments that showed their sweet and fun connection. I literally yelled “ideal couple!” halfway through the session because it truly felt like everything was perfect.

A Family Legacy

What made this session even more special was the fact that Jillian is the third sister in her family I’ve had the honor of photographing. Her family holds such a special place in my heart. I photographed two of her sisters, who are triplets, and now walking through this milestone with Jillian and Jack feels like continuing a beautiful legacy of trust and connection. It’s rare and so meaningful to be welcomed into such important moments by the same family again and again.

Looking Ahead

Jillian and Jack love playing pickleball, taking walks, binge-watching shows, and spending time at the beach. They’re relaxed, adventurous, and completely in tune with each other which made capturing their session such a joy. I can’t wait to celebrate their wedding day and add another beautiful chapter to this family’s story.

This fall Overlook Park engagement session was cozy, playful, and full of laughter, and it reminded me yet again how lucky I am to do what I do.

XOXO ~ Heather Marie

More HMP Engagement Sessions:

Fall Hibernia Park Engagement Session | Madison & Zackery
Historic Poole Forge Summer Engagement Session | Rebecca & Christopher