Tim and Cassie’s magical Charleston Proposal at Middleton Place
The Octagonal Garden is one of my absolute favorite locations for a Charleston Proposal at Middleton Place. It’s like the Garden was made for a Proposal with the perfectly symmetrical aisle centered with what I call, The Wedding Tree! This magnificent Live Oak Tree is dripping with Spanish Moss with the perfect view overlooking the water!
Tim and Cassie planned a getaway to Charleston for Tim’s birthday. Their trip centered around a concert they had tickets to and decided to extend their stay to explore Charleston! Little did Cassie know, Tim had been working behind the scenes with me for a month to plan a perfect Charleston proposal!
As a Charleston Proposal Photographer, it’s always an honor when another photographer chooses your work! Tim has a natural eye for light and knew immediately that the Live Oak tree in the Octagonal Garden was the perfect spot for his proposal to Cassie! He fell in love with Middleton Place so much that he decided to book their whole weekend stay there at The Inn!
The funniest Proposal Cover Story Ever!
I always talk to my clients about having a good Cover Story, or the WHY for where you are going. The Cover Story was that I was a photographer waiting on a client that was apparently running late. When I saw Cassie and Tim in the Octagonal Garden, I asked if they wanted a picture together. Cassie kept saying, oh my goodness, that’s so kind! (This was the plan all along!) Since I had my “real camera” there anyways, I offered to take a few professional photos for them. I asked Cassie to turn towards the water and when she turned around, Tim was on one knee … with a ring!!!! When I say she didn’t see it coming … she.did.not.see.it.coming!!!!! (Just scroll down to see for yourself!!)
Proposal Surprise Part 2: Cassie’s Family
That’s right! Tim coordinated with Cassie’s parents as a second, epic surprise! I scouted the perfect location at Middleton for them to be tucked away, able to watch as the Proposal happened. After Cassie said YES!, we walked around for more photos. I took them to another garden area where her parents were waiting … and her reaction was again: priceless! She was so surprised!!!
Middleton Place has it all when it comes to a Charleston Proposal!
I love that Middleton Place was center stage for Tim and Cassie’s whole Charleston Proposal weekend! From staying at The Inn, to proposing in the Octagonal Garden, to brunch at the Restaurant … their day was magical! I love that Middleton Place will forever hold a place in their story and allows couples to really take in the beauty of this milestone day!
Cheers to Tim and Cassie and their absolutely perfect Charleston Proposal at Middleton Place!
If you’re looking for a Proposal Photographer for a Middleton Proposal at the Octagonal Garden, I would absolutely LOVE to talk more! Send me an email here!
Tim & Cassie
Charleston Proposal
Middleton Place, Octagonal Garden


































Creative Team:
Location: Middleton Place, Charleston, SC
Planning: Jen Keys Photography
Photography: Jen Keys Photography
Florals: Jen Keys Photography