Jessica & Jeffrey | Rollins College Engagement Session | Orlando Engagement Photographer

I knew Jessica back when I worked at Knights Circle while attending UCF, and I've always known that she and Jeffrey were absolutely head over heels for each other. This sweet couple have been dating for over 10 years (yes, a DECADE), so how exciting is it that they are finally ENGAGED!

Here's how the proposal went, according to Jessica:

Jeff and I went on a weekend trip to savannah with my parents. I had no idea he was planning on proposing. We got to Savannah and went on a haunted pub crawl the night we got there (we love spooky stuff). The next morning we woke up and went to breakfast at Collins quarter (my favorite). After breakfast we walked to Forsyth Park to look at the houses and to show my parents the fountain (also my favorite part of savannah). My mom made a comment about wanting a picture by the fountain so after taking a couple pictures of my parents together Jeff and I stood by the fountain for a picture. After a couple pictures Jeff asked if we could take one more. At that moment I looked at him with a “what the heck” look because he hates pictures, and that’s when I saw his hand in his pocket! At that moment I gave him the “no you’re not” face and I got a “oh yes I am face right back” after that he got on one knee in my favorite place in the world while my parents got to witness the whole thing. It was absolutely perfect and completely unexpected! I wouldn’t change a single detail!

I photographed their engagement session a few months ago in March, and I'm so excited to finally share their session with y'all! We aimed for a beautiful location, rich with history and beautiful architecture. Rollins College was the perfect setting for this engagement session. I can't wait for their wedding later this year at Casa Feliz!


Chantell Rae is a fine art photographer serving couples in Orlando, FL & Jacksonville, FL, & is also available to travel worldwide. She specializes in Weddings, Engagements, & Portraits.

Chantell Rae

Chantell Cruz Photography, 518 Jimbay Drive, Orange Park, FL, 32073, United States

Chantell Cruz is a fine art wedding & lifestyle photographer, dedicated in creating authentic & timeless photos for the romantic at heart. Her work emulates the soft & classic look of film.