According to Jon:
The proposal was difficult for me to plan because of how good a detective/intuitive Jalisa is when is comes to me trying to surprise her.
If there were an Academy Award for acting the part of nonchalant/slightly bored boyfriend during this process then this guy would have won *points to self*.
I told Jalisa that the proposal would be at least a year away, but I knew we had holiday pictures planned for the end of October. I ordered a custom ring from California and the shipping was delayed until just days before I planned to propose.
On the day of the proposal, I reached out to our photographer to let her know what I was planning. She did a great job with keeping the secret and helped me plan how she was going to pose us so that I could spring the proposal on Jalisa. I was so nervous on the ride to the location for the pictures because the ring box was obnoxiously large and I had no place to hide it. I was fortunate to have Jalisa fully engrossed in planning the different poses that she didn't see the ring box shoved into my front pocket. We got to the location and our photographer asked us to get ready to pose for the pictures. I distinctly remember Jalisa not wanting to get into the pose we had come up with so that I could propose. I pretty much barked at Jalisa to get into the pose as everything had gone smoothly until that point. She was a good sport and didn't get too mad at me for my insistence on striking the pose. I pulled the ring out and the rest is history. I couldn't have asked for a better day and the photos were perfect.