While Dan was working as a reporter at the East Bay Times in Oakland, he met Jillian's best friend, Malaika. She mentioned that she had a friend who was interested in learning more about meditation, one of Dan's passions. Jillian and Dan met for the first time at a coffee shop in the San Francisco's Mission District, and attended a meditation group together. Afterwards, they feasted on ice cream at Humphrey Slocombe.

Dan had moved out to the Bay Area with the intentions of moving back to his hometown of New Orleans in a year. Then he met Jillian. She was able to keep him in the City for several extra months but he knew he needed to get back. They decided to move Jillian and her two cats, Emma and Kali to the Big Easy with Dan. In August, Dan moved with Emma first, sending Jillian daily POL (Proof of life) photos of her. Jillian followed with Kali on October 8. They live near the Broadmoor District where Dan teaches Mindfulness-Based Stress Reduction and Jillian works at a fabric and sewing studio teaching New Orleanians how to sew.

Dan covertly found out Jillian's ring size and preference and made plans for a "vacation" to DeSoto State Park in Alabama. With the pearl wedding ring hidden in Dan's jacket pocket, the two embarked on a road trip, which ended at the park. It had been raining all day, so Dan took advantage of the clear skies to suggest a walk in the woods. His plan was to propose at a waterfall, but somehow he managed to miss his destination. While Dan was studiously examining the map, rain began to fall. Dan found an thick clump of trees where they would be partially shielded from the rain, got down on one knee and proposed. Jillian's initial reaction was to nervously laugh for about 30 seconds, before saying yes. On their way back to their cabin, they found the waterfall!