Gwen and Tanner met at a training for Deloitte at Deloitte Univeristy, which Bloomberg infamously called the Disneyworld of the professional services world. Both of them were not looking forward to this trip due to the long and boring training sessions, but this all changed quickly when Tanner introduced himself. He secretly got the details about Gwen and realized they likely had a good friend in common (Colin Francesco) and he immediately used that connection to start talking to her. For the rest of the trip, they spent their nights at "The Barn" drinking beer and laughing at stories of Colin.

After training ended, they each visited each other a few times before they decided to have a go at long-distance dating. That lasted for 4 months at which point Gwen decided to transfer to the Chicago office for work related reasons (even though it was really to be closer to Tanner). They lasted a week on the same floor before Tanner decided to leave Deloitte for a new career with The Alinea Group.

Tanner proposed to Gwen while on a trip to San Francisco and Napa Valley in June 2017. He secretly reserved a helicopter tour of the Golden Gate bridge that was going to drive them up to Napa Valley afterwards. While the helicopter hovered over the bridge, Tanner unbuckled his seat belt and got down on one knee and the rest is history!