James and Ashley met when Ashley started working at Rosemont College in 2018, during that time they became good friends. Ashley would help with Connor and Chase when James came to Rosemont to do business. When the pandemic hit, James would check on Ashley often to make sure she was okay because she was alone in Philadelphia in her apartment. Their mutual friend Grace, always told Ashley that James liked her, but Ashley didn't believe her.

Fast forward to November 2022, James comes down to Baltimore for Ashley's birthday and a pizza date, soon after that Finn makes the trip to Maryland...the rest is history!