Tiff and Darryl met online during the summer of 2014. Darryl asked Tiff on a date shortly after but Tiff played hard to get and initially said no. After a few more weeks of talking and convincing from Darryl, they finally met up for their first date on August 9, 2014.

Fast forward four years later, it was the Saturday before Tiff's birthday and she believed that Darryl left the day before to go on a business trip. Little did she know, Darryl was still in town and he arranged for Tiff's cousin Jenny, to take Tiff out to get lunch and to get her nails done "for her birthday." After they finished at the nail salon, Jenny got a call from her boyfriend saying that he was having car problems and asked if she could pick him up from Palos Verdes. Tiff went with Jenny and when they got there, Tiff saw Darryl standing under a gazebo with flowers and a "Will you marry me?" puzzle.