Josh and Ali are both graduates of Thomas Jefferson High School. They reunited years after graduating when Josh reached out to ask Ali if she would join him for a cocktail. Due to COVID, their first date entailed driving around town in Josh's car because everything was closed. It didn't matter because the two had a lot to catch up on!

After college, Ali spent time traveling to different states for a masters degree and work. She eventually made her way back to Pittsburgh where she found a permanent job. Meanwhile, Josh graduated from 2 police academies, worked in 3 different counties, and then also came back to Pittsburgh to work a permanent job.

The unexpected relationship became more serious when the couple started falling in love during a family reunion trip in Tennessee.