Jenna met Bosley before JT (which was probably true for a lot of people who entered the Bailey house) during a college football weekend at MSU in 2009. Fast forward to a few years down the road and the two of them crossed paths through St. Clair boat weekends, Dane-Stock, weddings and tailgates. Jenna moved to Portland, OR and JT moved to Brooklyn, NY.

The two bonded over working in healthcare during the COVID-19 pandemic. Once both back in the Detroit area, these casual run-ins became more frequent and intentional. Matching Tiger King Halloween Costumes and "to-go" cocktails at Sugarhouse turned into more serious talks about their mutual love for their dogs and the outdoors, travel, and Taylor Swift. They "officially" started dating in February of 2021 when JT romantically and matter of fact said to Jenna "I told everyone at work that you're my girlfriend, so.....?" JT had accepted a job in Northern, MI and the conversations turned more serious.

By the end of 2021, the family of four (JT, Jenna, Sport, and Buddy) would officially call Petoskey their home. They have continued to fall more in love with northern Michigan and each other and look forward to celebrating with everyone in September.