For me, i started with an iPad Air first
iPad Air (2021) as just wanted a established tablet brand while holding on to my Pixel Phone
iPhone 15 Pro Max ( Oct 2023)
Apple Watch (Oct 2023)
Apple Airpods Pro 2 ( Nov 2023)
Apple TV 4K 3rd Gen ( Nov 2023)
Probably will get a macbook air late next year
iPhone 6 Plus (August 2014)
Apple Watch Series 0 (October 2015)
MacBook (July 2016)
iPad (circa 2017)
AirPods (February 2017)
Apple Card (August 2019)
So I guess August 2019 lol