Hmm..
Early 80s - some kind of cheap 20" BMX, steel frame, coaster brake, passed down to my brothers, must have been tossed by my parents at some point
Late 80s - Sterling "MTB" which would really be a flat bar gravel bike today (Stolen from a locked room + locked rack when I was 18 freshman year of college)
2000 - Giant Iguana - Retired around 2005?
2000 - Trek 2200 - Cracked/fatigued chainstay in 2004
2004 - Trek 2300 - Warranty replacement, sold in 2007 when the Serotta was inbound
2004 - Giant TCR Composite - sold after the 2300 arrived
2005 - Giant NRS - retired in 2022
2005 - Some kind of no-name fixie, sold it after a year or so
2007 - Serotta Concours - sold to a friend in 2011
2011 - BH G4 - Wrecked in 2013 on a roof rack.
2013 - All City Space Horse - still in action but as a flat bar commuter right now, this might be the bike I've put the largest # of miles on
2016 - Trek Domane 5 series frameset - still in action
2022 - Trek Farley 7 - very much in use
General theme is I have mostly been a roadie but should have mostly been a mountain biker as I tend to get on a MTB and fit well and love it for a long time and road bikes somehow are more finicky and come and go and I'm never as happy.