I was already post-college when The Upsides came out so I didn't quite have that same relationship with the band/albums, but I totally get it from having the same thing with earlier bands
I was a week away from turning 16 when Suburbia came out. They played Buffalo 3 times in 2011 in a matter of months and I think these shows really helped bring our friend group together. To this day, this band is the only headliner that can get all of us out to the show no matter what we have going on. Fun times! March: Headlined a skate park (RIP Xtreme Wheels) July: Warped Tour October: Support on the Pop Punk's Not Dead Tour
Surbubia works for pretty much any time you feel like you're taking a step backwards in life, but The Upsides is very college coded