Mine was probably when I relapsed towards religion at age 15-16 and joined my mom's conservative megachurch, naïvely thinking I can convince them to be less bigoted and more "christ-like" as well as accept science
All of my teenage years were cringe but at some point I changed my clothing style to be more like that one dude in class who took drugs, sprayed graffiti and was always in trouble. Because he once said to me I could draw pretty good.