In person: 2008 at USC. I live in Arizona and decided to go out to the Coliseum to see the Buckeyes in person. I went to college in Orange County from 2002 to 2006 and hated USC fans at the time but despite the humiliating Buckeyes loss, had a newfound respect for Trojans fans (almost everyone I encountered was smart and knowledgeable without being condescending), and the Coliseum, while not Ohio Stadium, is a pretty neat place with a lot of history.
Went to the 2009 Fiesta Bowl versus Texas and after that just assumed I was cursed whenever I watched the Buckeyes play in person. Needless to say, I was very nervous attending the 2014 Cincinnati game at the Shoe, but we all know how that turned out.
TV: 2009 hosting USC at the Shoe. I was skeptical of Tresselball leading up to that game, but that was the moment I lost all faith in his ability to beat anyone worth a damn, and I hate saying that because I love and respect the hell out of him as a person. I was texting a friend of mine who was a USC fan while we watched the game on TV and when we went ahead before blowing the lead I'm pretty sure I told her at one point something to the extent of "alright, how are we going to give this one away?"