Why are you telling me this? (S2 E9, "Run Away Little Boy")

'O Romeo, Romeo! wherefore art thou Romeo' ...he's headed to military school. We are discussing Tristan's swan song as Romeo. Chad Michael Murray's last Gilmore Appearance in Run Away Little Boy. The debate: Is Tristan the Villain? Is he just misunderstood and misguided? Does Rory have feelings for Tristan?