Winston is hot headed, insecure, shy and a hopeless romantic. Or, at least, he's helpless with falling in love. With the wrong people. All the time. He vigorously dislikes himself, and has a tendency to interpret kindness or comradery with romantic feelings and sets himself up to self destruct. He's vaguely aware of this, and tries to hide behind bristled hostility, but he's not very good at it. He's easy to fluster and he's kind of a shitty friend, who'd really rather wallow in his self pity than rise to the occasion. Learning to not be an asshole and to respect and accept himself is the path he needs to get on, but he's set his heart against change for the fear of it.