Someone who is simply terrible in/at love. They fall in love easily, are very open with their emotions, and can't seem to find the love of their life. They have a sense of honor, great valor, a deep sense of right and wrong, and are very romantical in the extreme. When they woo or court a person they always try to be the best they can be for the other. A Hopeless Romantic is someone who always has a wistful look in their eyes, is sad and shows it discreetly, or someone who always seems to be happy, but when they think no one is looking they drop the act and it is plain to see. These people are sad, lost, lonely souls.
That poor boy is A Hopeless Romantic.
Just look at him, see how he's always smiling? Look into his eyes and you'll see the truth. A Hopeless Romantic that's what he truly is.
All is fair in love and warfare. So what if he can't help that he prefers one over the other?