The fine line between sensitive and "just friends"/wussy?

A bit of distance. Women don't expect men to be totally empathic, just a bit sympathetic. Women also assume any man who allows a woman to make the relationship all about her emotional state has no emotional needs of his own. Because women expect men to be a LEETLE bit assertive. Not aggressive or asinine but assertive. If you never assert your needs, then clearly you don't have any worth worrying about. If you come back later with the "but I've been in love with you all along!" (translation: "I wanted to bone you but figured I'd have a better chance if I deceived you and pretended I didn't want to bone you") - dude if you "loved" me all along then why didn't you say something? Because you're a liar or because you're too wimpy to speak up? Either one is bad. Avoid those pitfalls.