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I will agree with you Chris that doomed or tragic romance is often more touching and dramatic than 'happily ever after' kind. However do note that this kind of ending, often leaves many viewers feeling unsatisfied with the conclusion. That is why they resort to writing fan fictions or venting at you for breaking their hearts. So an alternative would be giving the players a choice to experience both kind of endings in the game. One tragic, the other a satisfying kind. An example of such game? Your very own Knights of the Old Republic 2's Atton Rand with his several possible conclusive outcomes. Another thing I feel is that, romance is should never be declared openly or blatantly between the characters. Like you mentioned, it works best by dropping hints or occasional exchanges in flirting. Also I thought that Obsidian could use the PC's attributes to provide players with bonus influence points with certain opposite NPCs based on their first encounter and impressions. For instance some women enjoy men with muscular body(strength check). Some prefer intelligent/wise characters(Intelligence/Wisdom check) while others simply like good looking ones(Charisma check)