Enjoying certain kind of games doesn't have to indicate the person is lacking something in real life; I like shooters and management sims but have zero interest in shooting or managing anything (except my own work) IRL. Similarly with dating simulators, for me it's more about enjoying the story, the characters and the writing. Hatoful Boyfriend was already mentioned and it's really great, I've also enjoyed Monster Prom a lot, it's more of a "party game" though.

I kinda wonder about the genre definition and what games should be called dating sims and which not. Like Crosmando said, there should be some simulation element to it so it's not just a visual novel romance story, but how much do you think? If it's a branching story where you are presented with choices and dialogue options that have to be correctly selected to progress relationships with certain characters, would that be enough?