I like how JRPGs and VNs do it, where you have to spend enough time with the girl you want to form enough of a relationship to be able to ask her out on a date near the end of the game.
Sakura Wars series had the most immersive execution I can recall. It used timed dialogue choices to make you more immersed and make the visual novel gameplay an engaging rather than a passive experience. The player has a short window of opportunity to choose a dialogue option. If the timer runs out, the player character remains silent, and the person they are conversing with will react as such. Sometimes, if you remain silent a few times in a row, they will think you're giving them the silent treatment and get mad at you. Sometimes remaining silent is the right answer. Depends on the character you are talking to and the situation. You can't always pick the "nice" answer (some of the girls like Sumire, Orihime, or Subaru will think you are a pathetic or a wimpy kiss *** if you do and boss you around).
By the 2/3rd point of the game, you reach the point where you have to pick amongst the characters you have raised high enough likeability to ask out on a date. Because most dialogue options will not satisfy everyone and will rub some people the wrong way, it is impossible to have everyone eligible at the end.
In SW2, your romance from the prior game gets imported over.