[Death by Mirrors]

Seriously though. General Smooch Quest strategy, aka the item hunter's guide to romance. Not very romantic, so I'll put it in a spoiler tag for those who rather want to try the regular way.

1) Remember what options you pick. Write them down if you tend to forget such things quickly. This prevents you from running into the wrong lane over and over again.
2) Pay attention to your date's facial expression. They all have a bad, neutral and good face, which will give you a hint to how well your last answer went with them.
3) On your next playthrough, if you're going for the main prize, avoid bad answers. You don't need to give all good, but the more good answers you score, the higher your chance to win someone's heart. Remember that one or more characters do in fact have instant game over answers in their dialogues, and avoid those too once you identified them.