i dont really get how the dates work, am I missing clues i'm supposed to pick up on, stuck on the first one
As mentioned, the text message about character's action should give a hint on what to do next. If someone says something about themselves, they expect you to ask more questions; if someone gets closer, they may expect a physical contact, and so on.
In setting, you can increase the number of mistakes you can make during the date, to make dating easier. Or you can use cheats to skips dates altogether if you don't like those.