Hey there, as from the title you are either getting two hints. One is that by cheating the game to get what you want, yada, yada, yada. However, that is not what I am meaning for this.
I believe at one point your girlfriend could cheat on you, depending on the other male characters interested in her and how loyal she is. That straight up just says what I have to say.
Another thing I think will make the game more interesting, say there is a damsel in distress, you could go help her (Be it she is being harassed or guys are annoying her) when you go and help her, it gives a larger boost for them to like you.
I feel very strongly about these two as I feel as though it adds a lot more realism into the game. Anyway give me your ideas as well as I'm happy to hear them
I really dislike this idea of cheating, even it happens in the real life....
So, the theme of the "damsel in distress" can be really cool!
Imagine, late in the game (I'll go on the way your roommate is Brendan), May/Leaf is kidnapped by a mysterious gang (Team Rocket, or Team -insert new name for Kobukan region's new evil organisation-), and they wanted your Charizard (or something else). You go with Brendan, Leaf/May (or just Brendan if the two girls are kidnapped) to rescues her(s).
So, in theme of kidnapping we can imagine the kidnappers are Team Rocket (from the anime) and they confuse you with Ash to take Pikachu (good time to implement anime characters).
In last, Leaf can have so mysterious relation with very bad guys and they want to take when you are in free time in Kobukan City, and you must rescue her, so many possibilities to implement the second idea in the game...