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I guess. I mean, Lue has a girl he favors in this game, and it's kind of a shitty thing to do to your broship, but you can pursue her as well. No spoilers!

From what perspective? If you want the MC to be the "town stud", "banging" all the girls, there are some story line branches that make it somewhat possible (but not in all cases -- only certain characters and branches). If you want to target Ashley, knowing Luis is crushing on her, and do dirty things with her "behind his back", then yes, there are some scenes where this can happen.