I've tried this several times, on Easy, Medium and Hard, and can never get further than a second date. The dialogue choices are nothing like the way I would ever speak IRL. Some of the "good guy" dialogue is overly solicitous, passive and formal, but the "bad boy" route is just cheesy as fuck, a parody of what a 12-year-old thinks is manly talk. Regardless, I get shot down if I attempt either path. To make it worse, if you try to choose a middle route and converse normally, the character then gets accused of trying to be both extremes, and is rejected. Hard for me to figure out what the writer intended.