From what I can tell, the second pub date with Kleio and Amy will give you a series of choices, and you'll need to make the correct ones to get at least 4 out of 5 possible points with each girl. The best choices are, in order "Handle the first round" (requires enough money and charm), "Well, that's a shame!" (requires guitar skill), "Play fair" (requires shooting skill), "Play against Kleio and Amy" (requires enough knowledge), and finally "Why choose?" (requires foodie skill).
What makes this somewhat harsh is that all other choices result in +1 point to one girl and -1 to the other, so in practice, you'll need both the foodie and the shooting skill or you'll at best get 3 points with at least 1 girl and fail the best outcome requirement (and also the guitar skill, but it can be learned and I'm not sure you can even get to this event if you don't already have it).
I'm not sure if this is intentional or not, but it'd make more sense if the choices didn't subtract points so that it'd be possible to fail one choice and still get the best outcome. Especially since the only way to acquire either of those skills as far as I know is to pick them during the intro. Since you'll also need both, not only do you have to pick one during the intro, you then must do a NG+ and pick the other one too. I assume this is not intentional and something that should be fixed, or otherwise reconsidered. By comparison, the date with Anna/Amy only requires sufficient fitness and charm to get access to the correct choices, and the Sasha/Amy date doesn't have any requirements.