Yes, it's the second date, not the first.
For the double date on the second time, you need to not have went in the hotel the first time totally shit faced (you will go on Danny's road) and neither go all the way with the other when he get you home (you will go on Mike's road).
After that it's kind of automatic during the second date.
Yes, if you don't like choices, the game is definitely not for you, as choices are a heavy focus in my game.
Though none of them is really the best choice, it all depends on what you prefer, what you like and want to see, and this is why I went the choice way instead of going on a kinetic novel where you just sit for the ride, you're offered the possibility to make the game and its MC more your own.
But to each his own, everyone comes here with their tastes, kinks and preferences, I hope you find your perfect game out there, I know that I didn't myself and that's why I chose to try myself in making my own. ^^