It's pretty easy. All you do is, once you're on the date, (I think all of them but the "playful" one you take to the beach) You give them 3 gifts, at first you dont know what they like, so it's a bit of trial and error. But after the 3 gifts, the progress bar at the top will be close to full, if you're at the beach, take them to the beach towel on the right and click the action, you'll give them a massage by just holding on the part of the body they say, either hard or soft. The one you take to the arcade, you play the whack-a-mole game with her, of course after three gifts, the bar should fill up after that and you can end the date. Then go to call them again, but instead of actually calling them, there's a "Story" button to the top right of the UI that shows up. It'll show 0/1 next to the word Story, if you did the successful date, you click that and watch a cute cutscene, or you can skip it if you just wanna get to the sex. Sorry if i explained that more complicated than i needed to. 👍