itch.io

1.  You roll the dice and compare to your attribute every time you roll a scenario (so once per round/day).
   
2. When each Love Interest's heart metre reaches 1, 3, 6 and 10 hearts for the first time in your playthrough (this is not counting the option time travelling rule), you will get a date event the next day before the scenario occurs. For each date event, roll the appropriate date event tables (should be on page 6). Then after that, you get a reward listed under the Hearts section (should be on the right most column on page 1). 
   1. For example, for 1 Heart reward, you may roll an additional die and choose the best outcome, whenever you want to. But you can only do this once. The 3 Hearts and 6 Hearts rewards are the same. You can only use that reward once.
   2. For 10 Hearts reward, there are 6 options. You can roll or choose one that you prefer. Unlike 1, 3, 6 Hearts reward, the reward is permanent. For example, if you pick the reward "choose an additional number for critical success", the number that you pick will be your additional critical success number no matter how many rounds have passed. If you choose "roll an additional die. Choose the best outcome", you roll +1d6 from now on until the end of the game.

I hope it clarifies the rule somewhat. Please let me know if you have more questions!