Hey. Did you read how to transfer the save files over on the itch season 2 page?
You need a save file that is AFTER the Daniella and MC night club scene. Prefereably one where MC drops her off at home. Any playthrough save after that point will work in S2. Once you have copied over the save folder with your saves as mentioned above, then use the "Continue to load" button at main menu of Season 2 game. This will ask you if you want to see the girls you were close with in Season 1 and then start Season 2.