Spiritfarer: Farewell Edition

This is missable but can be done in one playthrough by force quitting the game with Sealed Lips.

Near the end of Astrids storyline, you’ll get a quest called “I have my doubts”. The quest will conclude with you heading to Oxbury.

When you head back to the ship afterwards, you’ll get a prompt to talk to Astrid in the morning. You’ll have the option Yes or No. Choose either option to get the respective achievement. Then force quit the game and press continue on main menu. Sleep until morning again and choose the other option to get both achievements without having to do 2 playthrough

Through your journey, Astrid and Giovanni will join your ship. Their storylines are directly connected up to the ends of their journeys. Toward the end of their story you will unlock two quests, "I Have My Doubts" and "Indiscreet Meeting". Complete "Indiscreet Meeting", by taking Giovanni to Oxbury and then follow and spy on him while there. When you return to the ship, save and quit the game before talking to Astrid. Reload and talk to Astrid. You can choose to tell her the truth or lie about Giovanni. After choosing one of the options, you will earn either Loose Lips or Sealed Lips based on your choice. Then reload your save and talk to Astrid again, choosing the other option to unlock whichever achievement / trophy you didn't unlock the first time.