No matter how much I interact with Adam, I apparently nevr make a good enough attempt at endearing myself to him, either I'm missing something or this game is just broken
You can tell if your relationship is positive enough by his welcome and goodbye dialogues - they'll change to be friendlier if you have enough points for him to step in.
Otherwise, if you're still having trouble, try saying a few positive things (always agree with him, show interest, and don't tell him you want to leave), and then choose to wait with him instead of getting caught elsewhere. Staying with someone is worth multiple points and will get you there unless you've been choosing negatively-received options
Hope this helps!