She knew her daughter had been having a tough time despite her not showing it, Stars Hallow never was her scene.

She was mostly alone, watching movies, reading and listening to music.

So when Luke’s nephew, Jess was sent to town by his mother she could see her daughter finding a company, though they had a pretty hateful, sarcastic way of communicating. Lorelai knew she wanted to bring this up, so she suspiciously stood by your doorway, observing you.