I've been stepping back from main quests as I've gotten to the point where faction choice time seems near. I'm currently going through all the companions to get their affinity up and do their quests.
I'm currently on Piper, and she's at about affinity 624, so I assume I'll get her quest at about 750. I don't want to just go back and grind through radiant quests, and have done pretty much all small side tasks I can think of, like checking tower distress signals.
Unfortunately I failed the flirt option with here, because it came up when we were checking the relay tower signals at the glowing sea, and it was too risky to change into my charisma clothes. I'm not sure, but I don't think they give you more flirt options after you fail them.
BTW, I already know she likes it when you loot typewriters, but I'm running out of places to find them. maybe I missed the best spots though.