Someone once told Sakura that Sasuke liked long hair.
When he was still a student, Itachi used to watch him, coming up to the academy to pick up his little sister Hana.
Cousin Shisui wouldn't look back, walking away with his sister's long black ponytail hanging down his back as she sat on his shoulders. Eventually Itachi got used to walking home alone.
He continued to watch, though, and when Shisui still came the day after Hana-chan's death, he didn't know what to say when Shisui stood in front of him and asked if he'd like to walk home together.
Itachi said yes, and later he wished he hadn't.