He knew long before He ever came to Earth how the Jews were going to treat the Samaritains. He knew about the life that this woman had lived. He knew what time of day she would be at the well. He knew that the Jews would rather take an extra day and bypass Samaria all together than to walk through it. He knew all this yet, He set this time to meet with her to show her that God is love and cares about her no matter who she is and what she has done.
His disciples had left Him all alone at the well around noon, as they went to the town to seek food, when she approaches the well. Going there at noon hoping to avoid everyone, imagine the shock as she saw the figure of a man resting there. She sought to be there at that time so that she didn't have to hear the other women gossip and whisper about her. Now there was a man at the well. As she drew closer she saw that He was a Jew. What to do? Does she go on to the well and go about getting water as if He wasn't there or does she go back and wait a couple hours hoping He will be gone by then? She decided to go on to the well instead of lugging the heavy jar back and forth empty. Besides most Jews didn't want anything to do with the people of Samaria. Did He get lost or was He looking to set a trap for her.
It appears that she had no family and could have been used by the men of the city. She had five husbands, at that time if a woman didn't make her husband happy for basically any reason, like she burnt the dinner, he could divorce her. At this point of time she was not married but sleeping with a married man. No wonder why she could have mistrust in her heart towards men. The Jews treated the Samaritains as an none human and had nothing to do with them. If they did interact there was some sort of trick behind it. This could have also led to her fear and anger towards the Jews. Let alone the hurt from all the gossip of the women and having to go at the hottest time of day to avoid everyone had to sting at her heart.
Like many of us, the hurts of the past leads to fear and mistrusting people. I had a hard time being able to look anyone in the eyes and speak loudly because I was afraid that they would yell at me for who knows what; even a waitress because in my mind it would play out that she might come back at me with, "Are you sure you want that? This would be better. I'll get you this." Over and over my mistrust and fear would play out different scenarios in my mind about my interaction with people and they were always wrong yet I let it control me for years. So like the woman at the well I just wanted to get what I needed to do most of the time done and not having to deal much with people.