Sakura could be the one to find him crying. She has known Naruto for a long time and they are comrades. If Naruto is in a vulnerable state, she might stumble upon him.
One possible reason could be that Naruto is feeling lonely. Despite having friends, he still has moments when the weight of his past, like being an orphan and ostracized in the village as a child, hits him hard. Jiraiya might see Naruto crying because of these memories resurfacing.
One possible reason could be the loss of a dear friend. Naruto forms deep bonds with his comrades, and if something were to happen to them, like Sasuke leaving again, it would break his heart and make him cry.
Crying could be described according to different situations and characters. There were a few possible ways to describe it:
1. Crying sadly: The eyes are red and swollen, and the tears are constantly flowing. The lips are slightly opened, as if they are silently pouring out the pain in their hearts.
2. Crying in despair: Tears poured out like a waterfall. His eyes were hazy and he looked depressed as if he had lost all his strength.
3. Crying angrily: The eyes are red and swollen, and the tears are like boiling flames. The expression on the face also becomes angry and resentful.
4. Crying in surprise: Tears instantly gushed out of her eyes as if expressing her inner ecstasy and gratitude.
5. Crying in fear: Tears flow from the eyes. The trembling body and helpless heart make people feel fear and uneasiness in their hearts.
Different crying forms could show the character's inner emotions and personality characteristics, and at the same time, it could allow the reader to better understand the character's psychological state.
One possible fanfiction could be that Naruto is crying after a particularly tough mission where he lost a comrade. Jiraiya finds him and offers his fan, which has a special significance. He tells Naruto about his own losses and how he overcame them, inspiring Naruto to keep going.
Their relationship is like a mentor - mentee bond. Kakashi has trained Naruto, and when he sees Naruto achieve great things, it can be overwhelming. For example, when Naruto masters a new jutsu that Kakashi thought was difficult for him, Kakashi might cry out of joy for Naruto's accomplishment.
In the fanfiction, after Hinata sees Naruto crying, Naruto might initially try to hide his tears and put on a brave face. But Hinata's gentle persistence makes him break down further. This then leads to a chain of events where other characters start to notice the change in their relationship. Some might be supportive, while others could be jealous. The situation could also lead to Hinata and Naruto teaming up to face a common enemy or problem, with their newfound emotional bond strengthening their resolve.
Naruto's impulsive nature could be shown when he's crying. Maybe he cries because he rushed into a situation without thinking and it backfired. Shikamaru's cautious personality would then contrast as he scolds Naruto gently but also helps him fix the mess. This would show how their different personalities play off each other in the fanfic.
Perhaps Shikamaru has made a decision that deeply affects Naruto. For example, Shikamaru might choose to leave the village for a dangerous solo mission. Naruto, who values their friendship, cries because he's worried about Shikamaru's safety and the thought of losing his friend. In the fanfic, this could lead to Naruto trying to convince Shikamaru to change his mind.
Kakashi would probably first check if Naruto is hungry or needs a diaper change. If that's not the case, he might hold Naruto close and gently rock him while humming a soft tune.