Sebastian (the dark-haired guy) spends most of the day in his room. You can’t enter a character’s room until you reach a certain level of friendship (usually by giving them “liked” or “loved” gifts). On rainy days, he spends some time by the river before returning home.

The player is waiting outside his house to interact with him.

Also, he’s one of the potential spouse characters in the game, so presumably the player plans to eventually marry him – or at least date him. (The “heart” threshold to enter his room and interact with him like a normal person is way lower than that.)

I hope I have sufficiently explained the joke to death. :D

Edit: Oh dang, the teardrop over the player’s head is a mineral (I forget the name), which is one of Sebastian’s “loved” items. When you’re holding something in-game it’s held over your head.