She is very insecure, afraid to make decisions and overall a coward, and this is not hate, this is a reality that many Josy fans admit (Hi Megenos). Why is it unclear, because I don’t see any strong life traumas or reasons that could lead to this. Family? Well, things aren't so bad for her. Dad adores her, yes, there are problems with Monica and her stepbrother, but it's not too serious like in other MGs families. Maybe a past failed relationship? Unanswered questions.
Josy urgently needs her own storyline and personal growth, otherwise there will be more people who adhere to “boring and basic”.
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I would also like to imagine how other girls who rejected him react to Oscar's crowing.
-Sage would have simply knocked him out with one punch (Although he is a loser and he would not have the courage to approach her, same with Quinn)
-Isabella would respond with a cool comeback, making Oscar feel insignificant.
-Jill, well, this is Jill from those episodes. She would have to be defended and Oscar thrown out. Ep.10 Jill could easily hit the balls.
-It’s the same with Maya, she needs a white knight.
-Zoey would have just laughed at him, the DIK version would have added a couple of punches, like with firefighter.
Depending on individual sensitivities, divorce can be traumatic for some people.
Josy being a rather emotional, compassionate and very intimidable character, the divorce of her parents may have created her uncertainties. Furthermore, we don't know much about her stepfather (Tommy's father), but he made her suffer a sort of psychological guilt when she chose to live with her father instead of staying with her mother. All this can easily, I think, explain Josy's emotional suffering.
