I’m thinking this is set in season 2ish while jenna was still in the picture and elena was still dating stefan

askbigbrolucifer: heart-on-her-sleeve: “Oh, here,” Elena smiled, poking the back button on her phone. The previous song began to fill the car’s speakers once again. “It seems like you have a good support system, Anthony. I’m really happy for you.” She couldn’t help but be happy that he was raised in a loving family, even if it wasn’tContinue reading