When has Grayson ever felt the lowest/saddest in his life? (Any instances)
There are only a few low points in his life. He’s generally pretty content but there are four moments I would consider the lowest/saddest in his life! (He would only say three, he refuses to acknowledge this last one.)
First, when Grayson was 13 his father passed away very suddenly and it destroyed him.
Second, in university when his roommate and first real friend vanished. This info isn’t set in stone in his canon yet so I won’t go too in depth, but this was the second big loss that really affected him. (You may recognize his university roommate as Alec Underwood who belongs to @macthedke)
Third, when his fiancée, Simone died. They were on a roadtrip and were planning to elope at the end. To make things more tragic Grayson found out Simone was pregnant only after she died.
Lastly, (and I am not going to provide context just because I think it’s funnier that way) is when he kissed his mother and attempted to seduce her only to be rejected. This caused him to flee the country and change his name to the Grayson Winters we know him as!