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Chuck Bass was born the son of Bart Bass, self-made billionaire and CEO. As a child he was given everything money could buy (including stock certificates rather than toys for Christmas) and some stunningly inept parenting. He was told that his mother had died in childbirth (which was retconned into a lie in S3) but grew up without a mother either way - and a difficult relationship with his father who cares for him and cares deeply, but doesn't have a clue what he is doing and never asks for help. Prior to canon, he's slept with many women (he can charm his way into beds but often pays hookers instead) but the closest thing he's had to a relationship was when he was 11 with Georgina Sparks - probably the most evil and fucked up character on a show full of them.

S1 Canon notes: The pilot was before the writers had decided on the character of Chuck Bass. I therefore count the Chuck in the pilot as 'Charlie Trout' - Dan Humphrey's version of events. (For instance he didn't try to physically force himself on either Serena or Jenny - although he did get the latter drunk). Also in the events surrounding the swimming pool, it was Chuck that told Bart what had happened so Bart could bail his sister-to-be out rather than let her be expelled. (How Bart knew is never made clear in the series, and that's the only version of events that works that I can see).

Normally end of Season 2 Chuck Bass - I refuse to acknowledge many of the events of Season 3.

Disclaimer: I am not and don't own Chuck Bass. Mun and muse over 18.