Most of these

Also that he got shot and that his father died!

Also his mom betraying him and getting shot.

Anything having to do with his family.

this really fucked him up

Also his father died..

And his father died
and he got a shot in Prague

he was so lost then. and also the with Elizabeth.

There's nothing worse than this. :'(

I feel like this hurt him more than anything.

Damn my poor Chuckles has been through a lot of terrible things! My my poor baby :'(

It seems like C has the worst ones

that was one of the best storyline.
also his mom, and getting shot

dead parent trumps all.

This includes his belief that he killed his mother and his baaaad relationship with his father.

For me, it's not Bart dying that was so horrible, it was Bart dying while having a terrible relationship with Chuck.

Getting shot on some dirty street in Prague for protecting an engagement ring you bought for the girl who rejected you because you nailed the blonde jailbait you once attempted to rape who the girl you go rejected by hates and who had previously been trying to nail your best friend, who is with your step sister who you once also tried to rape and who is besties with the girl you proposed too...... MUST SUCK!

Hahahah ah I had too. Gossip Girl is awesomely incestous :)

On a more serious note: Poor Chuckles :(

which was the start of all the horrible things later.
of course his father's death was horrible too, but somehow I find this mother thing more awful.

i mean..WTF?

his mother betrayed him and gave his hotel to Jack that was very horrible to

and he got shot.