See here's my thing with the whole Jess situation.. Rory told him to wait twice and he kept going which is not okay. In my opinion he deserved to be punched because being in a bad mood doesnt excuse how you treat your girlfriend, especially if it is going to be crossing her boundaries to not have sex in that moment. Now should it have been Dean punching him? Absolutely not, espcially because he doesnt know why Rory was upset, but I don't feel sorry for Jess at all.