Early millennial 2000s geek humor and peak 4chan lingo. What a golden time, never again will we experience such peak language comedy. Everyone had thick skin back then. Can't bust out that kind of verbiage now-a-days. Absolutely forbidden.
For anyone wandering why the anime is like this its because the anime failed in Japan so when it was being dubbed they didnt give a shit how it was done. So the american voice actors started seeing how much shit they could get away with and no one ever told them to stop.
When Tiffany mentions her dream wedding, Chucky has a look of remorse like he feels bad for fucking up her life and dreams then he apologizes and I freaking love that