“flip-flopping helmet head in a pants suit” – this refers to Hilary Clinton, who is running for president. Flip-flopping means changing your opinion often (going back and forth between the two sides – in other words, flipping back and forth between the two sides). Helmet head is what you get when you wear a helmet and then take it off – your hair doesn’t look so good afterwards (similar to “hat head”). A pants suit is just a normal suit with pants and a jacket that a woman wears – Hilary Clinton is famous for wearing them all the time.

Paul Ryan is the Speaker of the US House of Representatives, and also ran for Vice President with Mitt Romney in 2012. He might run for president in 2020, which would make Schmidt quite happy. Presidential elections in the US occur every 4 years.

to register new voters – before you are allowed to vote, you have to register. It’s a simple process, and just consists of filling out a basic form. However, not everyone in the US does this (because they don’t know how, have forgotten about it, or are lazy), so some people go around the city or hold events to help encourage people to do this.

“A woman’s place is in the house. The White House.” – they are making a joke about a traditional sexist saying “a woman’s place is in the home/kitchen.” This saying means that women shouldn’t work.