"There's a critical point, when you've stayed single too long, that your brain switches from "No, don't say that" to "Eh, fuck it. Say it, see what happens."

“Realize that sleeping on a futon when you're 30 is not the worst thing. You know what's worse? Sleeping in a king bed next to a wife you're not really in love with but for some reason married, and you got a couple kids, and you got a job you hate. You'll be laying there fantasizing about sleeping on a futon. There's no risk when you go after a dream. There's a tremendous amount to risk to playing it safe.”

“Rub one out like a man, it's the champagne of victory.”

“I get sick of people making excuses for her. She blew it. Look, you lost to a guy who said three things a week that would torpedo anybody else's campaign. How do you do that? That's like you're playing a football game and the other team throws twenty interceptions, and you still figure out how to blow it. At what point do you take responsibility? ... You blew it. You. Blew it. You put the wrong team around you, you didn't generate enough excitement to beat this guy who tripping over one coffee table after another...”

“Women are just constantly patting themselves on the back about how difficult their lives are and no one corrects 'em cause they wanna fuck 'em.”

“That's what killed me, when Bruce became Caitlin, that was like, a national news story, like at a ridiculous level. There's like, baby seals washing up on the beach cause there's no fish left, and they're talking to this... lady, you know, like, "So Bruce, can your Olympic back handle a D cup or you gonna go with something a little more perky?"... I miss that guy. I miss him already. He should've told us. He should've given us a chance to say goodbye. I watched him on the Olympics. I watched him on Chips. I watched him on that horrible show my wife watched where he just walks around in the background... And then you couldn't react, you couldn't on any level, you couldn't "What the f?" on any level. You couldn't say that or you were automatically homophobic. Like, dude, I didn't hear your inner thoughts. I didn't know what you were doing... You shave your beard off, people are like "Oh my God, that's your chin? Wow!" This guy walked out a dude, came back a woman, and you're just supposed to be like, "Oh yeah, so anyways, Caitlin, ...”

“Dude, any job that you can do in your pajamas is not a difficult job, alright? You're 35 years old playing hide and go seek... you're living the dream! No time card, no taxes... you're off the fucking grid!”