See, to me it was more of a response to Richard's wide-eyed attitude. You notice that none of the other parents were interacting with one another, they were just mostly fixated on the competition. You could tell by the way Richard was acting that he was new to that whole world. So 'this must be your first time' seemed like a cautionary thing. Like 'you have no idea what you're getting yourself into'.

I mean, the dude had headphones on. Not like he was into it.