The first time John Oliver asked someone out he was five years old living in Birmingham, UK, nervously inviting a fellow classmate named Sarah round for a playdate.
“What I liked about her is she had blue National Health issue glasses and very, very bright, shiny lacquer sandals,” Oliver explains being interviewed on The Late Show, before going off on an amusingly long-winded anecdote — egged on by Stephen Colbert — about the relationship that never was.
“I don’t know your current situation right now, Sarah, but I remember you,” Oliver says into the camera at the story’s conclusion. “When I say I remember you, I remember two accessories that you wore. If you still have those accessories that you had as a five-year-old — and even hearing this out loud I’m realising how alarming an approach this might come across to you — please get in touch at an email I will not give right now.”
