Rupert is either teasing him or being unreasonably kind. Jonas finds it impossible to imagine that this is anything other than a disappointment for him, smile or no.

Fumbling for excuses, he blurts, "It's been a long time." And then, when that doesn't feel like enough, he adds insistently, "I'm not a virgin." Which he realizes, once he's said it, probably only makes him look more like a virgin.