In Elogium we saw how utterly unprepared he was for an adult relationship. Full of jealousy that his girlfriend might want someone else's companionship and then freaking out when she makes it very clear she wants him
. Fucked it right up.
And because of that embarrassment it's all uphill from there. It was the last hurrah of whatever rogueish itinerant personality they envisaged for the original character. Every thing else he does in on the upside of the learning curve.