True, he was partially doing this to be annoying. It was a little funny to make her frustrated and flustered in what to say next. It also made her have to think more and more of how to stay clever. Perhaps it was being a Ravenclaw, or perhaps it was just his boredom and own frustration in life that lead him to challenge her mentally. That's all it was, right?
Looking at Jolie briefly, he raised an eyebrow as if to say 'we'll discuss this later'. To which he earned a confused shrug. It wasn't as if he could really expect his siblings to know all of their peers. Especially by name. But still, he was curious about this mystery girl. Perhaps Jolie could send word more about who she is while at school. Even if that was weird, the whole situation was weird. "It would be quite rude if I simply left you on your own. I will happily see to it that you arrive to your chaperone safely." Perhaps the person responsible for this stubborn girl will address her by name. He was simply curious... and stubborn. And he could see from the corner of his eye that Jolie was raising an eyebrow at him, and he knew that he would need to inform her of the other encounters with the young lady at another time.
Looking at Jolie briefly, he raised an eyebrow as if to say 'we'll discuss this later'. To which he earned a confused shrug. It wasn't as if he could really expect his siblings to know all of their peers. Especially by name. But still, he was curious about this mystery girl. Perhaps Jolie could send word more about who she is while at school. Even if that was weird, the whole situation was weird. "It would be quite rude if I simply left you on your own. I will happily see to it that you arrive to your chaperone safely." Perhaps the person responsible for this stubborn girl will address her by name. He was simply curious... and stubborn. And he could see from the corner of his eye that Jolie was raising an eyebrow at him, and he knew that he would need to inform her of the other encounters with the young lady at another time.

