Cerulean Cape there's your obstacle.

Penn felt some trepidation as she approached, but he kept up his facade of joy (was it a facade, Penn? Really?) He didn't like others knowing when he was upset, unless it was anger. Anger was cool. Weepy sad sads were lame. And Penn Blackthorn was anything but lame.

He snickered at her retort, but didn't offer one of his own. He ought to have, he realized when the next question came. It might've distracted her from asking that shit question about things he didn't like to talk about. But he was being cool Penn, so he gave a nonchalant shrug and did his best to sidestep the whole Where's Fenn? conversation. "Something like that, I guess," he commented, "I've been traveling solo the past few weeks. I stopped by the Copse to shake off some baggage, but you guys were already gone. What's the story behind that? You still hangin' around with Wraen?" 

He left no time to question further about said "baggage" and merely crossed his toes that she would be distracted with telling her own story rather than have him expand upon his.