Scampering off to the first shiny thing she saw was a real concern, with Penny. It wasn't like she was super-concerned with acting like an adult in front of Dare, who was present for most of the best childlike times she had (see: amusement parks, Halloween parties/trick-or-treating, arcade days, etc), and she was pretty hyper about the entire fair event. So his restraining arm around her shoulder was definitely a good thing for him, and it was done in such a way that she didn't even feel like she'd just been leashed. Instead of snarling at him, Penny just tilted her head and smirked, then shrugged lightly against him. "Uh-huh," she said, a little skeptically, but she wasn't really worried about the frat-boys.
She was too excited to be worried for silly frat-boys.
Dare's voice in her mind, as familiar to her as his arm around her shoulder, and twice as comforting, turned that smirk into a mischievous smile. After years of listening to him whisper in her mind, she wasn't bothered by his presence there... and she trusted him not to go rummaging through her personal thoughts. At his nudge, she slipped out from under his arm and strolled toward the ring toss, where she delivered the requested squeal (over a stuffed unicorn, no less, one which the carnie moved over to try and convince her to play for immediately.)
Penny didn't have to look to know that Dare was sliding through the crowd, relieving at least one of them (and probably more than that) of wallets or money stuck in pockets. At the very least, spending time with her morally-gray companion had taught her better places to keep her cash. He appeared beside her within a few moments, and she beamed up at him before pointing out the unicorn she'd been squealing over. "Look, it's sparkly! Can you win it for me, Dare? Pretty please?"