Ollie lifted his hat up to his forehead with one finger and turned slightly to look at her when she accepted his offer (or he accepted hers, he wasn't entirely sure which had happened there), and listened, with his mouth shut for once. He looked at her when her smile changed and she put her headset on...
... and for the first time since SHIELD had picked him up, he broke into a grin and watched her for a minute longer with a contemplative expression. He was sure she couldn't hear him after she put those headphones on, but all the same he added, "I'd put my money on you." before settling back in and once again dropping his hat over his face-- though this time, it actually was to take a well deserved nap.