In a lot of ways, Ruby is like Sam in that regard. He has been pissed off at Dean before for moving his books out of order or using his laptop to create more work. Also he will ask her later if she'd like him to tag along in acquiring the rest of what she needs so next time --if there is a next time-- his gesture can be more meaningful. Helping her to perk up right now is his goal. When she's near, it's hard not to be able to breath in the scent of her body wash and not grow a little intoxicated with the scent. It's a plus that she's wearing her heels because he likes the ease of eye contact. He pretends to consider her proposal, only for a second. "I don't know how I can say no to you, but you will have to point me in the right direction." After all, the wards become invisible after going up.

There's enough promptness in his behavior to suggest he's caught on to her deeper meaning. If she will give him a second, he will place the stuff he has and find the magical featured brushes she used last time untouched in the box on the dresser.