Wesley remembered a time when Harry was still wary of him and it was actually their second meeting. He had caught sight of her walking from Walmart to head back home (he presumed). He knew her address and that her home was rather far away, so he didn't know why she was made to walk to and from her home and the store, and with groceries no less.
So he'd driven up to her, purposely forgetting that he'd just seen and talked with her in the store not too long ago, and rolled down his window.
"Do you need a ride?" he called out, stopping her.
She looked hesitant, but he didn't blame her. This was their second meeting and he was a stranger. A dangerous one as well, but she had no need to know that.
He reached over and opened the door on her side, putting a polite smile on his face. Wesley could be professional about this, even though he had a personal interest in her. He was good at being professional. It was what he did.
Wesley took care of things. And he'd take care of her.
"Yeah, okay," she muttered and slipped into the car.
He started to drive again and let her give him directions, despite the fact he already knew where she lived. Not that that was another thing she had needed to know. However, seeing him following directions and going where she wanted made her relax and not think the worse.
"Open that compartment, will you?" he pointed to the glove compartment. She did as he asked, snorting as she saw the new pack of Oreos he'd bought earlier with her.
Without further instructions or him needing to ask, Harry opened it and gave him one.
"You can have one if you want," at her hesitant look, he smirked. "Aside from the fact I just bought them and you were there when I did, it would be such a waste to poison you. I really wouldn't."
He had no problem setting up such a thing, but he wouldn't with her.
She took one finally, and he didn't hold back on his smug look.
"You're such a smug bastard," Harry grumbled.
He merely kept smirking, and thought it ironic they were sharing a pack of Oreos on their second meeting, when their first meeting ended with him asking if she liked them.
And that was how their daily meetings began.