I read somewhere that their japanese names are literal opposites of each other - Haruka means spring and Shuu means autumn, or something to that effect? If this is right, then Drew was quite literally designed to be her opposite from the startOriginally Posted by Encyclopika
We discussed when Drew's feelings for May started, but what about May's feelings? We are pretty sure she reciprocates, and we know it's later, but is it as late as we think?
This is actually quite a hard question. I've said before that I think May was written to be kind of a female version of Ash, and she shares his naivety and innocence, so I think she didn't start to suspect Drew's feeling towards her until Brianna pretty much pointed it out. The question is, had she started developing feelings towards him before this, or did she only start to look at him that way after she knew he liked her already?
I think she had begun to like him, but hadn't quite realised it yet. She starts to show interest and affection for him fairly early on, such as watching him practice with masquerain behind the pokemon centre, or the way she greets him happily and seems concerned at the beginning of Disaster of Disguise - she obviously never disliked him, and is actually the first to approach him on some occasions. The wynaut ep was probably when those feelings started to grow. She got to spend time one on one with Drew, they saved each others lives - the kind of stuff that makes good relationships I think this is the point where they start to respect each other, and I think its here that they start to consider each other as friends (May denies it in the GF, but it seems to me that shes being defensive because Harley had pointed out the romantic connotations of the rose). After he helps her out with Harley she definitely sees more of a friend in him, and she gets especially upset when he yells at her.
So by the time she meets Brianna, I think the foundations of her feelings towards him were there, but she needed someone to question it, to make her see them. After this, May starts to act a bit more coy around Drew, more flirty than friendly, and she becomes a lot more confident with him, teasing him back and so on.