Best Contestshipping Moments (Pokemon)
Contestshipping is the paring of Drew & May in Pokemon. While I’ve seen a lot of Pokemon ships that focused on Ash ships, I thought of doing something different. It seems contestshipping is usually only focused on as a secondary ship to dump May away from Ash, but there is a lot to like about contestshipping than that (even though advanceshipping is pretty cute too).
A lot have speculated that contestshipping is one sided on Drew’s side, but this hint makes it seem like that is not the case. May blushes at drew her with it being shown for like 5 while seconds (emphasis) & she doesn’t looked pissed, she wasn’t sick, there was no need for her to be embarrassed, she wasn’t crying... so this could seem like she likes drew too.

It shows that May is on Drew’s mind a lot, even solidad thinks so as she tells May that drew has feelings for her. - Mariosprincessesfan

Wow really? The picture was so sweet!
While may usually isn’t an action girl around ash, she jumped into a river to save drew & pleaded for him to say something. She risks her safety for drew, & as shown in the other items drew goes out of his way to help her as well. - Mariosprincessesfan

May is drew’s rival & they where in the same contest, So May getting tricked into doing something stupid would benefit him as well. But drew didn’t like that Harley was tricking her, so he told her what Harley was actually doing to her, & saved her from continuing to make that mistake & fail. - Mariosprincessesfan
It shows May respects Drew’s talent like he respects her talents. - Mariosprincessesfan

She remembers all the times they spent together & shows that she constantly thinks about him like he thinks about her. - Mariosprincessesfan

It was even told by Brock & it says they have completely different battle styles. - Mariosprincessesfan

First time he admits to watching out for May. - Mariosprincessesfan

Roselia is like his first Pokemon & his main Pokemon as we always see it walk beside him so it’s pretty big to see it tease drew about May. - Mariosprincessesfan

Red roses are romantic & he’s given it to her many times thoughout the episode. He says it’s for beautifly, but May raised beautifly & came up with the combinations for it. So saying it’s for beautifly was most likely used to hid his true feelings for her or to tease her. - Mariosprincessesfan
May could have continued travelling with Ash but she chose to follow Drew to Johto. Along with Solidad and Harley. And she has not returned to anime since the Wallace cup.
No, she went to Johto alone. Ash headed back home meanwhile.

They stare at each other with great attraction.