Let's go through some basic knowledge before I talk about it further...

Characters: Ash Ketchum, May & Drew
Canonical: Semi-canon (Contestshipping)
Fanon (Advanceshipping and Respectshipping)
Relationship status: Mutual feelings on both (Contestshipping)
Friends (The rest)
Also known as: SatoHaruShuu

What do I think:

It looks cute but I think the relationship looks better without Ash

I shall rate this ship: 3/10