If I were Drew, I'd temporarily join the group conspire with Brock.
As for how to get Ash and May together, hehehe, well I'd need to time it perfectly during the time Sceptile's heart was broken (Sorry Sceptile)
First, get May to acknowledge her feelings for Ash while Brock does the same with Ash. Oh and we all promise to get them together or die trying when Brock finds out Ash returns the feeling.
Then, make Ash jealous through a series of "coincidences" that look like they could be romantic but really they're friendship (I'd make sure that it was friendship, the point is to get May and Ash together).
So then one day we get Ash to stumble across something friendly like a hug but make it look like its romantic. He'll run away and be jealous.
That evening when Ash and Brock are training with Sceptile and Sceptile is totally failing at training because he's still heartbroken, Ash, naturally, goes and gives him a pep talk and tell him he emphathizes. Meanwhile, I'll go make sure May is nearby.
Brock pretends to be clueless and asks him why Ash and May aren't already together. So Ash gives this big emotional speech about how he's madly in love with May but he's heartbroken because he thinks me and May are together.
So then Brock'll say he understands and emphathizes as well and brings up some girl like Suzy (Back in Kanto/Johto I believe, she got together with another breeder and Brock backed off out of respect). But then Brock would tell Ash that he can't beat himself up about it and tells him that out of his own feelings, he let Suzy get together with that other guy whom he knew she'd be happy with.
So of course Brock pops the "Can you accept it and stay friends" question. So Ash thinks about it for a second and finally decides that he'll leave May alone, for the sake of her happiness.
Then when May moves in (probably after some gentle pushing) Brock and I leave the scene and watch them confess to each other ^_^. Oh and give each other brofists, never forget those.