You're My Hero (Sonic 3D Blast, Saturn Edition) - A retrospect type of song. If you want to think along the lines of Misty's life being pathetic and ruined before she met Ash, this works better. I believe the "set me free" lines are meant to be literal, as I think this song is supposed to be in the Flickies' point of view, but they can be taken from a metaphorical standpoint in my opinion, like the "break me out of this prison I call a life" kind of thing. The way this song is sung makes me believe it could take place post-GCYL, but it's not hard to think that Misty could be singing this to herself while traveling with Ash in the Original Series.
Worth a Chance (Sonic and the Secret Rings - I owe this song a lot, lol. This is the song that got me into this hobby, back into the Pokemon anime fandom, and back into Pokeshipping. I have no idea how a song from a separate franchise managed to do it, but whatever. This song screams "PS post-GCYL" to me. "Price of being aware, but too afraid it all might die," "It's for being unaware, I run away from things like that," "Let it be
rain that falls to make it up to you, all I never said," "Some things they never mend," "Only you can make, any sense to me," these lines were so in tune to what I thought PS was that I actually thought Sonic Team's workers were Pokeshippers XD. This song is about regret and sadness, and I like to play with the idea that Ash and Misty did have an idea of what was going on between them, but never outright admitted it, and have regretted it since. It's sad, but it's realistic to me.
Shotting Stars (Star Maze remix by WillRock07, Super Mario Land 2 -
Ghost of Maiden's Peak, the dance scene. This is a popular moment in the PS fandom, but when I try to think of a song to go along with Ash and Misty's "legendary" dance, nothing fits the bill quite as much as this song. It's cute, it sounds like it has a Japanese-setting to it when the wind and wood instruments come in, and it's calm enough to not be a crazy party song and take away from the moment. Just overall the best song I can think of for this scenario, with nothing else coming close to it.
Tropical Resort Act 1 (Sonic Colors) - .....nothing really shippy about it, but this is one of those themes I can imagine Ash and Misty running to when going to the next town, or when running while
in town. It's got that spunky feel and attitude to it that I think personifies PS, so I like to connect this song to them.
Aquarium Park Act 2 (Sonic Colors) - Same concept as above, but instead taking place at sea, near water, or underwater. Nothing more, nothing less.