Somewhere along the line, Ash began to realize James wasn't as bad as his Team Rocket uniform made him out to be. When he wasn't stalking him and his friends or trying to kidnap pokemon from their trainers and homes, he almost seemed...nice.
He was more goofy than he was evil, Ash figured, and he was always kind to his pokemon. He'd given up a life of wealth and privilege for Jessie and Meowth. Most bad guys weren't such kind pokemon trainers or loyal friends.
Or so good-looking, Ash realized one day much to his chagrin. Even if James wasn't the enemy he was still another guy, and way older than him to boot. Dammit, maybe he is evil after all! Damn you, James, making me wonder if I'm not straight!
Then again, he'd never felt like this about other guys. Or girls. James was some weird exception.
Over the years, Ash continued to see James in this different light. Eight years later, when he'd accomplished his goal of Pokemon Mastery and Jessie and James left Team Rocket to run a flower shop, the former enemies' paths crossed once again.
"I almost didn't recognize you without Pikachu on your shoulder," James chuckled.
"Yeah, he's helping my mom and Mimey around the house," Ash said. "I almost didn't recognize you without the big red iR/i on your chest."
"It's been a while, hasn't it?" James rubbed the back of his head. "Um...you're looking well!"
"Yeah, you too. Nice place," Ash said, shoving his hands into his pockets. "So..."
"So..."
Silence followed, then James cleared his throat.
"I have a break coming up soon," he said. "Would you like to do something?"
"S-sure, I'd love to!" Ash smiled. A few minutes later, they were sitting in a cafe sipping coffee and reminiscing about old times. And every now and then, Ash could swear he saw James giving him meaningful looks...and he found himself returning those looks in kind.
Maybe now that they were older and more mature, this old flame could grow brighter. But only time would tell.