A/N: This drabble was done on a dare, from BubChan on the Shipper's Truth or Dare thread, on Serebii.

The prompt was ImageShipping, involving coffee somehow.

I also took inspiration from the Tumblr AU ("We're bad at dating" edition, by user notallbees) prompt of "You're my waiter, and I'm on a crappy date with a [jerk]".

So, enjoy my first foray into writing fanfic for this fandom! XD

Warnings: pairings include Misty/May (ImageShipping), and some failed Annie/May. (Annie is from the movie "Pokemon Heroes".) As such, this contains femslash, though there's nothing explicit. Annie is the designated "jerk" from that prompt, and once again, please remember that this is an AU, and just for fun, so it's not my best work in the world. I've censored swearing out of the prompt and fic, for once, so need to worry about that.

(Though, uh, if any kids from Serebii decide to check out any of my other fics, please mind the warnings, as not all of my work is cussing-free. Just an fyi.)

Dedication: To BubChan! If you do decide to read this, hope it's to your satisfaction! :)

Disclaimer: I don't own anything of Pokemon. The title is taken from a lyric of the song "Take a Chance on Me", from Little Women the Musical.

We Could Fly on Golden Wings

If nothing else, then this date would teach her to not be such a pushover and a stammering, blushing, awkward mess when confronted with a pretty face and a hot body asking her out.

May had met Annie at the gym, which she rarely managed to drag herself to. May, whose self-confidence always took a bit of a blow after a session of working out and then remembering that she was terrible at exercising and precisely why she avoided it, hadn't been able to bring herself to say no to a date in the face of Annie's aggressive flirtations, and had been cowed by super-model looks that not even sweat had put a dent in.

May had tried to justify it to herself—how often did someone so hot ask someone like her out to coffee, especially when ramen noodles were more toned than her muscles? Answer: exactly zero people had ever asked her out.

And look at how this was turning out.

Annie was probably the most vapid, self-centered, and egotistical person May had ever encountered. All Annie ever seemed to think about was herself; for the past hour and a half, May had been treated to the world's longest monologue about everything to do with Annie. She didn't even seem to require any participation from May, as she'd stopped making polite noises an hour ago, but that didn't seem to have deterred Annie, as she was still talking. Annie hadn't asked even the most cursory of questions about May herself.

May was bored out of her skull, and had now descended to the level of desperation and loser-dom that she was making pointed eye-contact with their waitress in a silent plea for rescue.

The redhead's nametag declared her as MISTY, and May could have kissed her when she finally got the message and took pity on May and intervened.

Although, May wasn't certain if even Annie had deserved having their coffee refills being spilled on her. Still, she couldn't deny that Misty's method was effective, as Annie stormed out of the café.

"Don't worry," Misty reassured her, in response to May's wince. "The coffee was cold; I'd been letting it sit for a while."

That startled May into giggling. "Why?"

Misty shrugged. "She's been in here before, and was an absolute nightmare. I've been wanting to do that all week. So, thanks for the opportunity."

"I should be thanking you," May said earnestly. "And won't you get in trouble with your boss?"

Misty shrugged again, unconcerned. "Don't worry about that," Misty told her with a smile; it lit up her blue eyes, and May felt a swarm of butterflies swoop in her stomach.

"Still…what if I bought you a coffee on your break; to make up for all of this?" May offered, feeling unexpectedly bold, and internally cursing when her cheeks heated up with a blush anyway.

Misty's gentle smile widened into a grin, and some laughter escaped her. "Make it a latte, and you've got a deal."