It started, as many of life's most regrettable things do, during puberty.
The June sun, a sudden influx of hormones, and a bit of free time have never been particularly good influences on anyone's decision making, so perhaps it's not surprising that it began right at the end of the boys' second year of Hogwarts. There was just a week left before exams, and rather than spending it crammed around a library table, pouring over notes and books and worrying themselves over answers they either knew or didn't, the four boys decided to lark about on the Hogwarts lawn. This was nothing unusual as they had made a bit of a name for themselves already for exactly this type of behavior. It was also not unusual for the pretty girl with red hair and bright green eyes to glare up at them from where she sat with a circle of friends, books spread out amongst them.
So it's hard to say why the idea struck at that moment, but that's where it started.
"James," Sirius said, prompting James to look up from where he'd been turning a small frog he'd found different colors. "I'll give you ten sickles if you get Evans to go on a date with you."
James snorted, ruffling a hand through his hair and allowing the newly bright pink frog a chance to make its escape. "It'll take more than ten sickles for me to go on a date with Evans."
Peter cackled at this, and Sirius sat up a little straighter, leaning towards his best mate. "Name your price."
James turned his attention down the hill and the other boys followed his gaze to the group of girls circled further down on the lawn. Lily Evans was no longer glaring at them and was instead throwing balled up parchment at Marlene McKinnon who threw it back at the redhead as Mary Macdonald laughed. The boys watched as Florence Saise opened her mouth and said a few words which made Mary and Marlene keel over laughing and Lily turn very red indeed.
James rotated back to face Sirius.
"Ten sickles to ask, a galleon if she agrees."
Sirius barked out a laugh. "Ten sickles just for asking?" He narrowed his eyes at James, his grin shifting into something entirely too wolfish for Remus to be comfortable with where this conversation was going. "You don't think you can get her to say yes, do you?"
Remus' gaze shifted to James who had the same mulish look that always led to Gryffindor losing points.
"As if you could get her to say yes to you."
"Course I could," Sirius shrugged dismissively, "I could get any witch you named to go on a date with me."
This seemed to be exactly what James was hoping Sirius would say as he broke out into a smile. Remus' stomach dropped while Peter looked between James and Sirius, as if he were watching a particularly active Quidditch match. "Care to make a wager then?" James asked.
"Alright, name the terms?"
"I can get Lily Evans to go on a date with me before you can get…James looked around the lawn, and his smile turned positively devilish. "Florence Saise to go on a date with you."
"Saise?" Sirius repeated, a note of skepticism leaking into his voice.
"Something wrong with her?" James asked, looking very much like he had just won the bet before it'd even fully been placed.
"Not a whole lot right with her if I'm being honest, mate," Sirius remarked, his gaze drawn to the blonde down the lawn who was currently setting thistles on the lawn on fire before stamping it out with one of her shoes that she'd taken off.
"She's actually quite funny," Remus remarked, earning glances from his friends. "She was my partner in Transfiguration for the bit where McGonagall split us up."
"There you have it," James said, gesturing to Remus. "You go for Saise, I go for Evans, and the first one to snag a date wins."
Sirius appeared to think this over, narrowing his eyes in thought even as he remained focused on the group of girls. "Seems a bit easy, one date."
Both Remus and James frowned in confusion at Sirius. Nothing about getting Lily Evans or Florence Saise to date them seemed particularly easy. Lily had shown nothing but open disdain for James and Sirius' antics whereas Florence seemed entirely content on her own. Even amongst her group of friends, she was always quiet and reserved. Remus hadn't even gotten her to say as much as hello to him for the first two classes they sat next to each other.
"First one to get the girl to date him for a month wins ten galleons."
"Ten galleons?" Peter echoed at the same time James said,
"Deal."
