This has been collecting dust bunnies on my hard drive since July 30th of last year. So enjoy this random and rather ridiculous one-shot featuring the two most overly confident characters of the Palmwoods attempting to date. Set after and inspired by Big Time Single.
James didn't really know what to say, which was a completely new feeling for him. And he didn't like it at all. He swiped his mirror out of his back pocket, giving himself a quick look-over. He looked fantastic, of course. Or at least, he thought he did. He wasn't really sure what she'd think. He wasn't sure what she thought of him in general at the moment. And James Diamond took the image he held in other people's minds very seriously. But even with that considered, he shouldn't have been as worried as he was about her opinion of him.
But he couldn't help himself. After dumping her, he'd realized that hey, she actually was pretty hot. Plus, she shared his interest in maintaining flawless appearances, aaand she knew that she was hot and she was definitely not ashamed of that. James certainly understood the feeling himself, so he admired her proud recognition of such a fact. He cleared his throat, readying himself for one of the greatest challenges he might ever face.
He glimpsed out the lobby door, cringing to see her in between her two friends, all three of them sipping low fat, gluten free smoothies. He shook his head, trying not to let the numbers worry him. He inhaled deeply and put on his best strut as he approached the pool table. Besides him of course, nobody had ever dated a Jennifer twice. Dating one three times was practically impossible. And this time, Katie didn't have some four hundred dollar leather jacket and James wasn't wearing a tux and holding a crisp bouquet of flowers, which lowered his chances even further. But still, he was the James Diamond. The James Diamond never took "no" for an answer. He'd learned that one from his mama back in his preschool days.
He stopped in front of the table, none of the Jennifers even looking up from their celebrity gossip magazines. He cleared his throat awkwardly, trying not to let his nerves get the best of him. The three girls looked up at him, raising their sunglasses perfectly in sync. It was kinda creepy. "Hello ladies," he began smoothly, laying on some of the classic Diamond charm.
"No," they all immediately answered, perfectly in sync again.
James frowned, "But I didn't even ask my question yet!"
"Look James," curly Jennifer said, laying her magazine down, "you ruined Jennifer's no break up rep."
"And that is totally unacceptable," brunette Jennifer said, her nose held high.
"So we won't be doing any more 'favors' for you any time soon," blonde Jennifer finished, "No matter what they are."
James' frown deepened, completely not expecting this disadvantageous turn of events. "Look, can I just speak to blonde Jennifer for a second? Alone?" he asked.
"Not happening," curly Jennifer said, picking up her magazine.
"Ever," brunette Jennifer added for good measure, also reopening her magazine.
James panicked inwardly, unsure of what to do. He didn't want to be reduced to the pitiful, desperate mess he'd become the second time he'd asked Jennifer out. And Kendall wasn't conveniently nearby with that wheelbarrow anymore. Growing more frantic, he blurted out the first idea that poofed into his mind. "If you don't let me talk to her, I'll tell everyone you three have head lice!"
All three girls immediately shrieked at the idea. "No one would believe you!" brunette Jennifer argued, "We're too gorgeous for…," she gulped, finishing the sentence with a shudder, "l-lice!"
"They will!" James shot back, "I'll say that that's why you wear sunhats all the time! You don't want people to see them crawling around in your ha—"
The Jennifers screamed again. Curly Jennifer clapped her hands over her ears and pinched her eyes shut, trying to block out the horrific idea. "Oh, make it stop! Make him stop!" she cried desperately.
"Jennifer, just go talk to him!" brunette Jennifer agreed, on the verge of tears just thinking about the rumors soon to be circulating about her beautiful little head.
Blonde Jennifer sniffled and bravely stood from her seat. "I'll do it for us," she said, boldly following James, "For our reps."
The other two Jennifers nodded their understanding, watching their blonde friend disappear into one of the cabanas with James, their admiration for her growing. Blonde Jennifer crossed her arms as James smiled at her. "Let's make this fast, ex-boyfriend."
James coughed into his fist, hoping maybe he could just exhale all the anxiety settling over his body so he could return to his normal, cool and collected self. Because he really hated this new person he became around blonde Jennifer. "Yeah, about that," he said, "I was thinking. And maybe, you know, we don't have to be, you know, exes. You know?"
Blonde Jennifer raised both eyebrows, very high up, at that. James stuttered, "I-I mean, I'm really hot and-and you're really hot too, so…why not, right?"
Blonde Jennifer raised a hand, stopping him. "No way," she stated, "I may have let you ruin my rep once before, but a Jennifer is never dumped twice. Especially by the same person."
James looked down at the ground sadly, "But I was thinking that maybe we didn't have to dump each other this time."
Blonde Jennifer raised an eyebrow again, this time with confusion, "You mean you want to date me—like for real date me?"
James nodded, looking up at her hopefully. "Sorry," Jennifer shook her head, "I only for real date celebrities."
"What? I'm a celebrity!" James sputtered in protest, "We had a hit album in Kerplankistan!"
Jennifer frowned, turning on her heel to leave, "Talk to me when you get in the top ten, but not before."
James panicked again. He was losing! His chance was slipping away! Another thing about Diamonds that his mama had taught him—they always date who they want to. When they want to. Acting on impulse again (since it worked last time, after all), he grabbed her wrist quickly, spinning her around and kissing her. Jennifer squeaked in objection, raising her free hand and smacking James across the face. "Stop that!" she snapped as he flinched, rubbing his cheek.
She turned to storm away, in a most stylish manner of course, when James caught her wrist again. "No!" he replied firmly, "I won't stop until you say you'll go out with me!"
Jennifer glared at him, "You are so immature!"
"Well, you're so stubborn!" James shot back.
"No, you're stubborn! And stupid!" Jennifer shot back.
"You're stupid!" James responded brilliantly.
"Just let me go!" Jennifer stamped her foot impatiently.
"Just go out with me!" James demanded.
"No!"
"Why not?"
"Because you're not famous! I can barely brag about my rep anymore, thanks to you! And dating you a third time will just make me look desperate and totes unfabulous!"
"But-but I'm hot!" James protested.
Jennifer cocked her head to one side thoughtfully, "True, but you're still not famous."
"And I'm a good kisser too," James added proudly, "Don't forget that."
"You were decent, but you still haven't topped the charts," she pointed out.
"But I have," James stepped closer, their noses bumping, "In Kerplankistan."
Hoping his timing was more accurate than the last and also hoping to further convince her, James joined their lips again. This time, Jennifer didn't smack him. She stood there, her eyes blinking shut until James pulled back, waiting expectantly for her reaction.
After a pause, she asked cautiously, "Were you in the top five there?"
James grinned confidently, "We were number one there! We were a huge hit—veeery famous."
Jennifer frowned thoughtfully, "And you're sure people know about this? It's a really big deal?"
"Ginormous deal," James assured her.
She sighed, "Fine. But! You came bawling to me about making the worst decision of your life, and I only took you back after you promised to buy me a Portia and a snow leopard."
"Got it," James instantly replied, excitement mounting within him at his progress, "Wait…could I maybe be crying, like—in a hot, manly way instead of 'bawling?'"
Jennifer rolled her eyes, "Whatever. And if you ever dump me again, the other Jennifers and I will find you. And when we're done with you, you'll feel worse than Ashley Johnson did when I kissed her boyfriend, got the latest gossip on her from her best friend, and beat her as homecoming queen. In the same night."
James nodded his understanding giddily, more than ecstatic that he'd just accomplished the impossible. Not that he hadn't known from the start that he could or anything. Jennifer turned to leave, but James stopped her a third time, their fingers tangling together. She looked at him with exasperation, "What now?"
"…can we kiss some more?" James asked hopefully.
Jennifer rolled her eyes with annoyance, "One more time. But make it quick. I have a mani pedi in fifteen minutes and you're smearing my lip gloss."
James smiled victoriously, leaning down and kissing her again, more gently than before. Kissing Jennifer was awesome. And they could totally make this relationship work. They'd had practice at being a couple, after all. Twice. Jennifer tried to pull away from the kiss, but James threw his arms around her waist, refusing to let her move. Another thing about Diamonds—they kissed for as long as they wanted to, no exceptions. And when James began effortlessly moving their lips together, Jennifer didn't seem to mind the Diamond way all that much. Yep, this was awesome.