A/N: I wrote this one-shot a few months ago when the Team Rocket discord added a Wendy-centric channel. I wrote Wendy closer to how my best friend and I tend to her write her but I didn't post this immediatly because I was worried Jessie was too OOC. But I almost died at the beginning of this month and I need to post SOMETHING before pride is over so I thought why not? I'll post this. Enjoy!

"Jessie dear, if you want a chance with me YOU are paying for dinner. And I get to pick the location."

That was the stipulation Wendy had set up when Jessie had asked her out.

The pair's relationship had been… complicated to say the least. Wendy had been one of Jessie's many partners during her time as a field agent trainee. Wendy would tell anyone that would listen that her trainee partner was so horrid that she quit her field agent training and moved to HR. She would never proclaim this partner was Jessie due to plausible deniability, but everyone knew who she referred to. Jessie and her partners, James and Meowth, had a pretty mixed reception within Team Rocket. Everyone considered them fools and unfit for Team Rocket but after their (questionable) victory against Team Galactic in Sinnoh they were at least seen as a valuable asset with weird schemes. One thing did stay consistent for the trio all those years, and that thing was their debts that were always being racked up. What always confused Jessie about her debts was that damn fruit smoothie. It was always on their invoices, and it was a debt solely placed on Jessie's head. One day, when most rocket members were summoned to HQ for a mission, she decided she'd march down to HR herself and have a word with whoever was billing her.

Jessie did remember Wendy but had no idea she was still with Team Rocket. When Jessie entered her office she didn't remember the infamous fruit smoothie incident where Jessie put the burden of paying on Wendy. Even if she had remembered, she wouldn't have expected Wendy to still insist she should be paid back after all these years and still charge her for it. She even added a ridiculous interest to her smoothie fee.

"Seriously, what is the meaning of this!?" Jessie shouted as she slammed her hand on Wendy's desk.

"Well if you don't pay your debts on time interest adds up-"

Jessie cut Wendy off. "You don't charge interest on a fruit smoothie purchased who knows how long ago!"

"Then let me make something very clear right now Jessie," Wendy said with a silent fury as she stood up and leaned close to Jessie, glaring at her all the while. "I am not your friend."

This escalated into a fight in the office, there was kicking, dragging, and hair-pulling. Somehow one of Wendy's missed kicks left a dent in her metal desk, making the other concerned Team Rocket workers in the vicinity wonder what the hell Jessie was made out of to take Wendy's hits so well. When their fight was broken up they were dragged to Viper, who was usually in charge of these sorts of issues, and he heard them out.

"You both almost destroyed an office… OVER A STUPID FRUIT SMOOTHIE!?"

"Right! That's what I said!" Jessie said eagerly.

"Shut it, agent!" Viper ordered and Jessie sealed her lips.

"Wendy, take the interest off of this smoothie, it isn't worth enough to charge interest anyway. And you Jessie, buy the girl a damn smoothie so you're even. That's an order!"

After that both girls sulked downstairs, Jessie tried to lead Wendy to the gym to buy one, but Wendy stopped her.

"He never said you had to buy me a fruit smoothie here, we are going to a place that I really like," after she said that she dragged Jessie out the door and into town where there was a cafe that sold fruit smoothies, they looked good but Jessie cringed at the prices. They were almost as much as a gourmet malasada in Alola. But still Jessie had to bite her tongue, her job was on the line! As she bought the fruit smoothie for Wendy, she saw it tear threw out her already dwindling wallet size so she just had to sit with a glass of ice water as Wendy took her sweet time to enjoy her smoothie. The looks of enjoyment on Wendy's face were utilized like weapons aimed at Jessie's neck.

"You don't gotta moan like a dying Dewgong just from drinking a smoothie," Jessie said as she bitterly sipped her water.

"These are moans of pleasure Jessie, not that you would know anything about that with your personality-"

"I know pleasure just fine!" Jessie replied.

"Really? Can you show me?" Wendy said with a smirk as she rested her chin on her hands.

"Show you?" Jessie said as it took her brain a few seconds to process. Finally getting the memo she began to blush while seething with anger. "Wha-no-IN YOUR DREAMS!"

"I think maybe you want to pleasure me Jessie~"

"Stop that!"

"You started it," Wendy huffed as she crossed her legs and turned away from Jessie. Both of their faces were still red as they stayed in silence.

"I mean…" Jessie's anger settled down a bit as she looked over at Wendy. Her hair was still a bit messy from their fight, the afternoon sun cast her in a soft glow. Looking at her ex-partner she felt like she was a young trainee again and she became tongue-tied.

"We haven't seen each other in a while…Do you wanna catch up or something?" Jessie asked.

"Are you asking me out?" Wendy asked, a look of shock on her face. "Just so you know I don't do hookups-"

"I"m not trying to insinuate anything, you psycho! Let's just hang out like we used to!" Jessie said with an annoyed tone as Wendy just smirked at her. That's when the green-haired woman gave her the before-mentioned ultimatum.

Jessie stood in front of her mirror, she had put on a nice pink dress and was now checking to make sure her hair looked nice.

"Are ya sure this ain't a date Jess?" Meowth asked as he walked up to the fretting Jessie. James was right behind him.

"It's not," Jessie said with her brow furrowed.

"I mean you're wearing fancy threads," Meowth said.

"It's because Wendy picked out some fancy location. She's just trying to one-up me but I'll win this battle!" Jessie said as she pumped up her fist.

"Who goes to a fancy dinner with their rival? I agree with Meowth, this sounds a lot like a date," James chimed in.

"Well... It's not! I have higher standards than someone with a fucking smoothie fetish!" Jessie snapped at the two. "At least my company card feels lighter after all that stupid interest was taken off."

"Was the interest really that bad?" Meowth asked as Jessie twirled the card between her fingers.

"You don't even know the half of it," Jessie sighed.

"If you don't leave now you're gonna be late to your outing-"

"DATE!" Jessie cut James off.

"Oh? I thought you said it wasn't a date," James said with a shit-eating grin.

"No, I thought you were gonna say it was a date- ARGH! I DON'T NEED TO EXPLAIN MYSELF TO YOU TWO!" Jessie yelled as she stormed out and slammed the door behind her. James and Meowth were just left alone, a little beat from the yelling but still utterly amused by the situation.

Jessie met up with Wendy just in time to not be late. It really didn't help that this location was far from HQ.

"We can't eat locally. If someone from HR were to be seen having an indecent workplace relationship, my job would be at stake," That's what Wendy had told her.

But just like Jessie had told James and Meowth, this was NOT a date! Jessie had a plan, she was going to make Wendy's night miserable as revenge for making her pay for dinner at such an expensive place.

"Ah Jessie, I almost thought you were gonna stand me up," Wendy said when she saw Jessie. Wendy wore a sleeveless black dress that was sculpted perfectly to her curves. It looked good on her, not that Jessie would tell her that. She did, however, look at those tight-fitting clothes and the curves they enhanced a little too long as the two women were led to their seats and given their menus. This was one of those fancy restaurants that didn't display the prices of their meals on the menus which just frustrated Jessie even further.

"I think I'm gonna get the… Apricot Berry Gratin," Jessie said, it looked like a meal that would be at a reasonable price. "Do you want to split a bottle of wine?"

"Wine sounds good. I prefer red wine," Wendy said as she kept eyeing up the menu.

"I think I'll get the Slowpoke tail," Wendy decided.

"What!? Those practically cost an arm and a leg!" Jessie balked when she heard it.

"Well you agreed to the terms of this date-"

"Outing."

"Whatever you say," Wendy said with a chuckle. The waiter came and took their order. He soon brought out their wine and with the alcohol in their system, the two started to loosen up a little bit.

"Really? Did she say that? God, Matori really is a piece of work," Wendy said as she dangled her wine glass in her slender fingers. She kept its balance well but Jessie's eyes were drawn to her surprisingly toned arms that usually weren't seen in her covered-up uniform. Maybe she worked out a lot just to get more of those damned fruit smoothies, that was Jessie's hypothesis.

"One day I'm gonna outrank specs and when I get my hands on her, she'll be begging for mercy! Hahahaha!" Jessie said with an evil laugh, she even held her hand up to her face like she was a cheesy cartoon villainess.

"People at work are so annoying, you're lucky to be able to get away from it all, even though you still have to travel with somebody," Wendy said.

"Yeah, but I got lucky to have good partners. They may get on my nerves but they got my back," Jessie said gently. The soft look on her face when regarding her friends made Wendy's heart hurt a bit.

"Would things have been different for us if we had passed the Field Agent training together?" Wendy asked.

"We probably would have killed each other, if we weren't already arrested," Jessie said. "We just don't work together like that, but at least we can talk together like this."

"I guess you're right," Wendy agreed with a smile and another sip of her wine. "While it does get annoying, at least this type of work helps with my anger. When I'm mad I can direct it to somebody who fucked up or owes us money!"

"That feels like an abuse of power," Jessie joked.

"Of course it is, we work for an evil organization," Wendy responded. The two just laughed and continued their wine. Soon their food came out, along with another bottle of wine. The pair shared laughs and recollections throughout the evening, a stranger wouldn't have known that just this morning, those two were at each other's throats. But this dinner was a battle in of itself: A battle of wits and insults, but still, the malice was low. They enjoyed tormenting each other to no end.

"Would you ladies like anything else tonight?" The waiter asked.

"Nah I'm stuffed, do you want dessert?" Wendy asked Jessie.

"No thanks, my stomach is full and my wallet is empty," Jessie said with a defeated tone. "Just the check please."

The waiter brought out the check and it made Jessie physically flinch just to see the price, but just when she was about to lay her card down defeatedly, Wendy sighed and took the checkbook away from her.

"It can't be that bad. You are so overdramatic…" Wendy trailed off as her eyes scrolled down the bill. Soon she was so enraged that she almost resembled an inferno. Jessie was confused but Wendy stood up and grabbed another waiter by his necktie, her grip was so tight she was literally lifting him off the floor by his collar like a ragdoll.

"What the hell is this? 16000 Pokedollars for a Slowpoke tail! I could march down to Mahogany Town right now and they wouldn't charge me more than 10000 for the same thing! I don't even think they charge that much for Slowpoke tails in Kalos! This is a fucking scam!" Wendy started, drowning the waiter with her anger

"Could you please-"

"And another thing! You charged us the price for aged wine when we only drank young wine! You can't pull the wool over my eyes boy!" Wendy didn't give the poor waiter enough time to even speak. Jessie was just left stunned.

"Good evening, I am the manager here. Is there anything I can do to help you two ladies?" An older gentleman in a nice suit approached their table with a panicked look on her face.

"You guys are trying to bleed us dry with these prices!" Wendy said, shoving the bill at the manager.

"We can fix the wine price and give you a free dessert for the trouble. But the prices on the meals are fixed" The manager explained.

"Then you should have put the prices on your menu, you muk-guzzling cowards!" Wendy screeched.

"If you keep making a scene in this restaurant I will have to ask you two to leave. If you don't pay and leave I will have to get Officer Jenny involved," The manager said with a scowl.

"Fine we'll leave, as for the payment…" Wendy looked over to Jessie who hadn't even had a chance to join in on the screaming fest.

Wendy grabbed Jessie's hand and pulled her up and out of her seat. "Dine and dash!" Wendy called as she ran with Jessie out of the restaurant and into the cover of night. As soon as they were a safe distance away from the restaurant and the city Jessie and Wendy finally stopped running to take a breath.

"Wow… I can't believe you… A stickler for the rules ran out on the bill like that!" Jessie said. She was genuinely impressed. "And you charged me interest for my damn smoothie. You just skipped out on paying 25000 pokedollars!"

"It's a pride thing. Our grunts risk getting arrested to get some slowpoke tail and even we don't charge that much for them. A place like that has no honor," Wendy defended herself with a puff of her chest.

"A villain speaks of honor…" Jessie said with a cheeky side glance.

"I can do crimes and have standards," Wendy retorted. Jessie just laughed but nodded in agreement to what Wendy said.

"Well then the next time we go out let's find a place with more reasonable prices," Jessie said as she put her hand on Wendy's shoulder.

"You wanna eat with me again? Even after that?" Wendy asked.

"Yeah," Jessie said. Wendy stepped closer to Jessie, she could smell the wine on both of their breaths.

"And would you call it a date this time?" Wendy asked with a mischievous look in her eyes.

Instead of answering outright Jessie just smiled and leaned down to place a kiss on Wendy's lips. Their lips locked and eventually, they pulled away for breath, but soon they were back at it with their lips parted to make way for the tango their tongues performed in each other's mouths. Lost in the wine they had finally seemed to get a little closer on that bridge they burned years ago, and it felt great.

A/N: Leave a review if you enjoyed or if you hated it because I am an attention whore.