Chapter Text
You had stalled in the break room until you were sure most of your fellow Grunts would be gone for the day before making your way to the locker room to change. As you opened the door two other girls were just coming out and you forced a smile and wave as they left before quickly dropping the cheery act as you headed to your locker. It was Valentine’s Day and you hadn’t intended to spend it alone, in fact, you still had reservations for later this evening for you and...No, you thought, you weren’t even going to think his name. He didn’t deserve it. Even though you hadn’t been together long, breaking up on today of all days was low. You yanked open your locker as you fought back tears, thankful that no one else was around to see you like this. Glancing at the small mirror in your locker you tried to push thoughts of him away but instead your reflection began to blur. You angrily swiped the tears out of your eyes with one hand while the other balled into a fist at your side, and you almost gave in to the strong urge to slam your fist into your locker. Instead an idea sparked in your mind and you grabbed a pair of leggings and tank top from your locker.
You slowly pushed open the door to the in-house gym, wincing as it creaked, and listened for signs of anyone else. Not hearing anything you stepped in and made sure the door shut gently behind you. It felt silly, sneaking into somewhere you had every right to be, but you really didn’t feel like running into anyone right now. You made your way over to the piece of equipment that had sparked this idea in the first place, the punching bag. Dropping your water bottle and towel next to it you popped in headphones, confident that if no one was here now there wouldn’t be anyone later given what day it was. It didn’t take long, especially as you pictured your newly ex-boyfriend’s face on the bag, to get in a zone and work up a sweat.
Cliff pushed back from his desk with a loud sigh, the last report of the day was finally finished and it was about time. He was the last one here, Sierra and Arlo had taken off early citing the holiday but Cliff didn’t have plans and figured he’d rather not let this work pile up for the next day. Standing up with a stretch he checked the time and was surprised to see it wasn’t as late as he had thought. Maybe there was some time to get a workout in before it got too late. He shut down his computer before changing in his office and heading down to the gym. As he opened the door he was surprised to hear someone else clearly going to town on the punching bag and was even more surprised to see who it was. You evidently hadn’t seen or heard him as you continued to take some kind of emotion out on the poor bag, something Cliff had to admit he wouldn’t have pictured you ever doing. You had joined Team Rocket a few months ago and had landed on his team. While the two of you had never had much interaction beyond a professional comment on training here and there you had definitely caught Cliff’s attention with your skill. And looks. Cliff thought as he found himself staring at you but quickly brushed the thoughts away. He was your boss after all, and he had heard you were dating someone anyway. Not wanting to startle you he cleared his throat to try and get your attention but was unsuccessful so he moved forward a few feet to try again. As he did you let out a shout and gave the bag a kick that sent it swinging right to where he had moved. He caught the bag with both hands as your hands flew to your face.
“Oh, I’m so sorry!” You exclaimed as you yanked your headphones out. “I didn’t know anyone was still here.” Shit. Shit. Shit. Why was he still here?!
“No worries. No harm done, although I don’t know if the same can be said for the bag.” He joked before catching the look on your face. Were those tears? He frowned. “Everything alright?”
“Yeah, mhmm, all good here.” You tried smiling. “Just...um…” No, no, no, no, no! You mentally yelled at yourself as the adrenaline began to wear off. You were pretty sure all the anger at your ex had been taken out and now all that was left was the hurt. But dammit, you weren’t going to cry in front of the boss! “Actually I was just leaving.” You bent down and grabbed your stuff intending to make a hasty retreat to the locker room but a warm hand on your shoulder stopped you.
“Are you sure you’re okay?” Cliff’s tone was gentle and sincere and you couldn’t stop the stream of hot tears that escaped your eyes this time. “Hey-” He began but you cut him off by standing up abruptly.
“I’m sorry, I shouldn’t be...I should go.”
“(Y/N).” Cliff looked at you with concern. He didn’t like that you were crying and had a sudden urge to know why and fix it. “Hey, you can talk to me, what’s wrong?”
“It’s...stupid.” You laughed at yourself as you brushed your cheeks with the back of your hand.
“If it has you this upset it isn’t stupid.”
You eyed Cliff for a long moment as you contemplated telling him. On one hand he was the boss and your ex was also on his team. On the other hand he did seem genuinely concerned right now. “It’s Steve. We...he just broke up with me.” You finally said, swallowing hard while not daring to look at your boss’s reaction.
“Oh, I’m sorry to hear that.” Cliff had heard that you two were dating and while it wasn’t good that you were upset a small part of him was glad you were now single.
“I told you it was stupid.” You let out a small laugh. Now that you had finally let yourself cry about it you felt better and a little silly. “It’s just...today of all days, ya know? I had reservations and everything...I’m sorry. I shouldn’t be complaining to you.”
“No, it’s fine, really!” Cliff smiled warmly at you and placed a hand on your shoulder, giving it a little squeeze. “My door is always open if you need to talk.”
“Thanks.” You smiled shyly back suddenly very much aware of the fact that you were alone in here with your boss. Your hot boss. You felt your face begin to turn red and knew you should probably leave before you made a fool of yourself again. “Well, I guess I should get going.”
“Are you sure you’re okay?” Now that you had said you were leaving Cliff realized he wanted to find a reason for you not to.
“Yeah, I’m good. Thanks.” You smiled at him again and Cliff’s heart beat a little bit faster in his chest.
“What about your reservations?” He asked as you began to turn away and was glad when you turned back.
“What?” You tilted your head to the side with a laugh.
“You said you had reservations for tonight. It would be a shame for it to go to waste. Why don’t I take you?”
You froze. Did your boss really just ask to take you to dinner?
Cliff took your reaction as a bad sign and tried backpedaling. “I mean, if you want. I would feel terrible letting you go home like this-.”
“Yes.” You interrupted him before you could change your mind. Like he said, it would be a shame if the reservation, not to mention the little red dress hanging in your closet, went to waste. And if you cleaned up quickly you should make it just in time. “That sounds nice.”
“Great. It’s my treat, you deserve it.” Cliff grinned. “For all your hard work, that is.” He added quickly hoping he didn’t sound too unprofessional, reminding himself again he was your boss.
You told him you needed to get cleaned up first and gave him your address to pick you up at in an hour. As soon as you were out of headquarters you began running, thanking Legendaries you didn’t live far. Before you knew it the hour was up and your doorbell was being rung. You took another quick look in the mirror, smoothing your hair one more time before grabbing your keys and opening the door.
To say Cliff was surprised would be an understatement. Aside from in the gym earlier he had only ever seen you in your Grunt uniform and seeing you in a dress, especially a dress like the one you had on, was a pleasant surprise. “Wow, (Y/N), you look stunning.”
“Thanks.” You blushed as you stepped outside. “You don’t look half bad yourself.” Cliff had ditched his Team Rocket uniform for black slacks and a blue button up shirt; that was tight in just the right places you found yourself thinking. He hurried to open the passenger door for you before getting in himself, following your directions to the restaurant.
The table you two were seated at was small and draped in a pink table cloth that was covered in red hearts with a bouquet of roses in the middle. You groaned internally having forgotten that you had chosen this place for the romantic atmosphere they were known for on this holiday.
“Ahh, sorry, I forgot about all this.” You smiled sheepishly.
“Don’t be.” Cliff seemed more amused than anything. “I understand, you weren’t supposed to be here with me.”
“Right…” Your heart sank a bit as he reminded you of what had happened this morning. Seeing your expression Cliff immediately regretted bringing it up.
“I’m sorry, (Y/N), I shouldn’t have mentioned it.”
“It’s okay.” You forced a smile and reached for your glass but were startled when Cliff placed his hand over yours.
“If it’s any consolation I think he’s an idiot. Any guy would be lucky to be here with you, (Y/N).” You met gazes across the table but you were fortunately saved from coming up with a response as the food arrived.
For the rest of the meal you avoided any mention of your ex and the obvious romantic setting this was supposed to be, soon forgetting about all that completely. Cliff was the perfect gentleman throughout and by the time the check came you were totally at ease and genuinely sad that you would be going home. It had actually been nice talking with him, he wasn’t all Team Rocket and protein powder like everyone assumed. And every time he smiled or laughed you felt a little flutter in your stomach.
“Thank you, I had a great time. I needed this.” Your sentiment was genuine but your smile was nervous as Cliff walked you to your door, he had insisted on it even after you pointed out it was only a few feet from the curb he was parked at.
“I’m glad. You deserved it.” Cliff surprised you, and himself, by reaching out to tuck a strand of your hair behind your ear. Realizing what he did he quickly pulled his hand back. “I’m sorry, I shouldn’t have-”
You cut off his apology by leaning up to kiss him. Maybe it was the day or the mood or the wine, not that you had had that much, or the way he had been smiling at you but in that moment you had just felt like it was the right thing to do. Your risk paid off when you felt his strong arm wrap around your waist and pull you closer to him. After a few moments you both pulled back.
“Does this mean I’m going to have to quit Team Rocket?” You joked, biting your lip as you looked up into his eyes.
“Quit? No. Change teams? Probably.” Cliff smiled again, melting your heart a little more, and brought a hand up to cup your face as his thumb traced a line across your cheek.
“I can live with that.” You laughed before he leaned in to kiss you again. This was definitely a better Valentine’s Day than you had expected.