#i'll try to write endeavor more to get used to him quq

[chocochar]

Hallooo :) I must ask bcs' I need some fiery sugar....would you consider doing headcanons about, (yes you are reading it correctly 😂😂) ENDEAVOR. Like he on a first date with his s/o 🔥

HOOOOO boi I haven’t ever written for Endeavor, I’m gonna be 100% with you XD so I really hope this is okay, sorry it took so long, I rewrote it a few times and I’m sorry ahead of time if he comes off as OOC! TuT  (btw i loooove your Midnight Stalker fics, had to add that, okay onto the hc’s!)

🔥 Endeavor is, well, not the best person socially. In fact to most people he’s hard to get along with, so finding someone who cares for him despite this the older man wasn’t expecting.

🔥 (F/n) is quite a few years younger, but doesn’t seem to mind the gap in age, being in their 20′s. Having started working at his agency as a secretary (F/n) proved themselves quite efficiently, which that along with their looks and attitude Endeavor couldn’t help but start to watch them, glancing and feeling a softness in his chest that he’s never experienced. They didn’t show fear of him, even if he got mad they’d simply fix the mistake and even tell him to calm down.

🔥 Endeavor never planned to ask them out. The #1 hero dating a secretary? To him at first it was an embarrassing thought. Plus his track record with relationship is... not good and scarce. But as time went on and the hero slowly began to change inside inch by inch since becoming the big #1 that thought started becoming more appealing, even if Endeavor wouldn’t admit it.

🔥 It was Hawks who set up the date (kind of, he helped push it, and nearly lost his feathers for it). He saw the light blush dusting the fire users cheeks when (F/n) came up to them with documents, and he was quick to ask if they’re single and looking.

🔥 Endeavor tried to hide his interest when (F/n) said yes to both, but his flames burst high when Hawks grinned and asked,”Oh yeah? Well, are you interested in hot heads?” as he visibly gestured at Endeavor.

🔥 (F/n) understood, and glancing at Endeavor they were reluctant to say so at first, but once they saw the way the hero was eyeing them they blushed, turning back to Hawks and saying,”... Yeah, I actually am.”

🔥 Smiling they figured Endeavor may get mad, after all he couldn’t possibly be interested in them-

🔥 “Soooo how about dinner with Mr. Hot Head here?~” Hawks grinned, jutting a thumb at the red head standing beside him stiffly.

🔥 (F/n) was surprised, but replied,”I mean... I suppose yes-”

🔥 Hawks grinned wide and added,”Alright, I’ll set it up, don’t worry you two awkward love birds, it’ll be great.~” Endeavor hadn’t said a word the whole time, dumbfounded it seemed, not knowing what to say.

🔥 Hawks left. When (F/n) looked at Endeavor he was already leaving, but stopped with his back to them.

🔥 “Meet me at the address I’ll give you through text, at 8 PM Saturday. You have it off, correct?”

🔥 “Uh... Yes.”

🔥 “Good, don’t be late.” He left once he’d said what he needed to, (F/n) was shocked but smiling they go back to work.

🔥 Boooi (F/n) isn’t prepared for the expensive dinner waiting for them

🔥 They aren’t dressed up super fancy, they did their hair nicely and made themselves look presentable at least! After all, they’re going on a date with the #1 hero! And he definitely seems like an ‘appearance’s type of man from just working with him

🔥 The place is nice, and (F/n) settles in feeling a little out of place. Enji got them flowers and looks incredibly handsome in his tailored suit, the scar across his left eye not bothering them a bit even when he received it. His face looks red too, and they wonder if his heart is pounding a million beats a minute like theirs

🔥 “I’ve heard really good things about this place, have you been here before?” (F/n) breaks the silence that settles over them

🔥 “Yes, a few times,” he starts, going on to explain (in sparse detail) about the hero parties held here that he only came to due to his position as #2, now #1

🔥 Silence sits between them again after (F/n) replies, and they’re racking their brain for more to say

🔥 “You... Look nice tonight,” he says out of nowhere, catching the secretary off guard as they look taken aback, cheeks going red. “This isn’t too... Awkward, is it?”

🔥 Again fairly surprised by his sudden shyness (F/n) blinks before smiling. He is a socially awkward kind of guy, so shaking their head they decided to take the lead for the date, at least for now.

🔥 “Not at all, it’s nice,” they reply. This seems to put the #2 at ease as he nods and clears his throat, looking over the menu. (F/n) rests their chin on their palm and asks,”So, um... Enji, Tell me about yourself.”

🔥 It’s a simple request to help break the ice although (F/n) is already well aware their boss isn’t very forthcoming with information about himself. But this doesn’t change anything, after all they did come to dinner with him with this fact in mind. Enji cocks a brow, meeting their (eye color) orbs with his cerulean.

🔥 “Such as?”

🔥 “Y’know, favorite TV show, what you do in your spare time, do you like cats, etcetera, just some stuff so I know my date better, right now we’re more than just boss and secretary after all,” (F/n) winks, this gaining surprise from the normally uptight man. He brings the scowl (which he’s trying to reel in for tonight) back but he seems to be fine letting them know some answers. Not everything, he keeps the more personal aspects of himself under wraps for now, after all it’s only a first date, but the secretary across from him seems appeased and even smiles at the answers. “I see, I’m fairly surprised but you seem kinda normal.~” They tease, Endeavor averting his gaze.

🔥 “And you?” It’s his turn to learn about them more. Granted, he’s studied them, he knows some things but learning more never hurts.

🔥 “Well, I love to (hobby) and (hobby), my favorite show is (TV show), I’m probably more of a dog person, I am definitely a (night owl, morning person, etc), I like to make sure I’m always on time to things,” they start to tell him, answering any questions he has. Even if it’s a mundane conversation he is surprisingly taking every piece of information in and locking it up in his thoughts. That way, he knows for later. To be honest, he’s intrigued. (F/n) laughs lightly and finishes with,”Sorry, sorry, I was rambling, haha!”

🔥 “It’s fine.” Endeavor responds, telling the waiter what he’ll have. “I find you interesting, different compared to others I’ve met.”

🔥 “Is that a good thing?” (F/n) laughs, smiling warmly lifting their brows.

🔥 “Yes, very,” he replies, and even gives a small smile himself, although it’s easy to miss.

🔥 The two start to eat once their food is brought out and while they eat they talk, discussing not only more about themselves but Endeavor’s jobs, (F/n) plans for something at work, and more. Soon enough they’re done and after paying Enji takes (F/n) home, the drive even holding it’s own conversations. Enji surprisingly seems to have been brought out of his tough as steel shell although it’s only with (F/n), and (F/n) is content in his company, seeing the normally scary boss is surprisingly softer inside, under all the layers of anger and pride.

🔥 Reaching (F/n)’s address Enji parks and turns his gaze to the secretary, who’s getting ready to leave but stops to look at him.

🔥 “Thank you for dinner, Enji, it was delicious,” they sigh happily, smiling and he nods, (F/n) unbuckling and about to get out but stopping.

🔥 “Perhaps we can do it again, I enjoyed your company, (F/n),” the fiery red head admits, (F/n) nodding.

🔥 They surprise him with a kiss on the cheek before getting out of his car and peering back in at the blushing, taken aback older man.

🔥 “Of course, you have my number so call me and we’ll plan another date~”

🔥 The (brunette, blonde, etc) shuts the door and waves as they head inside their home, Enji not leaving right away as his heart pounds. Clearing his throat he watches them go in and shut their door before leaving, already planning to ask them out again (and keep this secret from Hawks lest Enji listen to the feathered annoyance tease him about)

AHHHHHHH I hope this was okay!! I kinda struggled with Enji so I hope he wasn’t too OOC QwQ thank you for the request!