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His first unsuccessful flirting attempt was probably his own fault. Too ambiguous and terrible timing. He'd have to remember that for next time.
"You looked good out there," Bucky compliments as the two of you walk down the ramp of the Quinjet after a successful mission.
"Thank you!" you gleam. "All that training's finally paying off, isn't it?"
"That's not-"
"I'm glad I listened, you know? Not relying on powers and everything. That was some good advice, thanks!"
The second time was also, probably, mostly Bucky's fault. Or more accurately, it was both Sam and Bucky's fault.
Sam's for telling him the stupid, corny pickup line and Bucky for thinking that it would actually work. This, plus what was quickly becoming his signature: terrible timing. He'd duly note better timing for his next attempt at flirting.
"You alright?" he asks, extending a hand to help you off the ground after a rocky parachute landing.
You take his hand and stand with ease. "Yeah."
"I guess you've had worse falls than that," he awkwardly adds, helping you unclip the used chute. "Like when you fell from heaven."
"What?" you exhale, still dusting yourself off.
"I said when you-" but his words are almost entirely drowned out by the loud noises in the surrounding area. When he thought about this little plan, he didn't account for the fact that you two were going to be surrounded by open fire.
And that was probably his fault considering it was a field mission and whatnot.
The third and fourth time could in no way be blamed on Bucky.
Probably.
"Fancy seeing you here," he chuckles, walking into the training room to see you rolling up your mat.
"Hey!" you greet, an excitement in your voice makes Bucky the slightest bit more hopeful.
You pick up the rolled up mat from the floor and place it in the corner of the room, returning to where Bucky awkwardly stands in the room. "So, you, uh, you come here often?"
"To the training room?" you ask, a humorous grin pulling at the corner of your mouth.
"What I meant was- finishing up or just starting?"
"Oh," you nod. "Just finishing up."
"Well, if you ever need any help." You open your mouth to respond, but Bucky is quickly amending his statement before you can squeeze in a word, "Not that you need help, of course! But if you want- I could- we could do it together. Not it. But train-"
"Are you okay?" you ask, placing your hand on his arm and effectively cutting off his rambling tangent.
He nods, a pained, cringe-filled expression on his face as he gives you a wordless thumbs up.
The fourth time, he tried to channel the side of him that most people saw. Stoic, grumpy, but an air of confidence that was intimidating to most. A side of him you hadn't seen in almost a year. Maybe that would finally catch your attention.
"This is a little embarrassing," you quip, a faint blush on your cheeks as you try to free yourself from the massive tangle you found yourself in.
It was an accident, mostly caused because someone didn't put away some large safety nets instead leaving them in the middle of the hangar. You'd been fighting to free yourself for only a few short moments when Bucky walked in to see you trying to get the large nets off of you.
"I love it when you blush," he remarks, his voice low and more gruff than normal, as he gently grazes your cheek.
"I thought you didn't like it when people wear their heart on their sleeve?" you jokingly counter.
And for a moment, it trips Bucky up. Mostly because it almost sounds like you're finally flirting back. "Maybe you're the exception."
"Isn't that a song?"
"Huh?"
"Yeah, that's a song! I'm 99% sure it's a song."
"Er...I don't. Maybe?" he stammers, once again finding himself as the awkward man who didn't have any dating experience in the last 70 years.
"Anyway... I don't want to tell you what to do, but do you mind?" you politely ask, gesturing to your still entangled limbs.
"Oh, right!" he jolts.
The fifth time he couldn't have been more brazen- at least for a man from the 40's.
It was perfect, you were alone in the common room, no one else in sight, no one to interrupt, no guns blazing in the background.
He stood at the threshold in the room, plotting the entire conversation from beginning to end. From the jovial greeting, to the subtle transition to plans for dinner, and then he'd ask you out. It was the perfect way to end an eight month long game of cat and mouse.
"I'm starting to think you're obsessed with me," you tease, seeing him stand in the doorway a moment too long.
He tries to keep the cringe off of his otherwise neutral expression. He knows you're joking. He knows that. But also, he's kind of worried he looks like a stalker with all the times he kept 'accidentally' running into you.
You stand up off the bar stool, padding to the fridge to grab a drink.
"When you look like that, how couldn't I be?" he lilts, slowly but purposefully, dragging his eyes over you from head to toe.
"I had no idea you were into fashion. I learn something new about you every single day."
"No- what I mean- I"
You shake your head, already almost fully turned away from him. Over your shoulder, you chuckle, "You crack me up, James. You know that?"
And after almost an entire year of grueling obliviousness, the one time you finally noticed.
"Hey!" you greet, kneeling on the swivel chair in the conference room, papers splayed out all over the table. "I heard you were on this one with me."
"No one I'd rather be working with," he gruffly offers, winking at you.
"Aww, thanks. I like working with you too," you trill, turning back to your papers.
He watches you for a moment, the way you intently comb through the files, a complete 180 from your normal bubbly, energetic self, and without thinking, he says, "You're cute, you know that?"
You look away from your mission brief, eyebrows furrowed at Bucky. "Are you flirting with me?"
He looks up at you, almost completely bewildered. That, a little suggestive remark, that was what caught your attention? Not any of the less-than-subtle, obscenely flirtatious comments he tried squeezing into so many conversations. No, it was a flippant little comment that took him a year to get your attention. "Have been for the last year, but thanks for finally noticing."
"Wait- what?"
"Am I that bad at flirting?"
"You were flirting? Ohhhh, that makes more sense," you exhale. "I knew you weren't interested in fashion- duh."
"Well...that makes me feel a little better...and a little worse."
You turn back to the paper-filled table with a coy smile, "You know, you could've just asked me out? I would've said yes."
"Really?!" he asks, too eager to even remotely play it off. "I mean- yeah, would you- maybe wanna?"
"Hey, James," you interrupt, trying not to smile at his adorably flustered expression. "Do you wanna go out for dinner Friday night?"
"I'd really like that," he nods, a little shell-shocked by the turn of events.
With a brilliant smile, you nod definitively, "Great, it's a date."
"Great," he nods again, pulling his lips in to hide his quickly growing, goofy grin. He turns to walk out the door before he can ruin the moment. He turns around, still watching you though you've turned back to your papers. He keeps watching as he quickly strides out of the room, painfully clipping his arm in the doorway as he walks out.
You look back at him having heard the muted thud, but he's already out of your sight.
"Nailed it," he triumphantly mutters to himself, rubbing his semi-injured shoulder.