Could we have some hcs of playing hard to get with Dazai Osamu please? <3
Of course! I hope you like these!
Warnings: Suicide mention (because it's Dazai)
Dazai is a consummate flirt. If he thinks you’re attractive, there’s literally nothing to stop him grabbing your hand and stroking it, his eyes sparkling, while he asks if you’ll use your lovely fingers to choke him. And not in a kinky way.
Well, maybe also in the kinky way.
Anyway, he’s infamous for hitting on clients, witnesses, and serving staff wherever he goes, much to Kunikida’s dismay. Let’s say you’re someone he sees on the regular, so a server at a bar or a cafe he likes to frequent. Maybe even a bartender.
Dazai’s well aware that he’s a handsome bastard, and he’s used his looks to do plenty of things—skip out on his tab, get better service, get his phone back from an overbearing nurse, get information, you name it. It doesn’t always land but his success rate is a good 80%. Enough to give him a sense of confidence when he clocks you and immediately dials up the charm to 11.
What I’m trying to say is…Dazai’s a whore. <3
This normally works for him. He's used to being able to wrap people—especially people that don't know him—around his little finger. So when he spots a new bartender at his favourite haunt, he's quick to latch onto you. This might be anything from a little suave charm to full-on uwu eyes, but…it doesn't work?
Dazai is unperturbed. You're not the first tough nut he's had to crack. He just needs to find another avenue of attack.
Dazai Osamu is not paying his tab.
Even if you're not downright cold toward him, he just can't crack your mask of professionalism. He can't build any kind of rapport with you and to his dismay, you treat him the way you would any other patron. It hurts his pride a little bit. (Don't worry, it can withstand a few jabs.) He ends the night without making any kind of progress, but Dazai's not discouraged.
He returns several times that week, and the next. Always charming, always trying to chat you up. He doesn't repeat the silly requests to strangle him and tones down the dramatic reactions (a bit, but not completely).
It frustrates him when he can't make any headway with you, but the more you stonewall him, the more determined he is. He relishes a challenge. Please note that he's not the type to go the way of harassment—he's a good customer (aside from his penchant for not paying) and his flirting is pleasant, charming, usually trying to draw you into conversation.
The longer you remain a mystery, the more he actually, genuinely wants to know about you. Dazai starts to look forward to swinging by the bar and tossing a few cheesy pick-up lines your way, just to see if he can get a reaction out of you. He gets a taste of victory the first time he sees you trying to hide a smirk while you shake up a cocktail for another customer.
"Aah, you like that one, belladonna? I've got plenty more where that came from."
"Why doesn't that surprise me?" you retort.
Despite yourself, he starts to become one of your favourite patrons. Despite your resistance to his charms, he's very handsome, and you quite like having his lanky form lounging against your bar every evening. You kind of bask in his attention, even when you feel your will to resist him crumbling.
It takes a while, months even. At this point, Dazai flirts with you almost out of habit. The pair of you gossip about other regulars and your colleagues, and he occasionally shares tidbits about his daily life at the Armed Detective Agency. You're not sure whether you believe him half the time, it all sounds so farfetched.
You kind of meet in the middle. Dazai tones down his charm offensive, and you warm up to him, creating something more genuine between you. The conversation flows as easily as the drinks—he still hasn't paid his damn tab—and you sometimes perch on the barstool beside him to eat your lunch. He always steals some of your fried chicken snacks. Bastard.
"So," he asks one day, swirling his drink around the glass. "How about it?"
"I mean it this time!" Dazai protests, all innocence. "Just come grab some dessert with me. We don't even have to have a romantic float down the river together."