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A/N: Sorry for being so inactive, I’ve had a lot of family issues lately and have had to tend to that. My sister is very sick right now. This is a Dazai x reader fic where Dazai falls first and harder (yes we’re being delulu). Y/N will use fem pronouns. No NSFW

Nostalgia was a familiar feeling to Dazai whenever he visited the Lupin Bar. He saved the visit for special days and times he was feeling especially alone. He was used to being alone, so all though the death of Odasaku hurt him, it was nothing different to his life of despair. However, he did have Y/N.

He remembered when he first met you during his dark days. Oda had recently deceased when he went for his last drink at the Lupin Bar as a Port Mafia executive. Thats when he ran into a beautiful girl around his age. He remembered thinking that there was no way for you two to meet again, for you were so innocent, bright, and hard-headed. Then when he joined the Armed Detective Agency, he caught your sparkling eyes that were so full of light. A part of him hoped that was fate.

Now here he was once again, drinking his feelings down with bitter whisky. He left a note on your desk earlier that day asking you to meet him here. He wanted to see that beautiful face of yours. You were always so eager to oblige to his silly requests and always checked on him throughout the day. He feared the feeling you invoked inside of him.

As he began to get lost in his thoughts, he heard the small door chime and light footsteps. He felt a smile plaster his face as he turned to look at you. You were still in your work clothes and looked a bit rough. However he found that your tired and effortless look embellished your beauty.

“Well, well. How are you bella’? Decided to hit the bar, didn’t you?”

Dazai’s smooth voice echoed in the small bar. He spoke with his usual dramatic tone and gestured for Y/N to sit next to him.

Y/N shook her head and smiled slightly as she took a seat by the man and ordered some whiskey. Dazai watched her every move, analyzing every possible detail he could. The dim lighting and soft jazz enhanced the adrenaline of being alone with you.

“You act like you didn’t specifically ask to meet me here. Or did you really forget that easily?”

Y/N teased the man beside her. She knew he was merely messing with her by acting oblivious to why she was here. She had known him for so long and thats she barely fell for his teasing anymore. Dazai chuckled at her question but didn’t respond. Y/N looked around the bar, her distant memory of the place being replenished. She had a feeling he hadn’t been in a while either, which piqued her curiosity.

“Why are we here?”

Y/N asked him, wondering if he had something planned or if he just felt like visiting. She knew his nature was unpredictable. Though a part of her found excitement in that.

Dazai chuckled at her question, leaving her momentarily more confused. He took another sip of his drink before answering.

“Why else would we be here? The drinks, of course.”

He answered in his own casual tone while leaning towards the table. It was obvious he was itching around the truth, not being used to opening up to others. His gaze turned somewhat cold when he finally regarded you, knowing you would only continue to ask if he lied.

“You could say I’m doing a bit of ‘reflection’ too…”

He said as he tapped the crystal ball in his drink. Y/N simply chuckled when he eventually added to his response. He always tried lying to her like he did with others but she was very persistent. Something about her made him want to spill his heart out. Or maybe it was just the alcohol working in his system. Though Y/N understood what he meant when he said he was reflecting. She had known him since those days after all.

“I think reflection is the main reason you came here.”

She commented, calling out his lies and attempts to downplay the truth. However, she knew not to press it too much. The past was a sensitive subject after all.

“It’s funny. This is the same place I met the most impactful people of my life.”

Dazai said as he looked forward with an expression of reminiscent. Y/N assumed he was only talking about Oda and Ango. It barely grazed her mind that she could be one of those people. Before the conversation could get any deeper, Dazai spoke again, interrupting the intensity of his past.

“Well then, how was your day? Boring, I presume?”

He asked, wanting to know more about you, even if it was small details. He always downplayed his questions, making it seem like he didn’t care as much as he did. Y/N smiled and thought about her day.

“It was fine.”

Normally she would’ve said more, and would engage more enthusiastically. Though today, her mind was reeling, specifically about Dazai. He was being so confusing lately and sending many mixed signals. She knew she had to ask him about it, even if she knew he would try and dodge it.

“I actually have been wanting to ask how you have been. You seem off recently.”

Y/N asked, concern hinted in her voice. Dazai’s eyes briefly widened, as if he was found her comment amusing. He couldn’t fathom the fact that someone like her would ever spend her time worrying over him.

“Of course, I’m perfectly fine.”

That familiar, charming smile embraced Y/N, though today, it seemed more forced than usual. In truth, Dazai was also reeling over her. Y/N didn’t like it, the silence and the unspoken words.

“Ugh… Osamu.”

Her voice came out soft and genuine. It wasn’t often she said his first name, she had only said it a few rare times.

“Why can’t you understand that I care for you?”

She would be met with silence after that, as Dazai had no idea how to respond. How could someone like her care for damaged goods like him? Though that same confusion had lately conquered his mind, forcing him to furthermore explore his feelings. He knew he felt something similar for her, but he dared not give it a name; labels were dangerous.

After what felt like a lifetime, Y/N finally sat up with a sigh. If he wasn’t going to address anything, then she wasn’t going to entertain him longer. She bid a quiet farewell and “see you tomorrow”, before starting to head towards the door. As her hand caught hold of the handle, Dazai called her name. Her eyes met his warm, dark eyes.

Dazai thought of Oda. His first friend and the reason why he left the Mafia, now dead. It was silly but Dazai always blamed himself. Everything was his fault. He wanted to tell you how he felt, he truly wanted to. But seeing your bright eyes that were so full of light, ones that he would only ruin, deterred him once more.

I like this one called “bed side table” on ao3, you should check it out and then tell us how it was!

I don’t remember what it was called but I read one where Beast Chuuya met ADA Dazai after Beast Dazai had just died and they spend a day with each other. It was pretty angsty but I really liked it, along with some other fanfics that I don’t remember the name of (I’m bad at not bookmarking things I like 😔). I always like things with depth and emotion though.

During the time Dazai was still in the PM, he would pester you both about it CONSTANTLY. You always seemed to laugh it off though, not seeming as bothered as Chuuya was. Chuuya would definitely try to make moves during moments of confidence, but that ego would crush whenever you flirted back in that playful, non serious manner. (He just doesn’t know that you’re being serious).

Whenever you talk about your crushes or who you think is attractive he’d judge your tastes so hard. He would literally be baffled whenever you show him your “ugly” and “weak” crush and would lecture you on how you deserve someone better. Anytime one of you go to a party or get-together, the other is always coming with. The only reason why it takes him so long to finally admit his feelings is because of how close you are to each other and your inability to take a hint. (Hate to break it to you Chuuya babes, but bragging and trying to act nonchalant are not the best flirting techniques).

Though as you grow older and he starts to mature more in his feelings, you can definitely see a difference in how he approaches things. He would invite you to have wine and would finally confess in a way he deemed fit.

“Y’know, I’ve lost about everyone close to me in childhood except you.” He wasn’t looking at you. His gaze was stuck to the dark red liquid in his fancy glass.

“Aw Chuuya… I hope you know I would do anything for you.” You smile sweetly, thinking he was just being sentimental again.

“I know. I would do the same. All because I love you.” He finally looked at you when he said that, a romantic but slightly egotistic smile on his face. He wanted you to know his feelings, but he already knew how you would respond. Of course he was confident!

You blushed and stammered but before you could even respond, the two of you instinctively moved in for a kiss.

Chuuya would be a very attentive and loving partner, always trying his hardest to please you. Despite his work in the PM, he would do everything in his power to be there for you, even if you’re also in the PM. Your relationship as an official couple wouldn’t be much different than yours as friends, except now you guys are more comfortable touching and being romantic. You still have your gossip sessions and play fights.

Chuuya would just be glad to have someone to love who loves him almost as much. His loyalty would be strong for you and he’s always by your side to assist you. He’s literally the best lover you could ask for and would spoil you soo much (you know he can with that PM executive money 🤑).

Tw: Slightly suggestive comment, but I’m not sure 😭

Dazai being pathetic in the way that he constantly clings to you and pouting about the littlest of things. However, you shouldn’t mistake this behavior as love-pfft! As if! The thought of a man as cruel and despicable as him indulging into the pleasures of loving someone, was more than humorous.

Though, sometimes he wondered if holding someone as beautiful and ethereal as you, could somehow mend his scarce heart. He found this thought silly, but interesting enough to entertain. Him-a former mafia executive and a current scum-possibly learning how to be as pure and benevolent as you, would truly be a phenomenon. Or perhaps, instead of him mending to be as considerate as you, maybe his sinful presence would corrupt you into becoming more like him.

Either choice wasn’t very likely, but that didn’t stop Dazai from dazing off about this. It wouldn’t be until you tap his shoulder and give him that oh-so adorable frustrated look.

“Dazai! You’ve been dazing off for 30 minutes now! Kunikida is going to yell at you if you don’t finish some paperwork.”

You would say with that concerned tone in your voice. He was a bit selfish in the way he loved seeing his loved ones worry about his own being. Something about it was soothing to his soul. Dazai of course would respond with a cheeky answer.

“Oh but belladonna! I’ve been spending my time quite productively thinking about all the ways we could spend our time once we’re alone! You see, I had the perfect plan to-“

You cut him off by interrupting him with more scolding. Your relationship had gotten to the point where you could more easily tell what he would say next, much to his dismay.

Dazai didn’t listen to a word you said this time. Instead he sat there with a soft gaze, pondering on his earlier thoughts. You really were starting to become everything to him. Or maybe you were all along, and he’s just now noticing this. You eventually realized he wasn’t listening to you and decided to walk away with a sassy eye roll, causing Dazai to chuckle to himself. Perhaps love wasn’t so far from him than he thought, and instead it came in many different forms. It was obvious he couldn’t love normally like most humans, but it might not be an experience reserved for normal, healthy people.

Of course though, this certainly didn’t matter either way. He was a vile man with no hope and he warned you at the beginning of your relationship. Nothing could change his mind for he was nothing in this vast earth, unlike you. For now, he’ll have to settle with his own torturous mind before even considering “love”.

The end?