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If you ever asked Dazai about how he feels, he'll put up his mask and say he's doing well. However, he can't feel anything at all in reality. It's always been that way.
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That all changed when he met ex Sheep king, Chuuya Nakahara at fifteen. He fell in love with him and his ability at first sight. Upon the Tainted Sorrow and Chuuya were the most beautiful things he will ever see in his life. After a bunch of bickerings (and Kouyou's assistance) later, the two finally started going out with each other at seventeen. It was not easy for the two to actually communicate with each other, but they eventually made it work.
Then, Dazai met Oda Sakunosuke at Bar Lupin at eighteen. The older man could understand his emotions well better than Chuuya did. However, he could never place what Dazai was thinking. The two men both equally understood Dazai, but only a piece of him. When Oda died in his arms, all he could feel was numbness, despite the tears wetting his face. The promise he made to him was just a sign of respect for the other man, not that he was willing to change on his own accord. After he fled the Port Mafia, leaving his first and only lover behind in the dust and hiding underground for four years, he still felt that feeling of numbness. He did feel some form of guilt for leaving Chuuya behind, but he still felt numb as he tried crying himself to sleep in his dirty shipping container.
After years of hiding, he was recruited to join the Armed Detective Agency, where he met his new partner Kunikida Doppo. Despite their contrasting personalities, they made to be great partners for each other. However, there were times that Dazai called Kunikida 'Chuuya' during one of their missions or used the secret language that him and Chuuya made when they were Soukoku.
When he and Chuuya reunited in the Port Mafia Dungeons after four years, the other man did not hesitate to brutally attack him. Dazai kept on his mask and taunted his former lover. He knew that the ginger was still not over him, and he was definitely not over him either. After being freed from him, they had numerous missions together due to their organizations teaming up. Dazai did not mind at all, but he knew that Chuuya was secretly hurting inside when they were called to missions.
Once Dazai was arrested by the Hunting Dogs and transported to Meursault, all he could think of was Chuuya and how much he missed him. He often sent messages to Ango to check on him. He wished there was a way that the Special Division member could send back responses to him.
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As Sigma stood next to him, Dazai talked to Fyodor through the control room's microphone. His rival and former lover were both drowning to death, all he felt was nothing. There were feelings of gulit and sadness forming in his throat, and it was becoming uncomfortable to bare as he talked. He stopped talking to Fyodor, and started talking to Chuuya.
"Chuuya, this is my farewell to you too. From the seven years since we met, all we've done is quarrel with each other but now I think of it. There were moments when our hearts reached out to each other like-" He paused, thinking for a moment. "Sorry, there weren't any! Well then goodbye!" He said as tears started to drop from his eyes and gulit and sadness consumed his whole throat.
As the water consumed Fyodor and Chuuya, Dazai whispered so quietly that Sigma could not hear,
"I love you, my Chuuya. We'll meet agan in another life."