Shuichi Akai and Akemi Miyano
Shuichi Akai and Akemi Miyano were lovers while he was infiltrating the Black Organization. Shuichi's original mission was to date Akemi Miyano in order to meet Shiho Miyano. Shuichi used Shiho's influence to gain rank in the Organization, intending to become trusted enough to meet with high level agents so the FBI could capture one for questioning. As James Black later recalls, although Shuichi's relationship with Akemi was merely a stepping stone, Shuichi actually fell in love with Akemi, and considered her his real girlfriend. Because of this he broke up with the woman (and felow agent) he dated until then, Jodie Starling; he cared deeply for Jodie, but since he had fallen for Akemi he didn't want to keep two parallel relationships.
Sometime later, Akemi develops the suspicion that Shuichi really wasn't who he claimed to be. Later, due to a massive error by Andre Camel, Shuichi is discovered by the rest of the Organization to be an FBI agent, leading to his expulsion. Shuichi confirms that he is an FBI agent to her. To Shuichi's surprise, Akemi doesn't seemed surprised by this, so Shuichi asks her why she never said anything about her suspicions that she was being used by him before, and Akemi hints it is because she loves him. Initially, the Organization couldn't do anything about Akemi because they needed the loyalty of her sister, but two years later they decided that the risk of her contact with Shuichi was too much. They decided to create a situation where they could eliminate her by having her do a bank heist she was supposed to fail. Sometime near the day of the heist, Akemi sent Shuichi a long text message, asking him if he wants to be her real boyfriend when she is finally free from the Organization. There is an unrevealed P.S. After the heist, Akemi is killed by Gin, and it is unknown how Shuichi responded if at all. Shuichi treasures her final text message, and keeps it in his phone many months after Akemi's death.
How Akemi and Shuichi met in the manga is unknown, but in the anime, Shuichi Akai originally met Akemi by an intentional accident. She accidentally hit him with her car when he deliberately walked into the street in front of her in order to be hit by her. Akemi helped take him to the hospital, watching over him until he was better. When he woke up, he felt no anger over what she did, and even asked for her name, to which a very flustered Akemi replied, while he told her his fake name: Dai Moroboshi. After this they began dating.
When Shuichi meets Ran and Conan on the street, he comments on Ran's tears and tells her that she reminds him of a stupid woman (Akemi) who would cry behind his back.
Anime only (non-canon)
In the anime version of File 600, it is reveled that Akemi and Shuichi met because she hit him with the car. She quickly called for an ambulance and they took him to the hospital. In the hospital, they met and reveled each other their names, although Shuichi lies and told her his name was Dai Moroboshi. After it, they started meeting.
- Shuichi Akai's voice actor, Shuichi Ikeda, is the real-life husband of Akemi Miyano's voice actress, Sakiko Tamagawa.
- In an interview in Singapore in 2016, Gosho confirmed that Akai and Akemi are cousins. It is stated at 34:23 in the audio link.