Conan Edogawa and Ai Haibara
Sometimes everyone thinks both Conan and Ai have a special relation and friendship that nobody would understand. This is particularly true for members of the Detective Boys who often try to question their relationship.
Relationship analysis
In some episodes and manga chapters, Ai would give hints to Conan about her feelings towards him. But in the end, she would always tell him that she was just joking.
Conan tries to protect and save Haibara if anything happens to her. For example, during The Mysterious Passenger episodes, where Haibara stayed in the bus that had a bomb in it (to commit suicide because she was afraid of her future, and having to ever face the Black Organization,) Conan immediately saved her and told her to accept fate and never turn back.
Some fans can make parallels of Conan and Ai's relationship with that of Sherlock Holmes and Irene Adlers. Much like how Conan nor Ai say they actually "love" each other; Sherlock Holmes's "love" for Irene Adler is never directly stated. Sherlock Holmes, according to Watson, "respects" Irene Adler; like how Conan seems to 'respect' Ai (in a way). There is also the fact that Irene Adler was the only woman ever to have bested Holmes-- in all of the episodes of Detective Conan, it seems there is never a woman (or person, for that matter) to have outwitted Conan/Shinichi-- you could say Ai, has come the closest, with her and Conan being of the same level of intelligence, and during episode 411, Ai and Dr. Agasa come up with a riddle for the Detective Boys, and it seems Conan can't figure it out (for he lacks the motivation), and Ai seems particulary pleased about it. But Conan eventually figures the riddle out; though for a bit, Ai had "bested" Conan.
Conan/Ai moments
(Episode 129) - "The Girl From the Black Organization and the University Professor Murder Case"
Upon Ai's arrival at Teitan Elementary School, Genta eagerly offers the seat next to him for her to sit in. But as Ai walks towards the desks, she brushes right past Genta and takes the empty seat next to Conan, and in monotone says to him: "Nice to meet you." Shocking Conan, the only thing he can manage to say is: "Yeah..."
After class is over, the Detective Boys try to catch up with Ai in the hallway, wanting to ask her to walk home with them. Ai ignores all of Ayumi's attempts to talk to her until she inquires about her address, to which she replies: "22 Beika Block, Second Street." Conan regards the address as familiar and remarks to himself that her house can't be too far away from where his is. Ai then looks over her shoulder and smirks at him, again shocking Conan and causing a small blush to appear right above his nose. Genta notices and asks him if he "likes that stuck-up woman". Which Conan quickly denies.
When Ayumi and Mitsuhiko are telling Ai about the Detective Boys, she asks if "Edogawa-kun is in it too?". Shortly after, the Detective Boys come across a case, where a fellow classmate's older brother has been missing and wants to find him.
After solving said case, and Ai fires a gun through a window, causing her to get a scolding from Megure-keibu, and fake-crying (impressively well) to get out of it, Conan walks Ai back home to her house, where she is still crying. When Conan drops her off nearby her home, Ai immediatley stops crying and then brings about a drug called "APTX 4869". Conan is confused, as Ai continues to ramble about the drug, how he took it, and how she did also. It is apparent that Ai isn't just your average little girl. It is not until Ai tells Conan that she's occupied the Professor's house and that he's "not in this world anymore", that Conan begins to freak out. He tries to call the Professor but does not get an answer, while Ai smirks evily in the background (she's got the upperhand, at the moment). Conan then leaves Ai behind and sprints to the Professor's house, hoping to find him safe.
Later on, Conan, Ai and the Professor come across another case. One involving the locked-room-murder of a University Professor. After Conan solves the case, the Professor and Conan decide to head back home. When Conan gestures for Ai to come along, we see a tear roll down her face as she asks why he didn't help her sister. To answer a confused Conan's face, Ai explains (still in tears) that Hirota Misami was a fake name her sister took from the now-deceased University Professor, and Conan realizes that the same girl (from the previous episode)who died during the one-billion-yen robbery case. And Ai continues to shout at a stunned Conan, with all his deducing skills, he should've been able to see right through her sister's case. Ai breaks down and falls on her knees in front of Conan and clutches his shirt and continues to cry into it. The unfeeling boy, unlike a normal sympathetic human being, denies the very-teary Ai Haibara clutching onto him like she was his only life line (in a way, he was) the hug she very well deserved. But Conan silently thinks to himself: "This is probably the first true face she's ever showed me."
Episode 130-131
Near the end of the second part of this case, Ai stares off into the distance after conan made a joke about her being 86 years old. She tells him "I'm only eighteen, about a year older than you. Maybe someday..." before she stares off into the distance again.
Episode 136-137
Conan Edogawa gets lost in a castle where the Detective Boys are staying at and when every one tries to look for him it starts raining. Ai tells Ayumi to stop crying and that "Edogawa-kun isn't the type to make you worry. He'll come back himself." then comments on Ayumi's bag and about not letting her tears enter it. Ayumi replies, "Hey how do you know Conan-kun so well..." Ai replies, "Come on. Why do you ask?" "Is it because you like him, right?" Ai, surprised but recovers, asks, "What if I do?" Ayumi replies, "Then...I'm in trouble..." implying that there will be a love triangle if she does. Ai sees Ayumi is worried and does not want to mess with her anymore and plainly states she does not have those kinds of feelings for him.
Episode 138-139
At the start of the second Gomera movie, Ayumi falls asleep and puts her head on Conan's shoulder. When Conan turns to Ai saying he needs to use the restroom and asks her if she would switch seats, she puts her head on Conan's shoulder too, having fallen asleep as well.
Episode 230
Ai was petrified because she felt a familiar and scary presence around (most likely attributed to undercover Jodie Starling who is at the time that teacher). As a result, she wanted to stay on the bus and let go of life as she felt she would always put other people in her surroundings in danger. But Conan came back to save her by grabbing her and jumping out of the bus before it exploded. Jodie Starling said he looked like James Bond.
Episode 335-336
In episode 335, Conan's mother, Yukiko, tells him that he seems to be popular with girls.[1] Conan then asks if she's talking about Ayumi and she replies saying that not only her but Ai too. "She's looked your way about 10 times already." she says and continues: "There's only two reasons for a girl to look at a boy like that: he has something on his face or she likes him". Conan later tests Haibara by asking her if he has something on his face (while sleeping with the Detective Boys on the same bed). She then responds with a confused and bewildered look.
Episode 509
In a scene, Ai wants to know who Conan was talking to on his phone (she thinks it was the FBI). Conan says back, "It's not like a case (jiken) happened or something..." Ayumi eavesdrops and says surprisingly, "It's a affair (jiken)! A affair between Conan-kun and Ai-chan!?" Since jiken could also mean affair. They stared at Ayumi with bewildered and surprised faces.
Movie 4
Ai admitted that she wanted to forget about everything and always be with Conan "forever, just like this", shocking him. However, she immediately said she was joking.
OVA 9
After Conan swallowed the antidote of APTX 4869, he ran over to Teitan High School, and found that everyone had grown ten years older. When he saw Haibara, he grabbed her hand, dragged her outside and pinned her down on a tree for questions.