Most of the pairings that came about at the tail end of Naruto made sense. In the cases of Temari and Shikamaru and Naruto and Hinata, for example, they were relationships that blossomed at long last. The same can't be said of Sai and Ino, who felt like a strange couple because they didn't get much development together on screen.
While Ino checks some of the boxes that Sai would want in a girl, there wasn't enough on-screen growth to make it feel natural. There are far better fits in the rest of the anime world.
10 Kongo Mitsuko From Scientific Railgun Has The Confident Personality Sai Needs
Kongo Mitsuko from Scientific Railgun has a personality somewhat similar to Ino's. She's very confident both in herself and in her appearance. She isn't above showing off her figure, nor is she shy with her words.
Both of those are traits that Sai would need in a partner, considering he can be more than a little dense at times. They'd also be able to grow together as Kongo struggles with common everyday things in a similar way that Sai does with emotions.
9 Izumo Kamiki From Blue Exorcist Went Through Similar Experiences As Sai
One thing deeply ingrained in Sai's character is how his upbringing affected his mental state. His training with Root forced him to suppress his emotions, something that Izumo went through while in isolation during Blue Exorcist. Both of them have had similar experiences, meaning they could help each other break out of their colder personas. And Sai's bluntness paired with Izumo's insecurities would certainly lead to more than a few comedic moments.
8 Erina From Food Wars Is As Dense As Sai Is With Relationships
Erina resembles Ino in terms of appearance, from her blond hair to her attractiveness. Their personalities don't have much overlap, though; Erina is more of a haughty noble type, which might grate on Sai at first.
But if he could get past that demeanor, he'd find a girl who's as dense about relationships as he is. She may even know less about them than he does, since she needs to use shojo manga as a research tool. The two of them would make a cute pretty boy-and-girl couple.
7 Kaname Chidori From Full Metal Panic Is The Perfect Tsundere For Sai
Tsundere characters aren't for everyone, and at times, they're downright abusive rather than just having an aggressive personality. Kaname teeters on that line, showing a mix of care and overly aggressive tendencies.
In many ways, she's the exact opposite of Sai, as she's unable to control her emotions. The two characters would make for an interesting mix: Kaname teaching Sai it's okay to be emotional and Sai teaching her how to ease her anger.
6 Kaguya From Kaguya-Sama: Love Is War Has The Intelligence That Sai Would Find Fascinating
Kaguya has a level of intelligence that would draw Sai in, enhancing the interest he already has in growing his emotions. His cold and distant personality would draw her in, in turn, and she'd want to discover what made him that way.
Their two personalities would mesh well together, except it would require one of them to make the first move, something Kaguya isn't good at. Sai may be the type to do so, but he isn't one to pick up on subtle hints.
5 Diana Cavendish From Little Witch Academia Has A Seriousness & Composure That Matches Sai's
While Diana at first seems like the typical queen bee character in Little Witch Academia, she has far more depth than that. She's rude towards other students not out of superiority, but out of genuine frustration that they aren't as good at magic as she feels they ought to be.
While she's confident in herself, she isn't arrogant in the least, always admitting her mistakes and vowing to get better. It's the type of composure and serious nature that would match Sai's own deadpan demeanor.
4 One Piece's Boa Hancock Would Fall For Sai's Immunity To Her Charms
Much like Luffy in One Piece, Sai would be immune to Hancock's charm, forcing her to feel rejection yet again. While Sai isn't quite as blasé towards women as Luffy is, he doesn't view them in a typical way for a man. This atypical approach would help break down the façade she'd built, revealing a woman Sai would have an interest in. Beneath her arrogance and vanity is a sensitive and vulnerable woman, and those two traits are ones Sai could nurture in his more adult state once he grew more accustomed to expressing his emotions.
3 Touka Ryumonbuchi From Saki Has A Nurturing Attitude A Younger Sai Needs
On the exterior, Touka is as eccentric as she is lady-like. She enjoys the finer things and the attention that they bring, and while she hates when others stand out more than she does, she can still be a very caring individual. When she takes a liking to someone, as she would with Sai, she can be very nurturing, almost motherly. That's exactly the type of attitude that Sai would need, particularly after Naruto starts to open his eyes to the value of compassion.
2 Fatina From Tower Of Druaga Has A Strong Sense Of Duty & Compassion
Fatina is more than a little vain and isn't above teasing those around her, something the Naruto version of Sai needs. The teasing would help him better understand his emotions, and Fatina's compassion for her friends would help him understand camaraderie, much like Naruto showed him. Her sense of duty would also give them common ground, as that's something Sai believed in fully during his time in Root. Her vanity could even teach him beauty in the same way Ino's did.
1 Sai Would Get Ami From Toradora To Reveal Her True Self
While Sai can be dense at times and fail to understand simple social queues, he isn't stupid. He'd be able to see past the facade that Ami put out there to manipulate others. This would likely lead to a tense relationship at first, much as Ami's relationship with Taiga was, but over time, the two would grow together and overcome the faults they each have. They'd both be there to push each other, becoming better people because of it.