character relationship page
The following is an account of established relationships Sai has at damned. Because he interacts with so many people on a regular basis, this is mostly a list of those who've had some sort of impact on him. Don't be insulted if your character spent a lunch with him and isn't mentioned here.
Since Sai fails on connecting much emotionally, people are listed by the general feel he gets for them.
positive
Uzumaki Naruto (idkmybfframen)
Probably Sai's best friend from his own world. He was the one that broke Sai's emotionless barrier, and Sai would do a lot to protect him without thinking about it. He still has a folder with information on the first incarnation of Naruto he met at Landels (tte_bayo). This is also the third version of him that he's seen at Landel's (the second being whirlingwinds).
Uchiha Sasuke (sasuke_of_sound)
Despite the boy's overall attitude, and the fact that they've been at each other's throats more than once since they arrived, Sai harbors no bad feelings towards Sasuke. The missing-nin is still willing to work with him on a regular basis, and then there are Naruto and Sakura's feelings to consider...
Haruno Sakura (see_my_back)
A teammate, Sai often ends up saying just the wrong thing around her. Despite this, she remains a friend. Though he remembers another incarnation of Sakura at Landels before her (she_bloomed), the current one has had more influence.
Nara Shikamaru (toobothersome)
Sai's positive opinion on Shikamaru stems mostly from the fact that he's a fellow Leaf Ninja. They work together well enough due to their mutual ability to stay cool-headed. During their stay here, they've gotten to know each other perhaps a little better than they would have liked, given troubling circumstances.
Sechs (sixth_attack)
Sechs is Sai's new roommate, and he isn't quite sure what to think of him. Their first meeting involved Sechs being brainwashed, though he doesn't hold it against him, and apparently the man is partly mechanical, which the ninja finds difficult to take in.
neutral
Malcom (Mello) (swornandbroken)
Sai knew Mello when he was in the Institute before (cnflctofintrst) and they were allies of a sort. Though he approached the man again upon finding him back at Landel's, they aren't off to the best of re-starts.
Okita Souji (notachick)
They've only spoken a couple times, but Okita sat with Sai and gave him advice when he needed it the most. The ninja still has the drawing Okita made tucked safely away in his dresser. He considered the man a friend, but unfortunate circumstances led Sai to killing Ayumu, a woman from Okita's world, and the latter has attempted to kill him more than one time since.
negative
Hanabusa Aidou (blood_and_pocky)
Sai doesn't hate Aidou, but the boy says things that confuse the hell out of him, and his relationship with Sasuke is questionable at best. He will avoid him on principle, as questioning him has gotten him nowhere.
memories
these are characters that have been dropped, but who still left an impression
Kurikara RyuOh (hotlittledragon) - Sai's first roommate. The two of them didn't have much issue with each other, though Sai chastised him on multiple instances for getting sedated.
Jack Horner (i_slay_giants) - The first patient Sai met at Landel's, he ended up getting stuck in the middle of his dealings with Usopp. The ninja had no real opinion on him, but was sometimes just shy of stabbing him if it looked like he'd be threatening his pirate friend.
Uchiha Itachi (youlackmascara) - Sasuke's brother and an Enemy of the Leaf Village. Sai's insistence on forming an alliance with the man put him on bad terms with Sasuke, but not beyond working with him.
Monkey D. Luffy (rubbermancan) - Usopp's captain, Sai first met Luffy when the two pirates were following a radio clue to a bathroom full of giant leeches. You don't come out of a situation like that without forming some kind of bond with the other involved parties.
Hatake Kakashi (lostonlifesroad) - Kakashi is the leader of team 7 (or Team Kakashi, when Yamato isn't in charge). As such, Sai looked to him for leadership while in Landel's... granted he could find him. He was there once before (raptscarecrow), but not for very long.
Jiraiya (toadally4boobs) - As one of the Sannin of the Leaf Village, Jiraiya gets instant respect from most ninja, and Sai is no exception. Add in the fact that he's Naruto's teacher. Though Kakashi is Sai's leader and any important information was generally taken to him first, Jiraiya also held a position of authority.
Haninozuka Mitsukuni (host_club_honey) - "Honey" was Sai's previous roommate. He had a penchant for sweets, to the point where the ninja would generally end up handing over his desserts at dinner time. They got along fairly well. Though Honey has mentioned having some combat ability, Sai never got to witness it.
Usopp (usoppsenchou) - Usopp was the first friend Sai really made at Landel's. Many of his nights were spent working with the pirate, and if they weren't he usually checked up on him first. He returned shortly, and though he didn't remember Sai, the ninja tried to recreate that bond. Unfortunately, he has since disappeared a second time.
Haku (faithful_frost) - Haku had been around since before Sai arrived. The two of them had a shaky alliance (as the mist nin would have nothing to do with Sasuke) and got together only on occasion to neutrally discuss matters of the Institute.
Artemis Fowl II (byname_bynature) - Apparently a friend of Haku's, Sai ran into Artemis a couple times... usually in the shower and with the result of embarrassing the poor boy something fierce. Clueless to this, Sai found the kid mildly interesting and attempted to help him on more than one occasion.
Morinozuka Takashi (mukuchi) - "Mori" is Honey's cousin, and the two passed each other occasionally as Sai was leaving for the evening. They talked once or twice, and Sai doesn't think poorly of him, but aside from that they didn't have much contact.