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#//but yeah he's burned so many bridges and there aren't even ropes left on some for him to climb on
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I've been thinking (because I'm quarantined and bored, sorry )..how it could be possible for Jack to form a good friendship? ...I mean even if a person shows affection, good intentions or a real interest on his stuff... the chance of Jack's betrayal is still there. I don't know I'm wondering ..if he can have a healthy friendship.
*cackles*  Jack Spicer, as he is in XS, is not capable of forming a stable and healthy relationship, despite the fact that he desperately wants and needs one.  And if that ain’t the tragedy of the whole series.
The Jack of Showdown
Just when Jack finally starts to actually warm up and be open and honest about his feelings with others, he either gets grossly mistreated (“The Deep Freeze,” “The Apprentice”) or is presented with the choice of being loved and accepted, despite who he is and what he’s done, or giving in to his baser instincts and double crossing his new would-be friends to get praised by someone who could not care less about him (“The Apprentice”).  It’s difficult to tell if Jack feels he doesn’t deserve to be happy for some deep and personal reason, or if he’s so focused on being seen as EVIL™ and not good; that he believes he must take any and all opportunities to prove his evil worth.  Whatever the reason, the Jack in XS would need someone that will stick by his side no matter what decisions he makes, or what actions he takes to push that person away.  Someone who unconditionally supports him and wants to be by his side.  The problem is, that’s more of a pet and has the potential to become quite toxic.
The Jack of Chronicles
As for the Jack of XC, he has some boundaries, and he’s not quite as ruthless.  He knows he’s kind of a loser, but he still really wants a girlfriend to help boost his sense of masculine ego.  But more importantly, he just wants a friend, to the point that he was willing to pay people to hang out with him (just like in XS “Something Jermaine,” “Judging Omi” and XC’s “Magic Stallion and the Wild Wild West,” “Buddy Blue Ray and the Golden Bunnies,” and “Heal Me”).
Jack enjoys Wuya’s company, but she gets frustrated with his lack of action in favor of building capital or just having fun (the Golden Toilet arc, “Super Cow Patty,” “Tokyo Madness,” and “Omi Saves the Holidays” among many others).  Jack seems to have moved out of his parent’s basement, and is now in his own warehouse/factory, so he’s really trying to focus on starting up his Evil Business idea and often refers to himself as an “evil entrepreneur” throughout the series.  While Wuya appreciates the “go get ‘em” spirit, she still feels that Jack isn’t doing enough to help her, which is the whole reason they teamed up in the first place.  Because of her nagging attitude and matriarchal approach to the relationship, Jack often feels smothered and refuses to act.  However, he still has boundaries and refuses to do certain things if they are not in his interests as well (“Back in the Flesh Again”).
Jack and Shadow
With Wuya as Jack’s pseudo-mother, he needs a datemate to call his own.  Gone is his curiosity in Kimiko (though he does seem to think she’s still cool), but if it’s any other girl, he will do his best to impress her.
Case in point Willow--who he tried to ask on a date if he won the Showdown Trio in “The Fall of Xiaolin.”  She strongly states that she isn’t interested in him in the least, and because the two never see each other again, I would assume Jack dropped the pursuit.
Shadow on the other hand, he likely sees a lot of himself in her.  They’re both evil, admire Chase, they seem about the same age, and... that’s about where the similarities end.  Shadow’s actions say that she is repulsed by Jack, but she never pushes him away, and even praises his “doo-hickies” (“The Laws of Nature,” “Rocco”).  With the use of camera drones, Jack witnessed a lot of the private behavior and abuse between Chase and Shadow, and even some of the abuse in person ( “Tigress Woo,” “Rocco”).  Even the cold open of “Who Shrunk Master Fung?” features Jack being very careful not to harm a strange bird, who is later revealed to be Shadow.  Case in point, the Jack of XC has a streak of kindness in him, and it is unclear if Shadow sees that and resents Jack for having it, or if she admires that aspect of him.  Regardless, after the events of “The Laws of Nature,” where Jack effectively double crosses Chase (and her by extension), Shadow likely made the choice to never trust Jack completely.  She double crosses him at the end of their wonderful team up in “Back in the Flesh Again.”  And Jack doesn’t even get upset or angry about the loss and betrayal.  He’s even more smitten and tries to brag to Omi and Ping Pong before realizing they aren’t into it and flies off.
Overall Jack and Shadow have feasible grounds for a relationship--even a romantic one--if they could both create some honesty and trust between each other, but neither is willing to do that, despite Jack’s over sharing (literally every time he opens his mouth around Chase).  For further reading on Jack’s relationship with Shadow and Chase, check out this post.
Jack doesn’t interact with Tigress, Kimiko’s older sister, much, but he does bother to keep tabs on her and warns Kimiko about her sister’s more nefarious activities (“Tigress Woo”).  It’s unclear if he did this in an effort to get closer to the Monks as a friend, or if he was stalking Tigress because he was attracted to her.  In either case, Tigress is never seen again or mentioned by Jack.
Jack’s Other Interests
There are a handful of episodes in XC that revolve around Jack seeing or meeting another evil-doer and fixating on them, often trying to model himself after them in some fashion.  He does this with PandaBubba to a lesser extent in “Magic Stallion and the Wild Wild West,” then goes full blown fan for Super Cow Patty (in his self-titled episode) and later Le Mime in the same episode, making fan videos and full costumes with personas for both his fixations.  In both instances with the truly evil characters (PB and Le Mime), Jack was looking for a sense of acceptance by an Evil Businessman and entrepreneurial peer, and a sense of belonging to a larger community with Le Mime and his henchmen.  That desire for belonging to a larger community is reiterated earlier in the series with “Heal Me” and Reverse!Jack’s cult.
However, when presented with an actual fan of his, Tiny Sim, Jack is actually somewhat reluctant to have the fan tag along with him.  And maybe that was for the best, as Jack soon discovers that the fan he inspired to become Evil is actually a lot better at it than he, himself, is (“Drawn to be Evil”).  In retaliation, Jack confines the fan to being just a creative idea intern.  Jack is essentially taking credit for all of Tiny Sim’s ideas, and not paying the kid a thing.  Sim, either because he’s doing what his idol taught, or because he feels cheated, makes it a priority to take a Wu or two when he can out of Jack’s stash (“Mark of the Dragon Spirit”).  Sadly, the series ended before the relationship between these two could be further developed.  It wouldn’t have been healthy, but at least it would have been something.
Another important note, Jack does make the clear distinction in both series that the gallery of sellswords he pays to be around him are only in it as long as there’s money for them to be had.  They are not his friends, they will never be his true friends, they’re just people he pays until the money runs out (“Something Jermaine,” “Judging Omi”).  So Katnappe, Tubbimura, Cyclops (after their initial debut), and to a lesser extent Vlad will never truly be Jack’s friends.  Vlad does make a return in XS’s “The Demon Seed” to try and cheer Jack up (not that he’s very good at it), but he doesn’t seem to want anything from Jack other than to do evil things and pal around.  This is a bit of a departure from their first encounter where Jack was presumably paying Vlad to be his hired muscle and inside man (“The Deep Freeze”).
Jack’s Robots
Jack’s relationship with his various Jackbots and other robots is an interesting one.  It’s possible that he created them out of a sick sense of wanting to have friends that he could control, but it comes back more to how the bots are presented in both series.
The Jackbots of XS seem to have a hive mind of sorts, as they will blindly (and sometimes literally) follow their master’s commands.  Those that fall are replaced as if nothing happened to the fallen Jackbot; their numbers are legion.  The bots are later programmed with emotions and feel sadness, but not fear.  This is interesting, because Jack is shown having temper tantrums from time to time, but he doesn’t break things, only tosses them around (“The Journey of A Thousand Miles”).
Jack’s relationship with the more “custom” humanoid robots is split into a binary.  On the one side are the bots that went rogue and have tried to annihilate him or simply want nothing to do with him: Chameleon Bot, Robo!Jack, and the patent-pending Shen Gong Wu Detect-o-bot.  On the other side are the bots he grew very attached to: Yesbot, his Cheerbot squad, and the Shen Gong Wu Detect-o-bot before it went rogue.  Both Yes~ and Detect-o~ allow Jack to be more of a child, as he is depicted being held like a scared child with both of them (if I remember correctly.  “Oil in the Family,” “The Demon Seed”).  He treats them like the parent he doesn’t have around.  The Cheerbots are his hott Barbie dolls that he gets to dress up and maintain.  He doesn’t go much farther than projecting personalities and life problems onto them.  Eventually they are absorbed into the Jackbot hive.
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Remember how Jackbots don’t show or know fear in XS?  XC opens with Jack having a tantrum, and many of his various designs of bot run away from him.  Jack is left cornering Chefbot, who has darts sticking out of his chef’s hat.  Rather peculiar for robots to be afraid of their master, especially since they are meant to be hoards of drones.  As Chefbot is developed as a character, Jack comes to respect his creation more, but Chefbot says he has no interest in hanging around someone like Jack; he wants to go places and be a real chef!  He can’t do that if he’s making paltry snacks for Jack.  Chefbot’s last appearance in the series is on a cooking show (either on TV or YouLook) making pizza, while Jack follows along from his RV.  Jack seems quite relaxed and at ease, even using the Banyan Twister Shen Gong Wu to stretch his body and the pizza dough.  It is never stated, but perhaps Jack is proud of his creation accomplishing it’s dream.
Thank You for Being a Friend
In conclusion, the Jack of XS is incapable of having a healthy friendship with anyone, either because he thinks he doesn’t deserve it or because he really is just a terrible person and pushes everyone away.  He would need someone to stand by and support him no matter what he does and no matter how horribly he treats that person.  Such a relationship has the potential to become toxic if boundaries are not set and if Jack doesn’t grow as a person.
The Jack of XC is desperate for a single friend, but 98% of the cast sees him as a pathetic loser, and not worth a second of their time.  Those that do see value in Jack’s companionship have all been hurt by Jack’s betrayal and lack of trust, or have betrayed Jack, because they have no trust in him (often from a previous encounter).  For this Jack to form a stable friendship, he needs someone who he can talk to honestly, openly, and not be judged for his feelings, and he seems to want someone who talks the same way to him.  He’s ready for a relationship, he just doesn’t have the rapport or trust built up with anyone.
TL;DR
Jack lacks basic trust in all his relationships.  He would need someone he can constantly count on, while also setting healthy and reasonable boundaries with that person.  If honesty and trust--ABSOLUTE TRUST--is there, Jack can have a friend, maybe even something more.
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