#simple bob

Failboat & Bo:

Bo is Chat's godmother. Failboat was not initially planning to give anyone the title, but his fears regarding his own personal safety compelled him to put someone down for the job, and given that Bo was their primary caretaker for months before they met, and continued to be a pseudo-guardian figure to them, he decided she would be best fit for the job. This means that Erica is technically also Chat's godmother and Failboat rubs this fact in her face quite often.

Unrelated to this, Failboat holds a lot of admiration for Bo for her vampire transformation, he still has complicated feelings about the catsuit debacle and really respects how unapologetically true to herself she became, after seemingly also being trapped in her Job. Simple Bob & Big Bill:

Adjective name buddies! This is what would get them talking if they were to ever meet, Bob's never met a non-Warrior who goes by a title like Bill's in their day-to-day life. He holds a lot of respect for Mages, he initially travelled with one when Dark Lord Hank first attacked Greenhorne, and he idolises the Great Sages. In fact, following their conversation and knowing for certain how dedicated Bill is to using his magic for the good of those around him, he believes the duck to be a great candidate for the next Sage. Smuk & Failboat:

Smuk genuinely did go through an "exclusively cooking vegetarian and vegan options" phase post-S1, in which he travelled to the Realm of the Fey and studied the methods of a village known for its plant-person population. He was inspired to do this not by Pirahnyawn, but by Failboat, the biggest fan of his HP Banana Fritters, his words of encouragement giving Smuk the idea to pursue healthier options.

(In fact, this was a general trend for former travellers in the Dark Lord's era, a diet of whatever the monsters dropped was generally incredibly unhealthy, and the most common of them - such as goblin ham - became detestable to most after too much consumption.) Erica & Lanc:

Erica has assisted various incompetent royal and royal-adjacent warriors in her lifetime, the Prince from a Nearby Land being only one of many examples of such a person. As such, she became well-acquainted with the names and histories of most royal families in Miitopia, including that of the Caurde family ruling the Powdered Peaks. "Prince Lanc" has never slipped past her tongue, nor has "Princess Lanc", but the title was on her mind for a while after their first meeting, however much she held it back for the sake of respect. Deko & Chi:

For a period of a few months he is incredibly reluctant to look back on, Deko tried to launch a career in metal music during the Three-Year Gap, specifically during the first year where he had absolutely no idea what he was doing with his life post-failed experiment and post-FailFleet Miis. He titled his first and only song "Ignite!", inspired by Chi's love of fire, and Lanc's technique of igniting his spear. Even as he was partaking in it, Deko was too embarrassed by the ordeal to properly promote himself, so the song got no traction and the only like it has on any streaming service is Chi's, who habitually searches for any fire-related music in existence and formerly searched her friends' names almost as much. She sets the song as her ringtone only when she's planning to meet up with Deko, for the fun of it. Chi & Chat:

Chaos duo, property damage charges would be off the charts if they were ever actually prosecuted. Chi thinks Chat's Tank features are really useful for scientific experiments, and by that, she means she's tinkered with their cannon in every way she can think of and accidentally blasted several Inn walls in the process. Her most successful outing was fitting a flamethrower to Chat's head, which they immediately burned down a nearby tree with, proving to Chi that testing these things outside doesn't lead to much safer results.

Also she once used their conveyer-wheel-things to ride across the walls and ceiling of an Inn, she hasn't recaptured the magic since and not even Chat knows how she did it. Lanc & Deko:

Lanc's always secretly wondered if they could configure something science-y that could reverse Deko's failed experiment. They don't actually know anything about surgery, especially not the weird Peculia stuff Deko went through to be stuck with permanent Imp status, but they figured they might be able to work something out with their Glitch technique. Eventually, Deko caught them drafting an idea, and persuaded them to stop, not wanting to go through any kind of experiment like that again, even a reversal. Rose & Shrimp:

You think Shrimp cosplays? I think Shrimp cosplays. Regardless, Shrimp is well-known to have an extremely dedicated fanbase, who may not always see the real person beneath the streamer, and is less well-known but still known to have had a rough childhood of not being seen for her real passions. It's entirely possible Rose would see this young girl, either on social media through her world-saving fame or streaming career, or by visiting The Incident, and feel a twinge of sympathy for the constant smiley persona hiding social trauma. But they could definitely also just bond over cosplaying, or fashion in general, Rose may be interested in a goth outfit like Shrimp's. Petunyawn & Orion:

Orion was initially concerned when Slapo brought home another clearly very young child she'd apparently been stringing along to a lot of her very dangerous adventures, but his concern in that regard quickly faded into the background when Petunyawn's mouth opened, again and again, asking whether she can roll down the stairs or eat their potted plant's gravel or hang half her body out of an elevated window, all suggestions of Slapo's which she did seem hesitant about, but seriously considered anyway. Her understanding of basic safety and social rules were shot because of her neglectful father, and Orion soon began spending every moment he has with her trying to teach her about the world.

Joker & Erica:

Joker was generally very nervous and unhopeful about TFFM's competency, knowing he wasn't a particularly skilled fighter and not trusting Failboat's impulsivity, Rose's even greater nervousness, or Pirahnyawn's despondency. He felt ostracised from the party, disappearing from every other fight and not bonding much with his adult teammates, but in the few one-on-one interactions he ever had with Erica, she empathised with his lack of enthusiasm, being extremely concerned with the haphazardness of the party in her early days of membership. Due to her bonding with the team, though, she was actually more optimistic by this point than Joker was. Mar & Smuk:

The respective Chefs, they'd quite obviously have a lot to bond over in that regard, but that's not all that strongly ties these two. Smuk and his trusty frying pan dealt the final blow to Mar in his Darkest Lord form, a move Mar performed himself to finish off Hank, and that makes me wonder how significant of a memory that final attack was for Mar. The fact that Smuk even did it holds an uplifting moral - Erica complained about him rushing in to attack too much when she first met him, but it's that determined personal style that ended up saving the world. I think Mar very well could've found it resonant that he was taken down by a man driven by his passions, having severe enough issues with his own identity or lack thereof, and found himself drawn towards the talent of a Chef as a result. Orion & Joker:

Orion was actually well-acquainted with Mr. Amamiya, his young daughter is only a few years older than Slapo and the two fathers had repeatedly met during parents' evenings and the like at their school in Greenhorne, not to mention the Amamiya Merchant Family being one of the more successful independent businesses in the entire Travellers' Hub. Ren Amamiya was temporarily running the shop one day when Orion decided to visit, and seeing a familiar face from old photos of Chi's sparked his interest, plus the usual vaguely paternal concern. He promised not to speak about Joker's true identity, but he also promised that at least one old friend of his would be especially delighted to see him again, if he should feel up to it. Friend & Petunyawn:

Friend isn't proud of their short fuse, it's mainly a leftover from Lee's aggression and her own similarly aggressive coping mechanisms, but Petunyawn's doubts regarding anything and everything are a sore reminder for him, of the living embodiment of intrusive thoughts that was Lee and the self-destructive places their mind drifted to following his departure. They've also been somewhat inexperienced with children throughout most of her life, carrying a friendly smile and a mostly gentle demeanour but lacking a filter in the words out of his mouth. She eventually comes to relate to Petun in this respect, recognising her impatience and brutal honesty as a humane, forgivable flaw, and appreciating her curious mind. They find value in showing her the wonders of the world she's missed. Shrimp & Friend:

Friend is Shrimp's usual roommate post-S2! She always admired them for his dedication for bringing light to the world, and attentiveness to the group even as their mind deteriorated from Lee's influence. She didn't recognise that at the time, of course, she just saw Lee as an extension of Friend's goofier unhinged side, and after the truth came out, she felt a compulsion to aid her in realising themselves, though she didn't get many opportunities due to Friend's self-isolation. Post-S2, though, Shrimp takes the chance to finally properly bond with them over his newfound fixation on fashion and design, and their inherent connection of endless smiling and therapy avoidance made them a good pair of roommates, Shrimp carries the energy Friend often feels drained of and Friend carries the maturity and experience Shrimp lacks, while also being a slightly more permissive authority than the already soft-hearted Orion, better for day-to-day antics and ranting. Bo & Simple Bob: Bo currently defines herself by her newfound cool confidence. For too long, she buried herself under an extremely thin pretence of regality and an all-too-real pretence of nervousness, two traits that served to isolate herself, one through glorification and the other just through social incompetence. Simple Bob isn't unfamiliar with either, Warriors go hand-in-hand with royal escorting, and any nervousness he may feel in his life is very thoroughly buried under his own cool confidence, the one trait he's immediately recognisable for despite his title. He presents as an extremely honest and collected person, a frankly idyllic image for Bo that she'd be somewhat enamoured with if they were to ever met, especially in his moments where he's actually honest about his own complexity, his struggles with forming meaningful social connections and doing anything for himself rather than to show off for others. Bo knows those, and it'd be nice for her to see Bob getting by despite these afflictions. Chat & Mar:

Mar's never known what to do with Chat, and they're well-aware of that. He's technically been their temporary guardian for longer, and more officially, than Bo, but their shared emotional volatility always made them a tumultuous duo, Chat being against voices of reason by their very nature and Mar not even being a reasonable enough voice to counteract them. Chat does really like Mar, he's a charming and capable leader, and always ensures he makes enough food for their extra mouths during dinner, but they find it incredibly difficult to imagine a world where he parents them, like they can for almost every other adult in their life. That changes a little when they learn that Mar's vengefulness over their injuries in the final battle drove him to finish Hank off, showing an emotional connection with them they'd otherwise sometimes struggled to read in him. Big Bill & Rose:

Huh, don't think I've thought about this dynamic even once in the nearly four years I've had this special interest. Time to challenge myself, I suppose!

There's something to be said about how both of these two look down on people. Rose gains a superiority complex, compensating for her insecurities about being peer-pressured into stealing an innocent woman's identity by relishing in the power that comes with the position, while Bill is exclusively focused on the well-being of those in rougher circumstances than him, throwing away all his plans just to help a random girl he sees being bullied below the water, while Rose threw away all her plans to take from a random woman and gain the power of the stars. Bill developed magical powers as well, but for the comically simple purpose of performing pyrotechnics for his new pseudo-little-sister's performances, on top of saving the world and all. If he were to meet Rose, and learn about her history, I think he'd understand her magical drive, but would be concerned about her motives and the consequences of her actions, hoping she comes to recognise the value in the simple life she wanted to start with.