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second baby 5 ship in a row! she's one of my favorites so i love giving her partners she can be obsessed with </3 as i said before, nothing wrong with sai x baby 5, i just prefer a different dynamic when it comes to baby 5 ships!
baby 5 and bart aren't as random as some of my other rarepairs, since they were together in dressrosa. it's such a shame we never got the chance to see them interacting :( they could have had a really fun dynamic... imagine baby 5 falling in love at first sight with bart, while he's so weirded out by it at first, but then becomes kind of intrigued. ohhh i'm so not normal about them. i'm sorry
we know baby 5's taste in men is peculiar to say the least, so bartolomeo could be a perfect target for her attention. maybe while they were dealing with doflamingo's birdcage bart shot baby 5 a compliment, not thinking much of it, and she absolutely fell for him. and then baby 5's usual shenanigans ensued. like, her telling him how he's so sweet and respectful and they should get married, while bartolomeo doesn't get any of it and is just so confused because he's not used to this type of attention at all... but then he warms up to her and starts telling her about his love for the strawhats and how he's so excited about finally meeting them in person (in true unfiltered autism fashion), and baby 5 just listens to him so attentively because she finds this side of him very endearing...
i love the idea of them together because they're just two people that are both seen as "weird" by society, even though the only unusual thing about them is that they have developed a way of showing their love that is so unfiltered and passionate in response to their difficult and traumatic past. even though they don't look like it at first glance, they share many similarities. they could have worked really well together in canon, too: the developing of their relationship could have been a breeding ground for many funny gags. oda you really fumbled the bag this time