Hey slug, i was of the mind that nothing about ramudas cute self is real and it’s all just a cover for chuoku, but when the Catch Us If You Can drama track came out, I second guessed that a bit because ramuda is still shown to be using his cute voice around gentaro and claims it’s for positivity. Do you think that there’s some truth to the mask he wears? Or is he just using his cute self to cope with the horrible situation he’s in? does he think playing his role as the cute one provides comfort?
Hmm... at the risk of putting in too much headcanoning I think this is partially out of habit and partially, as you say, out of comfort.
In terms of who Ramuda truly is, I think his mask/exterior personality is partially reflective of who he is and also partially not. It's hard for us readers to draw the line (and it's probably hard for Ramuda as well) because he's worn this disguise for so long, so it's ingrained in him. Ramuda's inner personality has very different ways of expressing dissatisfaction (anger, crying, smoking) than his exterior personality (exaggerated moping) because both interior Ramuda, aka Ramuda by himself, and exterior Ramuda, aka Ramuda around other people, both deal with quite a lot of crap worth being upset over. But even when Ramuda's being true to himself, like when Fling Posse defends him in the end of Marionette, he expresses happiness in the same way that his exterior self does (laughter, physical affection, claims of "We're a posse!"). While Ramuda has a lot of experience being grumpy on his own, he has virtually none of being happy. So, in unfamiliar situations like this one, it's probably easiest to default to how the exterior personality would act. In time, Ramuda may develop his own methods of self-expression without the influence of the exterior personality, but he may also continue to adopt them in the future. Some aspects of his personality are almost certainly just for show (like playing dumb) and will probably be dropped or modified in time, but Ramuda seems to have grown into others. For example, he definitely enjoys hanging out with his friends, even though this was probably, at first, an excuse to keep a closer eye on the people he was spying on for Chuuouku.
In terms of comfort and coping, I don't know if this fake role necessarily provides him comfort, but there's a definite argument to be made that using his real voice around other people is distinctly uncomfortable. The first time Ramuda's disguise slips is in TDD 9, where Ramuda yells at Jakurai for calling him artificial. This distresses Ramuda to the point where he begins insulting and punching himself (granted, this is done exaggeratedly playfully, but judging by his facial expressions, it's not a completely fake reaction) before Jakurai stops him. Ramuda doesn't use his real voice again until Jakurai confronts him about putting Yotsutsuji in a coma, which in the end is even more distressing to Ramuda. I've been thinking a lot recently about how badly Ramuda internalizes this and refuses to process it, as he doesn't ever comment on this directly in main canon. But he does take much, much longer to warm up to Fling Posse than he did to befriend Jakurai. Compare how physical Ramuda gets with Jakurai starting right after they met (TDD chapter 7 is a good example of this, taking place almost immediately after Jakurai returned to Japan from overseas) and how long it takes for Ramuda to start hugging Fling Posse (FP/M 14, after the first DRB). Also up for consideration is a line from FP/M+ 10 (Marionette) where Ramuda admits "I always feel like I'm going to be abandoned at any moment." Having Ramuda's first friendship blow up in his face shortly after this friend found out who Ramuda really was, deep down, makes Ramuda more frightened than ever of revealing his true self. Noting also how he is ridiculed and disregarded for his emotions, it becomes more compelling than ever for Ramuda to hide himself when others are around. Because of that, even though Ramuda trusts Gentarou and Dice more than anyone else in the series, I wouldn't be surprised at all if Ramuda still had reservations with using his true voice around them all of the time. He has a lot of damage he needs to recover from, and that takes time.