I love to think that Bruce, although he was never good at expressing affection, he could never see Dick sad, he would immediately jump into bat-dad mode.
Dick was a very expressive child. He could bottle up his emotions like Robin, sure... But Dick Grayson rarely needed to hide what he felt. Plus, Dick knows Bruce's social skills are atrophied, so openly expressing his feelings was helpful for him and Bruce (and Alfred, too).
However, when something he considered trivial bothered him, he preferred to keep it to himself. He usually managed to hide it until he was ready to talk about it... But sometimes he never really felt ready to bring up the topic himself.
And Bruce, even though he may not know everything about emotions, is a great detective, isn't he? He can definitely tell when something is wrong with his child. (It's a little hard not to notice when Dick has already started to shift uncomfortably on his feet, but although he doesn't let his body stay still, he doesn't say a word, when it is usually the little ray of sunshine that fills the space with conversations or random data on any topic).
Bruce always tries to help Dick in his own way, especially when he realizes that those "unimportant" issues are indeed important and he can now take matters into his own hands.
Even as an adult, Dick, although he now hides his annoyance much better, still has some nervous tics that Bruce has memorized and sets off his alarms, they are so subtle, and yet only seen when he is around someone he trusts... So, even when Dick is completely capable of figuring things out on his own... Bruce goes into concerned dad mode, ready to do whatever he can for his son.
(Yes, Dick knows this... Yes, there were times when he took advantage of this like Robin...)
(Yes, being the baby of the Justice League, it wasn't just Batman who went into protective mode when the little ray of sunshine looked nervous).