
Lin F. answered 10/27/19
Avid Japanese Learner
Both words can be used to express that someone is asking for or requesting something, but in terms of tone and context, they're completely different.
In my opinion, "wheedling" has a slightly more negative implication to it, like the speaker or the speaker's intentions are persistent, annoying, or sleazy. "Pleading," on the other hand, gives the impression that the speaker is desperate or feels like/is the victim of something they don't deserve or is unjust.