John 16:23

The context indicates that the day in view is the time when the disciples’ joy would have become full. That would be after Jesus’ resurrection and ascension (cf. Luke 24:50-53). The disciples would ask Him no questions then because He would be bodily absent from them. They would have to request answers to their questions from the Father in prayer (cf. Acts 1:14).

Jesus encouraged the disciples to ask the Father for whatever they needed, however. He did this by repeating His promise that the Father would grant petitions that they would offer "in Jesus’ name" (cf. John 14:13-14; John 15:16).

Some commentators made much of the two different Greek words for asking in this verse. The first one that occurs, erotao, usually means to ask a question, whereas the second one, aiteo, means to ask for something. However, John often used erotao to describe asking for something (John 4:31; John 4:40; John 4:47; John 14:16; John 16:26; John 17:9). Consequently we should probably not make too much of this difference. John frequently used synonyms with no great distinction in mind.