ποσάκις

Matthew 18:21 ποσάκις how often

Then Peter came to Jesus and asked, “Lord, how many times shall I forgive my brother who sins against me? Up to seven times?”

Here: Asks for a number. Peter wants to know how many times he has to forgive, which assumes there is a point where he may stop.

Matthew 23:37 ποσάκις How often

O Jerusalem, Jerusalem, who kills the prophets and stones those sent to her, how often I have longed to gather your children together, as a hen gathers her chicks under her wings, but you were unwilling!

Here: An exclamation, not a question asking for a number: 'how many times!' It stresses how many times he tried and was turned away.

Luke 13:34 ποσάκις how often

O Jerusalem, Jerusalem, who kills the prophets and stones those sent to her, how often I have longed to gather your children together as a hen gathers her chicks under her wings, but you were unwilling!

Here: An exclamation, not a question asking for a number: 'how many times!' It points to repeated attempts. Exactly which attempts is debated (see debates).