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Luke 18:8b However, when the Son of Man comes, will he find faith on the earth?"

Was Jesus being pessimistic when he said that? How would you answer this question from Jesus?

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Jesus never emitted personal opinions, so being pessimistic (or not) isn't a factor. Rather, all His questions are meant to address a particular topic which needs to be focused on. (See for example Mark 9.33,34 where Jesus asks the disciples a seemingly random/insignificant question only to enter the topic the disciples were discussing privately earlier; or John 8.5, where Jesus is specifically asked for an opinion, and refuses to give one at all because it's not required in order to address the topic.)

The question about faith isn't as much a question as it is a call to introspection, inviting Jesus' followers to be on a constant lookout whether they still have enough faith for when He returns, since, among others, salvation (see Rom 5.1,2 vs Rom 11.20) and even survival until then (see Heb 10.38a and Rom 1.17b) depend on having faith.

To complete the picture, the start of the section frames how this question fits at the end of the parable of the unjust judge:

Then Jesus told his disciples a parable to show them that they should always pray and not give up (Luke 18.1, NIV)

So, putting it all together, Jesus is saying: "you must pray and not give up; but, will you be able to do so with faith until the end? (i.e., watch out for this growing problem)"

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I think Jesus meant that as the woman in the parable who never tired of asking the corrupt judge for justice, when he turns towards us will he find the faith with which we receive what he gives us?

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