Questions & Answers about כשהוא היה קטן, הוא היה מספר לי על חלום יפה ואז היה מחייך.
כשהוא means when he.
It is made from:
- כש־ = when
- הוא = he
So:
- כשהוא היה קטן = when he was little
In Hebrew, short words like כש־ often attach directly to the next word.
Because it is doing two different jobs here.
In כשהוא היה קטן, היה simply means was:
- הוא היה קטן = he was little
In היה מספר and היה מחייך, the combination היה + present form expresses a habitual past:
- היה מספר = he used to tell / he would tell
- היה מחייך = he used to smile / he would smile
So the sentence is describing something repeated in the past, not just one single event.