My mistake, I thought that God’s curse was also on the women, but apparently it was only the men who were cursed to die in the desert, so Caleb would have been able to marry whomever and whenever he wanted.Not too clear on this , but it seems that Caleb and Joshua entered the promise land unmarried. If either of them got married after they entered the promise land, then they would have had to have married someone from the next generation since the previous generation died in the desert except for Caleb and Joshua. I know that Caleb was married at some point.
Caleb was about 80 when he entered the promised land. Joshua’s age when he entered the promise land ranges from about 60 to around 80 depending on who you believe. The Midrash has Joshua taking over from Moses at 82 and then marrying Rahab when she was in her 50"s.After 40 years of wandering the desert, how were Joshua and Caleb able to fight the inhabitants of the promised land? God must have given them a second wind/spring as a result of their obedience to Him.