How weird would it be to be some kind of leader of a military resistance and have to go and pick out some dude to go back in time to sex up your mom?
According to the videogame "Terminator: Dawn of Fate" That isnt Jo'connors intention...reese and John are to travel to Skynet @ Nourad to stop the time machine from sending the terminator back to prevent Jo'connor from being born - the fact that reese goes thru time is a last minute resort and not the plan.
It isnt pre-meditated MILF pimping on J O'connors behalf.
But it's already known in T1 that Connor gave Reese the picture of his mom with the intent to get her sexed up. Or at least, heavily implied IMO.
He's just lucky Reese didn't go anal.