Bevan Lee Stoneman's ex-partner was at the beach with her children on Christmas Eve when she realised he had followed her and was watching them from his car.
Stoneman breached a protection order five times in the past and was convicted of three more on Tuesday, earning him six weeks in jail. He appeared in the Whanganui District Court and admitted the charges.
The protection order was granted in favour of the ex-partner and her two children in 2009.
Of the latest breaches, the first happened on December 21 when Stoneman spoke to the victim's 7-year-old daughter unsupervised and gave her money, Judge David Cameron said.
The other two breaches happened when Stoneman drove past the victim's sister's address on December 24 and saw the victim packing the car to go to the beach.