"It won't give me much pleasure to send you to jail," he said.
But the judge warned Dry that he'd better to cooperate with his probation officer and agree to any help he might need.
Through his lawyer Nicole Johnston, Dry pleaded guilty to five theft charges.
A police summary of facts says his first target was a jewellery store at a Christchurch shopping mall on September 12 last year.
He asked staff about buying a $5000 signet ring and was allowed to try it on.
But with the ring on his finger, he ran from the store, and out of the mall.
Other subsequent raids saw Dry and his co-conspirator ask about particular jewellery items at various stores in Christchurch and Wellington – and when they were shown to them, the pair would swipe them and run off.
The stolen jewellery amounted to tens of thousands.
When police officers caught up with Dry, he claimed he'd been pressured into the thefts after being "threatened by an unknown male", the police summary of facts says.
Dry also claimed he couldn't remember ever being at other stores.
He will be sentenced in August.