Michael Stephen Hollander’s quest to marry the victim involved sending her 1000 messages in 10 days, which included videos of him performing sex acts, smoking methamphetamine and "unintelligible ramblings".
The 40-year-old appeared in the Dunedin District Court yesterday, where he was jailed for 11 months for his "sustained campaign".
Judge David Robinson said the impact on the victim had been significant.
She wrote in a statement that she was concerned her ex would track her down and continue to harass her.
"She worries about what you’re capable of," the judge said.
"Your contact left her feeling repulsed and she has fears for her safety."
Within days of their break-up in April, Hollander began his torrent of electronic communication.
The court heard the messages oscillated between him professing his love, nonsensical rants and sexually explicit videos and one was overtly threatening.
During that period, Hollander took his pursuit of the woman even further.
On at least two occasions he travelled to the victim’s home and sneaked inside.
Once, he hid in a bedroom and only left when he was confronted by his ex-partner and her friend; and later he crept through a lounge and was again heading for the victim’s bedroom when he was rumbled and told to leave.
When police became involved, Hollander came clean.
"In explanation, the defendant stated he had sent the messages and videos to try and get the victim to come back to him so they could get married," court documents said.
When he showed up at court on May 28 and heard his bail might be opposed, he did not stick around.
A warrant for Hollander’s arrest was issued but he managed to evade officers when they attempted to catch him later that day.
His luck, however, soon ran out.
Police surrounded his home the next day and Hollander’s escape bid this time was unsuccessful.
The court heard he had spent the past three months behind bars — a "short, sharp shock", counsel Caitlin Smith described it.
She argued Hollander should be sentenced to intensive supervision, to provide wraparound support for him in the community.
Judge Robinson, though, took a different approach.
He said Hollander’s unlawful entry into the victim’s home was undoubtedly "sinister" and the worst offending of its type.
"You were trying to exert your will, that she rekindle the relationship with you," he said.
The court heard Hollander had previous convictions for breaching community-based sentences.
"Your history also shows that you have a capacity to dish out significant violence in a relationship," the judge said.
Hollander was jailed and convicted of a breach of the Harmful Digital Communications Act, smoking meth, possessing meth utensils, being unlawfully on a property and failing to answer police bail.
