Justin Massler set up a fan blog about the businesswoman and in a disturbing post earlier this year (Feb10), revealed he had attempted to telepathically connect with her.
Massler was subsequently detained by cops in Reno, Nevada after an arrest warrant was issued in New York, where Trump lives.
The man appeared at Manhattan Criminal Court on Thursday (01Apr10) and was charged with six crimes, including stalking in the third degree.
He was subsequently released on $16,000 (£10,000) bail, and ordered to stay away from the daughter of TV tycoon Donald Trump.
But after just three days out of prison, Massler allegedly sent a bizarre email to popular American writer Tucker Max, urging the bestselling author to "talk him up" to Trump.
In the message, sent on Sunday (04Apr10) and obtained by the New York Daily News, Massler allegedly wrote, "Obviously right now, she is probably not that into me since she filed the stalking charges and I'm in the doghouse with her, but later on I'm going to try and recover and then actually win her over.
"Talk me up, perhaps saying, 'Oh yeah, he's a cool guy who just has insanity problems at times, but if he recovered from insanity, he would be cool.'
"I would be the first deranged stalker to later end up (with) the exact chick who originally sought to have him put in jail."
Meanwhile, Massler's mum Randee has apologised to the Trumps for any distress her troubled son has caused: "He wrote nasty things and crossed the line. I can feel for Ivanka Trump and her family. If he caused her to be afraid, I'm very sorry for that."