He was at the centre of a sex scandal, then was expelled from the National University of Singapore (NUS).
Later, he was arrested and held without bail in Malaysia for making racially inflammatory remarks.
But notorious Alvin Tan remains defiant.
I have no regrets, he told The New Paper.
Indeed, he thinks his life can't get any better.
"I enjoy being the subject of gossip, lah," Tan, a Malaysian, said in a phone interview from Kuala Lumpur.
As half of infamous couple Alvivi, he was recently in the news again after his split from partner Vivian Lee.
The former NUS scholar first earned public infamy from his sexual exploits on a blog called Sumptuous Erotica, which went viral two years ago.
As a result, Tan, who turned 25 last month, was expelled from NUS Law School and stripped of his scholarship in November 2012.
Last January, the duo had their own sex-themed talk show. In July, they were arrested for making a racially-insensitive remark on Facebook.
Despite calling himself a "magnet for legal problems", Tan is not planning to lie low.
The self-proclaimed aspiring porn star claimed that he was organising sex parties just before the couple were arrested. They were denied bail and spent eight days in jail.
This experience inspired a few chapters of his new book, Sex, Pork and Persecution.
Is the breakup another publicity stunt?
Tan told The New Paper that the breakup is "possibly permanent" and everything they posted online was "real".
The pair got into an online squabble, each flinging accusations of betrayal earlier this month.
CLOSE FRIEND WITH BENEFITS
"Some things are hard to define, but I would consider Vivian as a super close friend with benefits.
"I'm uncomfortable with the label of girlfriend, because this means it is long-term and possibly leading to marriage.
"I could never see that with her, or any girl," he said.
The couple were cohabiting at Tan's apartment and a friend's place after Lee was thrown out of her home in Johor in 2012. But Lee eventually moved out because they both needed some personal space.
Tan claimed that he caught Lee having sex with their friend in her own apartment on Dec 28.
"I confronted them, of course.
"What did you expect me to do? Say 'oops, I'm sorry' and close the door? This is not cool... not honest."
Is the latest twist a way to create buzz for his new book? After all, he has so far failed to find a publisher for his tell-all.
"I'm hoping to publish my book in a few months, but there are many hurdles. It's a sensitive topic, publishers are worried, there is government censorship...
"I'm going to deal with it when it comes," he said.
The couple were charged under the Sedition Act, the Film Censorship Act and the Penal Code and face up to RM50,000 (S$19,000) in fines, five years' jail, or both, if convicted.
The trial, which was to have begun on Tuesday, has been postponed to Feb 28.
The couple's lawyer fees have cost RM80,000 so far, which Tan, who runs a software business, paid from his savings.
I'm hoping to publish my book in a few months, but there are many hurdles. It's a sensitive topic.