Brendan, who is now 25 and works as an electrician in Sydney, said the breakup was "pretty brutal" and having spent more than $10,000 on the European holiday and engagement ring combined, he decided to go on the adventure anyway — with the ring in his backpack.
"She knew nothing about my plan," he said. "But I didn't want to tell her I got her a trip and ring because she probably would've come back to me and I didn't want her to come back for that.
"So two days before the trip started, I told her about the trip — but not the ring."
Upon arriving in Santorini, Brendan became good friends with the group leader on his Topdeck tour that provides overseas and domestic group travel experiences for 18 to 39-year-olds.
The friendship he developed with the leader on the tour helped him through some of the harder times encountered on what he thought would be his engagement holiday.
"When the Topdeck leader asked why I was travelling alone, I told her what had happened," he explained. "We bonded over that … and I told her about the ring."
It was during that moment while watching the sunset in Santorini, Brendan says he did the unthinkable, and the decision cost him $5000.
"I wanted to get rid of the ring, so I asked the group leader if she'd stand on the edge (of the cliff) and get rid of it with me," he said,
"At that point, I threw it off the cliff. I got her to video it, and it's probably the best video I have."
Brendan said while the decision obviously cost him thousands, it's one he would never regret.
"It cost me a lot of money, but the moment I threw the ring (into the ocean), a whole lot of weight lifted off my shoulders," he explained.
"A lot of stuff changed inside me as well in that moment, and I know it sounds cliche, but I really found myself in Europe after that.
"Yes, I wasted a lot of money, but I would do it all over again."
Brendan says he has no regrets about throwing the $5000 ring off a cliff where he planned to propose.
Brendan, who posted the footage of him throwing the ring into the Aegean Sea on social media, said he received mixed responses from people who watched the moment online.
"All my mates said that what I did was ridiculous and a waste of money," he laughed.
"I copped a fair bit of abuse for it … and it was a hard decision to throw the ring. But after she got with another guy — who she is still with — I knew the ring would be worth nothing and that throwing it away would be a more powerful moment than just going to get the money back for it."
