It started off just like any other Tinder conversation: general chitchat over the course of a week that eventually got more flirtatious as the two people got to know each other.
Mark*, 38, from Sydney, had no idea that this playful conversation was about to take a very sinister turn.
"Looking back even now there was nothing that struck me as unusual about the account, nothing that would tip me off as to what was about to happen," he told news.com.au.
The woman's profile that Mark had matched with said she was within a kilometre radius of him, which he said attributed him to the belief that he was speaking to a genuine person.
After a week of talking over Tinder, the woman suggested they move their conversation over to WhatsApp. It was at this point that Mark started to think that something was off after she gave him an Indonesian phone number.
"When I questioned her about it she said she was travelling in Australia for a while and that kind of eased my concerns and made me think it wasn't too unusual."
The conversation escalated to the point where the woman sent a nude photo to Mark, asking for one in return. Despite it being out of character, he agreed and sent one back.
It was at this moment that his flirtatious conversation turned into a living nightmare.
The woman he was speaking to sent through a message demanding $500 or she would send the explicit picture of Mark to all of his friends and family.
To back up their threat, the scammer sent through screenshots of Mark's Instagram, Facebook page and the names of a number of his family and friends.
"My initial thinking was not to pay. They told me they only wanted a one-off payment and that they would make a video of them deleting all the photos afterwards," he said.
"You know it is a lie but you want so badly to believe them."
Mark is a marketing manager for a multinational company and he knew that if that picture got out his career would be affected, so in desperation he transferred the money.
"The money arrives and of course they tell me it's not enough," Mark said.
"They then start repeating all the same threats as before."
It was at this point that Mark started looking for help and came across Internet Removals, an organisation that helps people get their sensitive content off the internet.
Online content removalist, Brendon McAlpine, helped Mark get as many personal details offline as they could so the scammer couldn't obtain any more information about him.
"When it first happens you feel totally helpless but speaking to Brendon it gave me the feeling that there were steps I could take to fix the situation," Mark said.
"This is the second week since the threat was made and I have gone through that whole worst-case scenario process of what would happen if the photo got out."
As of yet no one Mark knows has received the picture, but with the threat still looming he was faced with the task of telling his boss.
"I told my boss so just in case they do manage to get that content into my workplace he is aware of it," he said.
"I could tell he felt sorry for me and told me he would be as supportive as he could if it did come out.
"But as much as he can try and be supportive it would definitely have an impact on my career. It's the type of thing you can't live down.
"You look back on it and think, 'How stupid could I possibly be?' but at the time you just don't realise."
McAlpine told news.com.au that the first thing to do if you find yourself in a situation like Mark's is to stop all communication right away and never pay them.
"In Mark's case he did pay them and what happened from there is what will always happen — they asked for more money," he said.
"Most of the time these people are just looking to make some easy cash so if all communication goes dead then they will usually move on to the next victim."
The next step is to take screenshots of the conversation and gather all the information you have about the person and report it to the police.
McAlpine said that even though the police generally can't do anything about it if the scammer is overseas, it is good to have it on record in case something else happens.
They then worked on shutting down all of Mark's social media pages and getting his business-related photos, like those on LinkedIn, offline. This means that the scammer can't harvest any extra information that they can use against you.