They had been in contact for months when the woman who identified herself as model "Bree Condon" made the first request for money.
Marc Puleo said the pair met online and exchanged telephone calls and e-mails. "Bree," he said, sent him pictures of herself. Though they never met in person, Puleo said that when "Bree" told him she was having financial difficulties, he stepped up to help.
According to an affidavit filed with the Municipal Court of Travis County in Austin, Texas, Puleo sent more than $10,000 to a "Bree Condon" he met on the social networking site SeekingMillionaire.com in January 2008.
Puleo, who did not immediately respond to requests for comment from ABCNews.com, said in the affidavit that during the time the two were in touch, he truly believed the person he was talking to was Bree Condon, a 23-year-old model from Newport Beach, Calif.
But earlier this month, a 24-year-old man, Justin A. Brown, was indicted by a grand jury of felony theft in Austin, Texas, for allegedly impersonating the real Bree Condon, a Guess jeans model, online.
Investigators believe Brown spent several years swindling wealthy men online through Facebook, MySpace, SeekingMillionaire.com and other Web-based social networks, using fake accounts to allegedly trick the men into giving him money and other gifts.
Brown was ultimately charged with theft of $1,500 to $20,000, but authorities estimate the total could be much more. And though they say this case is unique, they also say that online scams are a serious problem.
"A lot of victims don't want to come forward at this point," said Det. Carl Satterlee, the Austin detective assigned to the case. He said some men are embarrassed to admit that they fell for an online scam -- and one allegedly perpetrated by a man, no less.
Condon's agent did not immediately respond to requests for comment from ABCNews.com, but in a statement to the Los Angeles Times, a private investigator hired by the model said she was working with authorities.
Condon "pursued this with law enforcement because she was very concerned about other people being conned by this impersonator, especially since he was apparently taking money from people and engaging in behavior that Bree would never participate in," the investigator, Jon Perkins, told the Times.
Brown was indicted Jan. 7 and is currently in jail in Austin. His court-appointed attorney did not immediately respond to requests for comment from ABCNews.com.
Satterlee alleges that Brown was able to stay under the radar for so long because he used his own talents and the Internet to his advantage.
"He was convincing because has such a feminine voice. He was also very smart," Satterlee said. "He was able to get a lot of personal information about Bree and obtain personal photos of her that helped convince these guys who he said he was."
But ultimately, authorities say Brown wasn't smart enough to evade detection forever. One evening last fall, he reportedly sent the message that did him in.
John Carbona, a Fort Myers, Fla., private investor, said that Brown reached out to him through a location-based social network called Who's Here.
Posing as "Bree," he allegedly told Carbona that a friend of his gave her his number and, though she was an emerging actress and model, was in a tight financial spot.
While traveling between Los Angeles and Texas, "Bree" said she lost her luggage, including her wallet, and was "desperate for money," Carbona said.
But Carbona, whose father and grandfather were police officers, said it was a tough tale to swallow.
"I said, 'let me get back to you,' and I did some checking around," he said.
Ultimately, he tracked down the real Bree Condon in Wales, and she informed him that an impersonator had been causing problems for years and referred Carbona to her private investigator, Perkins.
Carbona said he told Perkins that he "was raised in a family of very skeptical, investigative minds and I'd like to plan a sting."
Using the GPS-enabled social network Who's Here, Carbona said he figured out that "Fake Bree" was in Austin. "From that point on it became just a cat and mouse game," he said.
After a few months of phone calls, Carbona said he was able to convince "Bree" to let him pay her motel bill. When the credit card authorization form arrived by fax, Carbona told Condon's private investigator about Brown's location. Perkins then notified Austin authorities, who apprehended Brown in his hotel room.
"The technology was really the key to it, to determine his distance from me," Carbona said. "And enough experience with hotels to know that you can pay remotely."
Carbona said he couldn't believe that "Bree" was really a man. Even after he knew the suspect, Brown, was trying to con him, he said he couldn't detect it in his voice.
"I listened so intensely to try and pick up any sort of slip. He stayed in character perfectly. He was really talented in what he did," Carbona said. "He just played the woman perfectly."
And though some may wonder how wealthy, accomplished men fell for Brown's alleged trick, Carbona said he was "very convincing at being this damsel in distress."
"It's pretty sad for a lot of people who thought they were helping someone who was in need," he said. "We're living in a time where the economy has turned a lot of normal livelihoods into abnormal livelihoods."
Those familiar with online social networks say scams like Brown's happen more frequently than you might think.
Stephan Smith, a spokesman for SeekingMillionaire.com, said that members call with reports of blackmail and extortion reports "all too often." While large-scale scams involving thousands of dollars are rare, the site removes fraudulent profiles on a daily basis, according to Smith.
"Where you bring together wealthy individuals and those who seek their companionship, you have a lot of potential for fraud," he said.
Members are flagged if they spam others with messages or if the gender indicated in their billing information doesn't match the gender provided in their profile.
He said the site actively cautions members against sending money before they meet someone in person. "That's a warning that every member sees every time they log in," Smith said.
But despite the warnings, some members still find themselves at the mercy of con artists.
"A lot of this dating is based in fantasy," he said. "Unfortunately, that excitement can kind of prevent the normal precautions one might take in real-life settings."
One member of SeekingMillionaire.com, who asked that his name be withheld, said he was in contact with the fake "Bree" in October 2008.
He said the two spoke over the phone over the course of a few nights. But when she asked him for $500 to buy a Halloween costume, his defenses sprang up.
"I specifically said to this person on the phone, 'this is the kind of thing people do when they're getting scammed,'" he said, adding that communication petered out after that.
He never imagined that "Bree" was really a man, but now that he knows the truth, he said he's not surprised.
"I've always been a little skeptical," he said. "If it's too good to be true, it probably is. Hot women don't just fall off trees."