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At 16, Joran van der Sloot, a star athlete at the International School of Aruba, was smitten with local girl Melody Granadillo. He wrote her love notes, took her to concerts, danced with her in the rain. When her 17th birthday rolled around, he gave her a vase filled with her favorite candy-red Skittles-then paid homage to his "dream girl" in a school essay. "Love is the most important emotion," he wrote. "Love can be something small that you will remember forever like holding hands or red skittles [sic]." After van der Sloot (cyberhandle: loverboy362) e-mailed her the essay, Granadillo pasted a copy into the blue diary that they kept together and filled with poems, essays and e-mails. But Granadillo had a problem: According to her, Joran was a lothario. Seven months on, she claims, his cheating broke them up. "He has a problem with lying," says Granadillo, who says she remained friends with van der Sloot. "But in general, he is good at heart."

It is clear now that van der Sloot, 22, is far more sinister than that. On June 7 he confessed to murdering Peruvian college student Stephany Flores Ramirez, 21, who was found bloodied, with her neck broken, in a Lima hotel five days earlier. And that murder occurred, chillingly, on May 30, five years to the day after American high school graduate Natalee Holloway, 18, disappeared in Aruba during a graduation trip-after last being seen with van der Sloot. Though he was arrested twice, van der Sloot was never charged with a crime in the case, and Natalee's body has yet to be found. Still, Natalee's family hope shocking new developments will bring some closure to their unresolved grief. "I have some resolution knowing that he's going to be spending possibly the rest of his life in a Peruvian prison," says Dave Holloway, Natalee's dad.

Even before the confession, Peruvian authorities possessed a trove of potentially damning video evidence: van der Sloot and Flores playing poker at the same table at the Atlantic City Casino in Miraflores; van der Sloot and Flores entering room 309 of Hotel Tac together; van der Sloot leaving the room alone more than three hours later-toting a suitcase and backpack-before fleeing by taxi across the border to Chile.

Four days after he was arrested on June 3 in Chile and flown to Peru, van der Sloot told authorities he grabbed Flores by her neck when she began reading articles about him on his laptop. "I didn't want to do it," he said. "The girl intruded in my life." While it's unclear how the murder investigation in Peru will impact the Holloway investigation (see box), Aruban officials hope to look at evidence in the Flores case. "I keep thinking, 'Finally there's going to be some justice served,'" says Dave Holloway.

How did van der Sloot come to be connected to two young women who met horrible ends on two different continents five years apart? Friends and acquaintances who have known him over the years tell PEOPLE that since Natalee's disappearance, van der Sloot has led a peripatetic, playboy existence that took him from Aruba to Holland to Thailand-a life heavy on money problems, gambling and marijuana consumption, but short on support from friends and family. Even his mother, Anita, who vigorously defended van der Sloot after Holloway's disappearance, this time told PEOPLE only, "I haven't been in contact with Joran for a long time, not since his dad died" in February.

Some who know him claim his most recent downfall follows years of ostracism after he was implicated in the Holloway case. "All his friends turned their backs on him," says Aline Hibbert, 22, another former girlfriend from Aruba. "I've seen him cry because people have left him behind." She recalls a shopping expedition with him in Oranjestad, the capital of Aruba, where people shouted, "Go back to Holland!" "He just said the people are being unjust," she says. "He didn't even talk bad about anybody."

Others say, however, that before van der Sloot acquired what one of his former lawyers, New York attorney Joe Tacopina, calls a "bull's-eye on his back," van der Sloot already showed signs of trouble. The son of a prominent lawyer, he was known to lose his temper on the tennis court, sometimes tossing his racket dangerously close to spectators. "He was arrogant, always," says one tennis mom. "He had anger issues." A fellow tennis player adds, "He was always a bully, but he got so many girls. A real womanizer."

Hibbert's memories of van der Sloot are different. She recalls the star-shaped belly rings he gave her to commemorate their watching shooting stars together, his gentlemanly manners and goofy sense of humor. "He is not how everybody is painting him," she says. The weight of recent years, she says, has made him "more serious" and destroyed the "magical kid" she used to know. Granadillo similarly says he's lost "that inner glow."

What van der Sloot has had, up until his capture in Chile, is an increasingly desperate time making a life for himself as he's shifted between continents, trying to get a fresh start. After his first arrest in June 2005 for the Holloway disappearance, van der Sloot, an honors graduate of the International School of Aruba, abandoned plans to study sports psychology in Florida and returned to Holland, where he enrolled at the Hogeschool Arnhem/Nijmegen to study international business management. "On the first day he explained to his class who he was and what he had gone through," says Gert de Groot, the college's director of international business and communication. Over the next two years, van der Sloot's class attendance dropped and his grades plummeted until he flunked out.

After his second Aruba arrest and release in late 2007, he took off for Thailand. In June 2008 he enrolled at Rangsit University International College, which has an exchange program with a Dutch university. The hostility from the Dutch community there was palpable. "He had a hard time studying here," says an American friend and fellow student. "A lot of people didn't want to be associated with him."

During this period his gambling continued. One Aruban acquaintance, Sjona Vrolijk, recalls him chatting up a woman in a casino. When they started to leave together, Vrolijk stopped the woman and said, "Do you know who he is?" Then she mentioned the Holloway disappearance. "He called me a dumb bitch and told me to get away from them," she says. "He was scary."

In Thailand he rode a motorcycle and moved into a $1,000-a-month, three-bedroom house that he eventually shared with his girlfriend from California. "They seemed pretty happy together," says a Thai acquaintance. On weekends he frequented beaches by day and a popular bar strip by night. After a year his landlady evicted him, tired, she says, of the noise and damage that resulted from his many parties. "He was smoking and drinking with girls," she says. "He pretended to be a nice guy, but he's not." She says that after she went to the Dutch embassy and complained about the damage to her floors and tiles, an uncle of van der Sloot's covered the $2,000 in damages. No longer with his girlfriend, he moved into a shabby $150 studio apartment.

In May 2009 he was expelled from Rangsit with a grade-point average of 1.31 out of a possible 4. By then, says attorney Tacopina, van der Sloot "was a gambling addict," and, as a result, "his parents stopped supporting him." A few months later, van der Sloot somehow found funds to open a coffee shop. He put in a lovely but impractical wood floor and glass panels that featured cascading water. Soon he was out of funds. Many students refused to patronize the shop. And he often failed to stock such basics as bread and cheese. With the shop open only intermittently, he eventually had to lay off his Thai staff.

That August, desperate for money, he offered an interview to Jaap Amesz, a Dutch reality-show star, for pay. "I gave him money to solve his debts and the rent for his apartment," says Amesz. In exchange van der Sloot offered a new version of events in the Holloway case: He said she took cocaine and fell off a balcony, after which he dumped her body in a swamp. "His moods can switch from one second to the other," says Amesz. "He has a huge gambling, smoking and drinking addiction." To that list, Tacopina adds marijuana.

By February van der Sloot was so broke that he was living in his restaurant. Following the Feb. 10 death of his father from a heart attack, he negotiated the sale of his restaurant for $12,000 to an American man and Thai woman. The woman says he was distraught over his father's death, sobbing and screaming and claiming he needed money for a plane ticket home. "We made the contract that if he came back, he could buy the cafe back," she says.

Van der Sloot won't be returning anytime soon. Murder in Peru carries a maximum sentence of 35 years in prison. He was also hit last week with extortion and wire fraud charges in the U.S. for allegedly trying to extort $250,000 from Natalee's mother, Beth Holloway, to reveal the circumstances of her daughter's death and the location of her remains. "The fact that he would try to extort money from my sister on the terrible deeds he's done is just despicable," says Beth's brother Paul Reynolds. Those charges could land him in a federal prison. The Holloway family hopes Flores' murder may jar loose new information in Aruba. But if not, says Natalee's dad, Dave, "in my mind, he'll be thinking about Natalee's case while he's sitting behind those prison bars."

  • Contributors:
  • Siobhan Morrissey/Aruba,
  • Brechje de Koning/Holland,
  • Karen Emmons/Thailand,
  • Pamela Montes Iturrizaga/Lima,
  • Elizabeth McNeil/New York City,
  • Jeff Truesdell/St. Louis.