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Connecting Online Leads One Woman to a Con Artist

Protect your heart and finances from a romance scam

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Adapted from Scam Me If You Can (Portfolio–Random House/AARP) by Frank Abagnale

Melissa Trent's heart jumped when she saw a new message from a user called “lovetohike1972” on her account with dating website Plenty of Fish that Thursday in April 2017. A 40-something single mom, Melissa had experienced bad luck finding anyone nice who shared her love of the outdoors, so she was eager to check this person out. She was not disappointed. His account featured photos showing a handsome, fit, smiling guy in hiking clothes, engaged in outdoor activities. His interests included hiking, biking, skiing and craft beer — all things that Melissa liked.

After exchanging a few messages, she gave the man her cell number. He reached out that evening. His name was Jeff Cantwell. New in town, he had just relocated to Colorado Springs from Alaska.

A few days later, Melissa agreed to meet Jeff. He looked just like his photographs; that gave her a feeling of security. He regaled her with stories about his adventures. There was no argument over the bill; Jeff paid. A few days later, he asked what her two daughters liked to eat and then came over to make spaghetti and meatballs.

The two were soon in constant contact. Jeff told Melissa he'd lost his parents in a car accident that had also claimed the life of his fiancée and their baby. He said he'd been in Afghanistan, where he was injured.

"We really liked each other,” she says. Or so it seemed. But soon Jeff's behavior started to raise red flags.

Jeff asked to borrow a little cash. He was having issues with his Veterans Affairs benefits. Whenever a check was deposited, his account froze until the check cleared. It seemed plausible to Melissa. And Jeff said he needed only $100, to see him through the weekend, and he would pay it back promptly on Monday. Then they decided to go to a casino, and Jeff asked if she could instead withdraw $200 from her account — $100 to get him through the weekend and $100 more for them to gamble with. She consented, and they stretched the gambling money for 10 hours of fun before it was gone.

During their time at the casino, she overheard Jeff talking to another customer about living in Alaska and heard him say, “My mom is Inuit,” in the present tense. But he'd told Melissa that his parents were deceased.

The following Monday, Jeff said he was still having trouble with his account and needed to drive to a branch of his bank an hour away. Despite misgivings, she agreed to let him take her new Audi. And she reluctantly let him borrow a credit card for gas.

When hours passed without word from Jeff, Melissa texted him. He said that by the time he had gotten to the bank, it was closed. He'd stay overnight, sleeping in her car, in the bank parking lot. “Chill out,” he texted. He'd never spoken to her like that.

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Have you seen this scam?

  • Call the AARP Fraud Watch Network Helpline at 877-908-3360 or report it with the AARP Scam Tracking Map.  
  • Get Watchdog Alerts for tips on avoiding such scams.

Melissa was finally forced to face the likelihood that something was very wrong in her new relationship. When Jeff refused to prove he was really at the bank, she decided to call the county sheriff's office.

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Police soon informed Melissa that “Jeff Cantwell” was actually Jeffrey Dean Caldwell, a 44-year-old criminal who had been incarcerated in several states for felonies ranging from burglary to writing bad checks.

Caldwell often trolled internet dating sites and trailheads looking for targets. He'd been paroled in September 2016, after serving time for identity theft in Colorado. But after he connected with Melissa, he had stopped checking in with his parole officer.

Eventually, Caldwell was arrested, in South Dakota. By then he'd maxed out Melissa's credit card and cleaned out her bank account.

Melissa got her Audi back, but it was a mess. Caldwell had gone on a craft beer tour and decorated the car's exterior with stickers from breweries he had visited.

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Lessons Learned

Since the first internet dating sites appeared, in 1993, online dating has soared — and so have romance scams. In Melissa's case, the two people actually met. More commonly, the fraud is done entirely online by an impostor, often working several romance scams at once, often from a foreign country (many of these scams come out of Africa). These swindles often target older Americans, who might have more financial resources and a greater chance of being alone. To avoid being the victim of a romance scam:

  • Go outside the dating site to research the person. For example, use the website TinEye or Google Images to “search by image” and see if that person's photo shows up in other places under a different name.
  • Be skeptical of stories designed to elicit sympathy, like Jeff's account of his family being killed in a car crash and his claim that he had been injured in Afghanistan.
  • Beware of requests for money — the biggest red flag. If that happens, say no and go on full alert.
  • Never provide your last name, phone number, address or place of work until you've gotten to know someone well enough to trust him or her.
  • Turn off location settings if you use a mobile app for dating, so cons can't figure out where you live or visit.

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spinner image cartoon of a woman holding a megaphone

Have you seen this scam?

  • Call the AARP Fraud Watch Network Helpline at 877-908-3360 or report it with the AARP Scam Tracking Map.  
  • Get Watchdog Alerts for tips on avoiding such scams.