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Shawn Lerner and Laura Babcock are together at a February, 2011, birthday party for Ms. Babcock. Dellen Millard, right, who stands accused of murder in relation to Ms. Babcock’s disappearance, was also there that night.

There was no time to grab a coffee when Shawn Lerner arrived a few minutes late at a Starbucks west of Toronto on a warm afternoon in late July, 2012.

He was there for a meeting. His ex-girlfriend had been missing for nearly a month and he had a lot of questions.

Sitting across from him with a magazine and an icy drink was a rushed Dellen Millard – the man Laura Babcock had called eight times before she mysteriously disappeared and who would later stand accused of her murder. Their brief discussion left Mr. Lerner feeling deeply uneasy.

"First, he denies all the calls: 'Maybe we spoke once or twice, but definitely not eight times.' Flat-out denies it," Mr. Lerner recalled. "Then I showed him the phone bill and his tone totally changed: 'Okay, yeah, we spoke. She was looking for drugs and for a place to stay,' and he denied her on both of those requests. And then he just had to go. He was in a rush – had to go."

Mr. Lerner didn't know it at the time, but Ms. Babcock, a bubbly 23-year-old, had allegedly been dead for more than three weeks.

After the meeting, Mr. Lerner contacted Toronto Police, but says he lacked confidence in their investigation and was conducting his own search. Today, after two additional deaths for which Mr. Millard stands accused, Mr. Lerner is haunted by the heavy weight of hindsight. What if he had pushed harder for the police to find out what had happened to Ms. Babcock? Would Tim Bosma and Wayne Millard, still be alive today?

"What really kills me in all of this is that … by the time we suspected she was missing, it was already too late. But I always think that if I did more and if the cops had actually taken this seriously, maybe Tim Bosma would …" Mr. Lerner said, his voice trailing off. "I mean who knows. I always play 'What if?' but that's a really cruel thing."

Little happened with Ms. Babcock's case until the charred remains of Mr. Bosma, 32, were found on Mr. Millard's farm south of Kitchener, Ont., after the heating and air conditioning technician took two men to test-drive his pickup truck in May, 2013.

In the aftermath of Mr. Bosma's killing, Toronto Police reinvestigated Ms. Babcock's disappearance along with the death of Mr. Millard's father, Wayne, in November, 2012.

Then last month, Mr. Millard, 28, and his friend Mark Smich, 26, were charged with first-degree murder in relation to Ms. Babcock's death. Mr. Millard, an heir to his family's aviation business, faces an additional count of first-degree murder for his father's death, which was initially deemed a suicide. Both men also face the same charge in relation to Mr. Bosma.

Mr. Millard and Mr. Smich have maintained their innocence. Mr. Millard is "quite upset" about the fresh murder charges, said his lawyer, Deepak Paradkar. "But on the other hand, he's pretty determined to fight them," he said.

Back in late June, 2012, Ms. Babcock's friends and family began to worry after losing touch with the University of Toronto English and drama graduate. Mr. Lerner, who had remained a close friend after they broke up early that year, filed a missing person's report and began distributing flyers and interviewing her friends.

In the process, Mr. Lerner found out that Ms. Babcock, who struggled with mental-health issues, had been using drugs and working as an escort while bouncing between friends' couches after moving out of her parents' house because of a disagreement. He also learned that she had begun a sexual relationship with Mr. Millard, a long-time friend, at some point in the first half of the year.

As he grew increasingly concerned, Ms. Babcock's cellphone bill arrived in her parents' mailbox in late July. Mr. Lerner, a 24-year-old small business owner, called each number, even tracking down some of her johns in person to see if they had any information. He also sent a text message to Mr. Millard, who he had met a couple of times, mentioning that Ms. Babcock's last eight outgoing phone calls – lasting just a minute or two on July 2 and 3 – were to him.

Mr. Millard sent a brief reply, obtained by The Globe and Mail: "Heard about that, don't know where she is."

After Mr. Lerner sent three more texts pleading for information, Mr. Millard replied: "Doesn't sum up into a text message, shall we grab a coffee later today or tomorrow?"

Mr. Millard was waiting on the patio when Mr. Lerner arrived at the Starbucks in a Chapters across from Square One mall in Mississauga on July 27, 2012. He was clearly in a hurry; there was no time to engage in small talk or for Mr. Lerner to get a coffee.

Throughout their conversation, which lasted less than five minutes, Mr. Millard was "calm" and "pretty collected" and even "cocky" as he acknowledged speaking by phone with Ms. Babcock, Mr. Lerner recalled.

"I certainly thought it was fishy, the fact that they had all these calls, the fact that he denied all these calls at first," he said. "I thought that, at the very least, warranted further interest from the police."

Mr. Lerner is considering filing an official complaint about the initial Toronto Police investigation into his friend's disappearance. Along with some of her relatives, he faults police for doing little, including not following up on her phone records. Mr. Millard was not questioned at the time, according to Mr. Paradkar.

Toronto Police spokesman Mark Pugash declined to comment, saying: "Any of the questions concerning the efforts that were made will emerge during the course of the court case."

Ms. Babcock's parents, who are clinging to a belief that she may still be alive in the face of police unwillingness to say whether her body has been found, also would not discuss the investigation.

"I'm not going to make any comment on that, okay?" said her mother, Linda. "I'm still hopeful."

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