Conrad Roy, who committed suicide after receiving texts from friend Michelle Carter, shares pain of learning new details about teens' relationship

Aunt of Teen Who Killed Himself After Friend Allegedly Encouraged Him Shares Heartbreak: 'There's a Hole in Our Family'

It has been more than a year since Lynn Roy’s 18-year-old son killed himself, but the pain has not eased as new details continue to emerge in Massachusetts court hearings.

“It has been a very difficult year. I don’t think there has been any healing,” Roy’s sister-in-law Becki Maki tells PEOPLE. “In fact, over the last few weeks, it has gotten worse.”

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Conrad Roy III died from carbon monoxide poisoning generated by a gas-powered water pump he ran inside his car in a Fairhaven, Mass., parking lot in 2014. Police discovered he had a texting relationship with Michelle Carter, now 18, who they say encouraged Roy to go through with it.

“There are a lot of unanswered questions as the details are released. It’s very difficult to grieve and to move on the wounds, you would think would be healing, but they’re just getting deeper,” Maki, 38, says. “The details are so painful. It’s heartbreaking.”

According to documents obtained by PEOPLE, Carter, who faces 20 years in prison, sent messages to Roy saying, “You just have to do it,” “Tonight is the night,” and “It’s painless and quick.”

When Roy hesitated about killing himself, Carter allegedly texted, “You always say you’re gonna do it, but you never do. I just want to make sure tonight is the real thing.”

Carter has been charged with involuntary manslaughter. She has pleaded not guilty. Last week, her attorney filed a motion to dismiss the case based on the lack of evidence. In response, the prosecution released texts, which were seen for the first time.

Carter allegedly said his parents would be able to “move on” from Roy’s suicide, but Maki says they never will.

“There’s a huge hole in our family,” Maki says. “He cared so much about his family. He had a lot of friends. He was an all-American kid that his family was very proud of.”

For now, Maki will continue to attend court hearings. The next one is Oct. 2 when the judge is expected to decide whether there is enough evidence to move forward with the case. Maki says the defense’s argument that Carter’s texts are protected by the First Amendment is far-reaching.

“I think he’s grasping at straws,” Maki says. “She was inciting him to cause harm to himself [and] taking advantage of someone that she knew was depressed and vulnerable.”