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When Taylor County Sheriff’s Department Detective Harlan Schwartz knocked on the door of Robert’s apartment early on the morning of September 20, 1999, Robert wasn’t concerned. He had a good job, he was back together with his childhood sweetheart, and his life seemed to be moving in exactly the right direction. He was confident that he hadn’t done anything that would get him into trouble with the law.

It may have been that confidence that led Robert to talk to Detective Schwartz on the spot, without consulting an attorney or even taking time to think the situation through or talk to a friend. Maybe not, though—by all accounts, Robert had always been open, friendly, and social. He might have made the same decision under any circumstances.

When the detective started asking about a girl he’d dated  months earlier, Robert thought he knew what was going on. A week or so earlier, his ex-girlfriend, J., had called him out of the blue. Back when he’d been dating J., her mother had loaned him some money, and she wanted it back. Robert hadn’t had the money on hand to pay her immediately, and he’d heard her raise her voice in anger in the background as he talked to J.

Now, a police detective was in his apartment, asking questions about his long-past relationship with her daughter.

Robert wasn’t shy about admitting to the sexual relationship. In fact, he says now that he embellished a bit. Like many teens and young adults, Robert didn’t fully understand the law regarding age of consent in his home state. J. had been 15 when they were together, but he’d only been 17—a minor himself. He was sure that meant that their sexual relationship had been 100% legal. He may have been gloating a bit while he was hanging himself, thinking that J.’s mother would be in for a surprise when she realized that he’d been underage the whole time.

Whatever he expected to come from that conversation, it wasn’t a felony sex crime conviction that would ultimately send him to prison for four years of an eight-year sentence, haunt him for years to come, and require him to register as a sex offender.  Even if he had known enough to expect criminal charges, he could never have imagined that in his mid-thirties, as a successful business man with a family, he would still be struggling to manage the fallout from that brief relationship.

Perhaps the saddest and most ironic thing about Robert’s story is that he had a rough childhood and adolescence. He wasn’t always a good kid. By the time he was fourteen, he’d had several encounters with local law enforcement.

At 12, he was with a friend who stole a carton of cigarettes. At 14, he forged a signature on a check a friend had stolen from his mother and accepted some of the money after his friend cashed the check. Over the next couple of years, he racked up an underage drinking charge, what he describes as “a lot of curfew violations,” and a theft charge relating to an inexpensive necklace. At 15 or 16, he was caught joyriding with his cousin, who is now serving a 12-year prison sentence for robbing a gun shop.

But, when he met J. in the fall of 1998, that was all behind him. He was 17, working steadily, and just months from renting his first apartment. He hadn’t had a brush with the law in a couple of years, and he had started to forge his own path. On that day, he was just a typical teenaged boy, hanging out with friends when a pretty girl drove up with a friend and caught his attention. If anything set him apart at that point, it was that he was a bit more self-sufficient than most kids his age. He’d started working at 15, taking on short-term jobs at two fast food restaurants before moving into roofing and drywall work.

Robert says that he initially thought J. was 16–just one year younger than he was–because she’d driven up to the house. Under Wisconsin law, what happened next would have been a crime regardless, though a less serious one.

What followed is a familiar story for most of us, one that plays out among teenagers all over the country every single day. J. gave Robert her phone number, and a few days later, he called her. They dated, met each other’s friends, and got to know each other’s families. Like many romantic relationships among teenagers, though, this one didn’t last long.

While J. was still in school and living with her parents, Robert was working full time in construction. In the spring of 1999, he had an opportunity to work in the Elkhorn area, more than three hours from the town where J. lived and went to school. Unsurprisingly, the relatively new relationship couldn’t weather the separation. The two parted ways near the end of the school year, just six or seven months after they’d met.

It was the kind of relationship that both Robert and J. might both have relegated to a vague memory if just one small thing had gone differently: if J.’s mother hadn’t loaned Robert money, if he’d had the money to give her on the day J. called, if she’d filed a small claims suit instead of calling the police, if he’d politely declined to talk to the detective who knocked on his door. If any one of those things had played out differently, both Robert and J. would likely have carried on with their lives and rarely, if ever, looked back.

But, Robert did owe J.’s mother money. He didn’t have it to give her when she called. She called the police. Robert answered their questions when they arrived. And, their short-lived teenage relationship took center stage in both of their lives. Robert is still living with the fallout 20 years after their break-up.

Update: Since publication of this piece, Wisconsin law has changed, as described here.