I Kissed Dating Goodbye worked for Ly, and it worked for many others. It worked too for author Joshua Harris, who married at 23 and wrote a follow-up book about his courtship with his wife. But that’s not the story of many other readers who followed the book’s ideas and now, years later, voice disappointment and regret. Some have called the book “legalism at its finest” and claim it “ruined lives.” Some say it engendered a culture of judgmentalism, pressured inexperienced people into marrying the first person they dated, and caused them to fear intimacy of any kind with the opposite sex.

Back when the book topped the bestseller list, many of its readers were in their teenage years—a stage typically marked by raging hormones and dating experiments, when peers were trembling over their first kiss and parading their first official boyfriend or girlfriend in school. Kids broke love vows, lost their virginity, broke hearts. Those who adhered to the no-dating rules of the courtship movement avoided those messy experiences for something they hoped would be bigger and better.

Now most of these individuals are in their 30s—a different season in life, when they’re paying their own bills. Some say they’re ready for marriage, yet have been unable to find a mate through the means of courtship. Others have married yet now have negative feelings about the impact of I Kissed Dating Goodbye. If you ask young Christians to explain how the book shaped their views on dating and marriage—as I did for this story—some will tout the benefits. But many others will claim it did them more harm than good.

DONNA ROSS’ COPY of I Kissed Dating Goodbye is dog-eared and marked with highlights and annotations. As a homeschooled teenager in Florida, Ross attended Harris’ book tours, bought the cassette tapes of his speeches, even tacked a poster of his face up on her bedroom wall (“What, he was cute!”). She bought extra copies of I Kissed Dating Goodbye and passed them out to her friends: “I wanted everyone to see this vision of a beautiful community, of heaven. I thought if everyone was doing this same thing, no one would get their hearts broken.”

Ross’ parents were divorced, and she didn’t want that to happen to her or anyone else. The idea of dating also terrified her: What if she never got picked? What if the relationship didn’t work out? How would she deal with that gallows of rejection? I Kissed Dating Goodbye, with its admonitions against casual dating, gave her enormous relief: “I thought if I abided by these rules, God will bless me with the perfect man.”

But Ross started questioning I Kissed Dating Goodbye during her college years. Though she had hoped to find her life partner by graduation, she quickly realized she didn’t know how to express or reciprocate interest in a man, because for so long she had associated that with “emotional fornication.” Anytime she made prolonged eye contact, initiated a conversation, or smiled too much with a man, guilt shut her down. It took about 10 years, Ross said, before she was able to disentangle from those deeply ingrained thoughts. By then, she was 30 and still single.

Ross wasn’t alone in her confusion.

Jodi Breneman was 13 when her father put a purity ring on her finger and watched her make an abstinence vow in front of her church congregation. Breneman loved the ring—it was silver, bearing a cross and a heart—and she wore it with pride all the way through high school.

As Breneman struggled with the normal but uncomfortable, flitter-flutter emotions of her teenage years, I Kissed Dating Goodbye seemed to explain so clearly and persuasively everything she was feeling. She decided that if the book’s principles were the “highest level of purity and righteousness” one could reach, she would adhere to them 100 percent.

She made her convictions clear to friends, even posting on her Facebook profile, “Thanks for asking, but I don’t date.” When others praised her for setting an example of purity while her Christian friends were sleeping around, she thought, “Yup, I love Jesus so much, I would never do that. And He loves me because of that.” She felt sure God would reward her dedication with the perfect soulmate. Despite a genuine desire to please God, Breneman now realizes she was dealing with a pride issue.

She was a college freshman when she realized that her anti-dating rules were no longer cool. In fact, they now sounded downright silly and embarrassing. She tried to break away from those ideas, but they were so ingrained that they popped out instinctively: Whenever a guy asked her out, she felt terror, because in her mind the request was almost tantamount to a proposal. She was friendly with men, but didn’t know how to flirt back, so men who initially had crushes on her backed off.

Now 29, still single and dateless in a church full of singles, Breneman no longer wants to wait around. She tried online dating but stopped after three dates that unearthed too-raw anxieties inside her—learning curves she wishes she had experienced back in high school.

Deep down, Breneman still desires a fairy-tale-like courtship, where a nice Christian, virgin guy with a clean dating slate prayerfully picks her out from a crowd of women. When she sees other beautiful, godly, single women in their 30s and 40s who also don’t get asked out, she struggles not to lose hope, and really wishes she had never read that book.

IN 2016, ONE WOMAN tagged Joshua Harris in a tweet that said, “Your book was used against me like a weapon.” Harris responded on Twitter with an apology. Another self-identified “IKDG victim” tweeted back that she was “37, never married, and now infertile. Set bar too high cause of ur book. Many regrets!” Again, Harris apologized. He later invited readers to send stories about how I Kissed Dating Goodbye affected them. More than 500 people wrote letters to him, some thankful, some critical, some blistering.

Harris remembers kneeling in his parents’ living room as a 20-year-old and praying, “God, let me write a book that will change the world.” He was, in his own words, “religiously zealous, certain, and restlessly ambitious.” He was also the perfect face for the purity movement: the young, handsome, charismatic son of homeschooling celebrities Gregg and Sono Harris, a naturally gifted leader who as a 17-year-old had already carved a niche of his own, speaking at conferences and publishing a magazine called New Attitude for homeschoolers.

At the time, Harris was fresh out of his first serious relationship and frustrated at the loose morals of his generation. He wondered what a God-pleasing romantic relationship looked like beyond just “don’t have sex” and “date only Christians.” At age 21, Harris believed he had the answer: Don’t date until you’re ready for marriage, and when you’re ready, court with the intentionality for marriage. Dating, he wrote in I Kissed Dating Goodbye, is not sinful in itself but is “part of the problem” that encourages sin: lust, self-gratification, emotional manipulation, and spiritual distraction.

His book shook the world of conservative evangelicalism at the perfect time: As the consequences of the sexual revolution became dire, the demand for a Biblical alternative to modern dating was hot. With its catchy title and appealing cover, Harris’ book presented countercultural solutions that seemed simple and safe, romantic and radical.

Perhaps too simple and safe, Harris now says: “I was very young, very limited in my own experience, and I came up with very simple solutions, when life is very complex.”

After 11 years serving as a senior pastor in Maryland, Harris moved his family to Canada, where he began graduate school at Regent University in Vancouver, British Columbia. Now 42, no longer a church leader “with all the answers” but a student with questions, Harris has met fellow students who told him how his book had negatively affected their romantic life—or lack thereof.

One of them was Jessica Van Der Wyngaard, a 31-year-old Australian who was once an “evangelist” for I Kissed Dating Goodbye, waiting for her “man in shining armor” to find her until, one day, she realized she was 27, still single, and had never been on a date. Van Der Wyngaard and Harris are now partnering on a crowd-funded documentary film project called I Survived I Kissed Dating Goodbye, which will examine how the book has shaped Christian views on dating and marriage.

TWENTY-ONE YEARS AFTER I Kissed Dating Goodbye, what have its former advocates learned? For one thing, despite the book’s goal of saving its readers from relational heartache, many of them have concluded that pain-free relationships just aren’t possible.

Josh Latterell, for example, read the book while growing up in a Minnesota homeschooling community that believed dating was worldly. At age 23 he entered his first relationship and tried to do everything right: He asked his girlfriend’s father for permission to pursue her. He prayed and journaled about the relationship. He waited a long time before he held his girlfriend’s hand and dated her with marriage in mind.

“I took the relationship so seriously that in my mind it was almost pre-marriage,” he says. “I put so much pressure on myself, and on her too.” When they married, they did so without recognizing red flags that Latterell believes later became factors in their divorce.

Today Latterell is a 39-year-old church elder with an 8-year-old daughter he talks to every night on the phone. He no longer believes that having his heart in the right place is a guarantee of a pain-free, risk-free relationship: “To truly love, you have to be vulnerable and open up to the possibilities of being hurt.”

Donna Ross experienced her own relationship hurt and heartbreak after she abandoned her courtship rules and began dating in her early 30s. But she says she wouldn’t change any of it, because it taught her how to communicate with men and deal with heartbreak. Today she is married and has a 16-month-old daughter.

It’s not to say that some relationships haven’t benefited from the principles of I Kissed Dating Goodbye. Kenneth Ly believes he probably would never have married his wife if not for the book. As he looks back to his courtship with Katie, he says he may have taken some principles in I Kissed Dating Goodbye to the extreme, but he also worries that people will too quickly dismiss the good ideas in the book.

Now serving as a youth pastor, Ly still preaches the main points from I Kissed Dating Goodbye to the kids who come to him with relationship angst and woes. “Intimacy and commitment must go together,” he tells these teenagers: Don’t say “I love you” just because you’re feeling giddy. Don’t date six girls at a time saying you’re just “exploring.” Respect the person, be serious about how you pursue romance, seek wise counsel, strive to honor God.

Ly says that when people lose sight of the big picture—to love God, to love others—the book turns into a legalistic weapon.

Harris says his documentary project won’t undo the pain that the book has contributed to many readers, but he doesn’t want to repeat his previous mistake: He recognizes that life, people, and relationships are complicated, nuanced, and unique—and so their stories will be that way too, whether they loved or hated his book (see “Hindsight and hope” in this issue). This time, he says, he won’t offer a quick answer, but will simply listen. And maybe, out of those voices, people will find healing and grace—for themselves, and even for Harris.