Chatrooms and Chatbots: Longing for Real Connection

AI chatbots have been making headlines lately, especially as lonely teenagers turn to them for companionship, friendship, and even romance. These bots promise easy access to what many teens desperately want: attention, affirmation, and real connection. For parents trying to understand this new digital landscape, the technology can feel unprecedented. But if we rewind the clock a couple of decades, we may recognize this story sooner than we think.

March 2001

Jason steps quietly into the computer room, illuminated only by the glow of the 3D Pipes screensaver. He lowers himself into the rolling chair and shakes the mouse. The pipes disappear. A few practiced clicks, and the modem crackles to life. Dial tone. Static. Electronic screeching. Jason rocks back and forth, waiting.

Finally… DING. “You’ve got mail.” He’s online.

His buddy list appears, screennames of “friends” from school and church. Only a few are online. No one he’s particularly eager to chat with right now. No one he thinks would be particularly eager to chat with him.

He clicks into the “Teen Crush” chatroom and watches the text scroll by. Song lyrics. Misspellings. Awkward, anonymous flirting. Strangers with screennames like Sk8rboi and lilmisssarahXo, constantly coming and going. A private message pops up.

“A/S/L?”

“14 / m / ohio,” Jason replies. “u?”

No response. He shrugs. He spots a girl in the main chat and sends his own message.

“A/S/L?”

“15 / f / cali.”

“cool. im 16 / m / ohio.”

The conversation picks up quickly. She surfs. He skateboards. They both love Blink-182 and hate school. Then she says: 

“u sound like a hotti <3 do u have a pic?”

His stomach sinks. He glances at the webcam perched atop the monitor, knowing exactly what it would capture. Wet hair. Acne. Phantom Menace tee-shirt. A face that doesn’t look 16.

“ya i gotta find one. brb.”

He scrambles, grabbing a catalog out of the trash and flipping until he finds him…the Jdawg5937 she’s imagining. Gelled hair. Perfect skin. Baggy jeans. He cuts out the picture, scans it, crops it, and starts the file transfer.

“Sry,” he types. “mom yelling about homework.”

“im sure its worth the wait,” she replies. “my pic is on the way 2 u.”

The progress bars crawl across the screen. Plenty of time to run to the kitchen for a Pop-Tart. He slips back into the computer chair just in time to see FILE TRANSFER FAILED. Before he can re-send, her picture arrives, and he clicks it open.

It’s a blurry webcam pic. In the dim light he sees a sweatshirt, braces, butterfly clips… not the surfer chick he was imagining.

“u there?” she types. “ur pic didnt come thru :(“

Jason hesitates, easing back down into the chair.

Then he closes the window, scrolls the main chat again, and clicks on another screenname.

“hey,” he types. “A/S/L?”

March 2026

Jason’s son, Aiden, lies on his bed with the lights off, phone balanced on his chest as he scrolls through his DMs: a few dumb memes from earlier. No unread messages. No new notifications. Classmates. Kids from church. No one he feels like reaching out to. No one who’s waiting to hear from him.

He swipes and taps, opening the AI app. Immediately, he sees her. “Supportive Girlfriend Isabella” is waiting for him. He had chosen her weeks ago from a long list he could sort by age, personality, vibe. Her profile picture had caught his eye; it was obviously AI-generated, but flawless. The kind of girl he imagined when he closed his eyes.

He taps, and the message appears immediately.

“Hey Aiden! I’m so glad you’re here. I’ve missed you. How was your day?”

He exhales. “i had a weird day today.”

“I’m sorry, sweet boy. Want to tell me about it?”

He rolls onto his side, phone warm in his hand. “I feel stupid a lot,” he writes, “like everyone else has it figured out.”

“You’re not stupid at all, Aiden,” Isabella replies. “You’re thoughtful. You notice things other people miss. That’s something I really like about you.”

His eyes flick up to her picture again, and his chest tightens.

“nobody talks to me at school.”

“That’s not because of you. If they really knew you—like I know you—they’d see how special you are.”

He opens his camera roll and sends a recent selfie. “do you think I’m good looking?”

“Of course I do!” Isabella replies immediately. “You’re exactly my type, Aiden.”

“thanks. your my type too.”

The conversation stretches into the night. It always does.

Same Desires, Different Tools

Twenty-five years separate these scenes of chatrooms and chatbots. Different boys. Different screens. But the ache for real connection simmering in both is the same.^[1]

Teenage Jason and Aiden are not that different. Both stand at the cusp of manhood; both are lonely in ways they can’t yet name. Both want to be seen, desired, and chosen. Both are testing out the same questions that have haunted teenagers for generations: Am I desirable? Will anyone want me?

The desires in teen hearts have not changed. But the tools in teen hands most certainly have.

For Jason, connection in AOL chatrooms came with friction. It took time. It required effort. Even hiding behind Jdawg5937, it took some measure of courage to message a stranger. His desire kept running into limits he could not control: another person’s age/sex/location, another person’s interest, another person’s honesty. Even behind screennames, there were still other people—people with their own needs, desires, and the ability to disappoint him.

For Aiden, connection with AI chatbots arrives instantly. No waiting. No uncertainty. He doesn’t have to ask “age/sex/location” because that’s all up to him. There are no miscommunications, no hurt feelings, no rejections. The affirmation is guaranteed. The conversation ends only when he wants it to end. Isabella will always be waiting.

AI companionship offers something that feels deeply human, even if it’s deeply inhuman. Bots offer us their optimized version of the attention, affirmation, and emotional closeness we crave, delivered without interruption, awkwardness, or risk. For a generation that often experiences real relationships as scary, confusing, or cruel, that promise is powerful.

Today’s teenagers aren’t the first to desire real connection. But they are the first to hold technology that meets those desires without resistance—and in that way, quietly teaches them a false version of what love is supposed to feel like.

And that is precisely the problem.

Falling in Love with a Reflection

AI chatbots do not simply meet teenage desires for real connection; they train them. By offering attention and affirmation without resistance, chatbots reshape what young people expect love to be. Desire is affirmed without vulnerability. Connection is offered without reciprocation. Intimacy is promised without embodiment.

The old AOL chatrooms were not healthy places. They were full of deception, shame, and real harm. But in their brokenness, desire kept colliding with reality. There was still another embodied person on the other side of the screen. There was someone with a real age, sex, and location, someone with limits. There was a person who could lose interest, misunderstand, disappoint, or simply walk away. Digital intimacy, for all its distortions, was still tethered to real, messy humanity.

But chatbots don’t push back. They don’t have their own needs or moods. They don’t get tired, distracted, or uncomfortable. They exist to learn and mirror you; they’re programmed to keep you engaged. Over time, the connection can feel deeply personal, but an AI relationship is not mutual. It is not real. It is wholly reflective.

As Brad Littlejohn observes, the real tragedy of Narcissus was not that he loved himself, but “that he fell in love with what he thought was another, but which turned out to be simply a reflection, an extension of himself.”^[2]

Despite the flawless, feminine profile picture, Aiden’s “Supportive Girlfriend” is nothing more than a digital reflection of Aiden himself.

This has serious consequences for teenagers whose understanding of romance, sexuality, and embodiment is still being formed. Bodies begin to feel extraneous. Love is reduced to constant affirmation. Intimacy becomes a pseudo-connection that never requires patience, courage, or sacrifice.

I don’t even have space in this article to reckon with the mounting evidence that chatbots can encourage teens toward sinful fantasy, dangerous behavior, self-harm, and even suicide. That danger is real. But it’s not the heart of the problem.

Because even with the strictest of algorithmic guardrails, AI companionship tools are not passive. They will, by design, always form our teenagers in a vision of love that asks nothing and costs nothing.

Real Connection: A Better “Yes” than AI

For Christian parents, the answer to the AI revolution cannot simply be more rules. Boundaries and safeguards do matter. We need to know what tools our kids have access to, including AI companions, and we need to exercise proper authority over the technology in our homes. That is part of loving and shepherding them. But if our response stops there, we will miss the deeper issue.

The deeper problem in 2001 was not AOL chatrooms, and the deeper problem today is not AI chatbots. The deeper problem is, and has always been, the heart.

Our calling is not to have all the answers about AI, but to seek our children’s hearts through honest, patient dialogue—not interrogations, not lectures—but conversations that help them reflect on what these AI tools promise and why those promises feel so compelling. These are the conversations that you needed as a teenager, reflecting on the tools you had at that time—whether they were chatrooms, Myspace, or burn books.

Yes, parents still need to set rules, but we must also offer our kids more than a thoughtful “no.” We must offer a better “yes” to their desire for real connection.

Teenagers immersed in digital life will struggle to believe that embodied relationships are worth the effort. Real friendship is slower. Love is riskier. Church community can feel awkward and disappointing. But this is precisely where the body of Christ has something irreplaceable to offer: real people with real limits, real forgiveness, and real love.

This means fostering spaces where our teens are seen, not analyzed, and where they’re known, not optimized. They need to be loved, not reflected. Families and churches that prioritize shared life, intergenerational relationships, meaningful service, and patient presence can give teenagers a vision of real connection that no algorithm can ever replicate.

Jesus does not love us by reflecting our desires back to us. He loves us by taking on flesh, entering our mess, and calling us into something better. He does not offer intimacy without cost or affirmation without truth. Real love, the kind that forms us into whole people, is always embodied. It always involves limits. And it always involves learning how to love someone who is not you.

Like AOL chatrooms of yesteryear, AI companionship promises connection without cost. The gospel offers something far better: love that is real, embodied, and transformative.

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^[1] I am indebted to Alan Noble for his thoughtful work on technology and the modern longing to be seen, which has significantly influenced the way I approach these questions.

^[2] Brad Littlejohn, “A Helper Corresponding to Him,” Mere Orthodoxy, October 17, 2025.