Dear Anna,

I’ve been dating my boyfriend for about four months, and things have been going really well — or at least I thought they were. He’s always been really thoughtful over text, sending me these sweet, articulate messages about how he’s feeling or why he appreciates me. I’m not the most eloquent person, so I’ve always been a little impressed by how good he is at expressing himself. Last week, he sent me a long text about how much he was looking forward to our weekend plans, and at the top it said “Here’s a message you can send to your girlfriend.” My stomach dropped. I immediately realized he’d been using ChatGPT to write his texts to me, and he’d accidentally copied the prompt along with the message. When I confronted him about it, he was embarrassed but also defensive. He said he struggles with putting his feelings into words and just uses AI as a “tool” to help him communicate better, like using spell-check or grammar suggestions. He insisted the feelings are real, he just needs help articulating them. Part of me understands that not everyone is great at expressing themselves — because I’m not! — but another part of me feels hurt and confused. Were any of those sweet messages actually from him, or was I just falling for a chatbot? I don’t know if I’m overreacting or if this is actually a huge red flag about authenticity and emotional availability. — Texting With Emotional Robot/Person

Dear TWERP,

Oh man. This is such a perfect encapsulation of our times — where you can’t even trust that the person on the other end of the screen is actually the person on the other end of the screen.

Let me start by saying that your feelings of confusion and hurt are completely valid. You thought you were building intimacy with your boyfriend, and it turns out some of that intimacy may have been filtered through AI. Those messages felt meaningful because you believed they came from him — and now you’re suddenly questioning what was genuine, what was edited, what was entirely made up and how much effort he was actually putting in.

That uncertainty is the unsettling part.

That said, I don’t think this is automatically a deal-breaker, but it does require a real conversation about honesty, communication and what authenticity means to both of you.

Here’s where I have some sympathy for him: Not everyone is good with words. Some people genuinely struggle to translate their internal feelings into coherent sentences, especially over text, which is devoid of facial cues, tone, immediacy and nuance. If he’s using ChatGPT as a starting point to organize his thoughts — like “I feel X, Y and Z, help me say this better” — that’s closer to using a thesaurus than it is to outsourcing his entire personality. But if he’s typing “write a romantic good morning text to my girlfriend” and copy-pasting whatever comes out, that’s a different beast. One is assistance. The other is outsourcing emotional labor.

The real question is: How much of him is actually in these messages? Is AI polishing his communication, or generating it? Because those are two very different things. If he’s willing to show you part of his chat history, it might put you more at ease. (Or it might make things way worse, depending!)

And honestly, I empathize with why this rattled you. I have a friend who told me they use chatbots to soften difficult texts or help structure emotionally charged conversations, and I absolutely understand the appeal. Communication is hard. But then they texted me something that seemed suspiciously chatbot-ish and it gave me such pause. There’s a strange sci-fi feeling when you start wondering whether someone’s warmth, phrasing or vulnerability was crafted by a machine. It can make you question the intimacy itself.

Especially when our very notions of “reality” are shifting by the minute and we can no longer tell immediately what’s real and what’s not.

As my adorable mom-friend who is constitutionally incapable of swearing might say, What a mind fudge.

But back to you. Let’s remember that texting is a very small part of a romantic relationship. So how does he show up in person? Is he emotionally present face-to-face? Does he listen well, remember details, express affection and make you feel cared for when there’s no screen between you? Or are the texts carrying the emotional weight of the relationship?

Because if he’s warm and engaged in real life, this may genuinely be about insecurity around writing and self-expression. Plenty of people freeze up over text and use tools to help organize their thoughts. Awkwardly enough, he may have been trying harder than you realized to impress you and make you feel cared for, not less.

But if the texts are the only place he seemed emotionally articulate, then your discomfort makes a lot more sense. In that case, the AI may not just be helping him communicate — it may be compensating for emotional skills he doesn’t yet have. (And very much needs to work on.)

I also think his comparison to spell-check is a little too convenient. Spell-check fixes typos. AI can generate tone, vulnerability, romance, reassurance — the stuff that actually creates emotional intimacy. Those aren’t the same thing, and he should be willing to acknowledge the difference instead of brushing your discomfort aside.

So no, I don’t think you’re overreacting. But I also don’t think the solution is to panic and assume your boyfriend is secretly dating you by chatbot proxy. This is less a question of “Is AI evil?” and more a question of transparency. If he’d casually said early on, “Hey, I’m terrible at wording texts, so sometimes I use AI to help me phrase things,” this probably would’ve landed very differently than discovering it accidentally in the middle of what you thought was a heartfelt message.

I’d tell him that going forward, you want messages that be from him — even if they’re clumsy, imperfect or riddled with awkward typos. Most people would rather receive a sincere, autocorrect-turned-love-into-loaf text than a beautifully phrased one written by software.

Real intimacy lives in the imperfections anyway.

And if he absolutely insists there’s no meaningful difference between his words and AI-generated romance, then well, I’d be concerned. Because the issue stops being the technology and starts becoming his understanding of emotional honesty. Because, again, if he can’t express his feelings without AI assistance, then he needs to work on that skill, not outsource it.

Though if things go south, I will admit the temptation to use ChatGPT for the breakup text would be a kind of poetry.

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