AI Dating Apps Are Making You Worse at Love

How AI is killing authentic connection, one algorithm at a time

"They had exchanged messages for weeks, Wilson said. But who had he really been talking to?

‘It’s almost like we never even spoke.’”

This closing line from a Washington Post article about AI infiltrating dating apps stayed with me for weeks and thrust me into a quasi-existential dread for the future of the human race.

Richard Wilson thought he'd finally met someone interested in thoughtful conversation. They connected and bonded over weeks of dialogue. But when they met in person, his date had none of the conversational energy she'd shown over text. The article explores the growing prevalence of people using AI to craft romantic messages and handle entire courtships, optimizing our most intimate communications for algorithmic success.

Wilson's experience crystallizes what worries me most about AI infiltrating personal communication: What does this do to our ability to hold a conversation with another person? How can you reveal your true self and be authentic if you're constantly having AI coach, supplement, and wholly construct your thoughts?

The New Courtship

Apparently I’ve been living under a rock (or am just married - so not the target audience), but every major dating app has deployed AI to handle communication in some way. The features range from the innocuous - Grindr will summarize your chats so you can remember what you talked about.Bumble and Tinder propose enabling the app to swipe for you entirely (no bias concerns here!) The dating conglomerate Match has proposed to AI to scan messages before you send, asking “Are you sure?” It’s giving chaperone vibes, at scale.

Now, at this point, you may be pointing out to me - “Maria, they have ALWAYS had AI on these platforms - how do you think matching works?” Fair point.

But there’s a crucial difference - traditional dating app AI curates potential matches and put them on your screen. You, person, still have to choose and chat. Now?

Not anymore. These apps like Rizz will talk for you.

This Isn't New... Or Is It?

Why does this matter? So people are getting help to talk to each other. A common trope in literature is someone helping another person woo someone, often by feeding them lines, writing on their behalf, or talking through an earpiece. Variations of original Cyrano de Bergerac abound:

• Man loves woman but is insecure, believes she won't love him back

• Man communicates his love through a conventionally attractive conduit

• Woman falls in love with conduit because of the words

• Woman discovers the truth

• Woman falls in love with the insecure man

What do we learn from this pattern? We fall in love with the person helping the wooer in question - why? Their words enthrall, land. But, at the other end of this story is always a person, someone whose words moved hearts and minds.

When AI is on the other end, do you fall in love with the algorithm?

The answer to this reveals why AI assistance is more troubling than traditional help. It has to do with the type of communication we’re engaging in at all.

The Philosophy of Communication

Jürgen Habermas distinguished between two types of communication. One is strategic action, using communication to achieve your goals (efficiency, getting dates). The other is communicative action, genuine dialogue aimed at mutual understanding.

When people use AI to craft messages, they're engaging in strategic action - trying to "win" the dating game. But dating is supposed to be communicative action - two people genuinely trying to understand each other.

Like Habermas, Martin Buber divided human communication into two types. I-Thou communication is genuine, authentic, with no predetermined goal, both persons equal, not based on usefulness to each other. I-It is primarily concerned with achieving an outcome, with engagement largely one-sided.

We need both types of communication for a society to function. However, what’s worrying is that I-It outcome based communication is becoming the only type of communication that exists, and is shaping the way we engage with relationships in the world.

What do we lose?

AI-mediated dating is treating the other as the object. It replaces communicative action with strategic action - it's not helping you communicate authentically, it's optimizing for algorithmic success metrics (response rates, engagement, etc.).

As I said in my last piece - outsourcing our thinking to AI is a slippery slope. Like sports, learning a language, maintaining friendships - it takes effort and action on our parts.

Communication skills will atrophy. Like GPS making us worse at navigation, AI communication makes us worse at reading emotional cues, tolerating awkward silences, improvising responses, and being vulnerable in real life.

Expectation of creep. We start expecting all human communication to be as polished as AI-generated content. Natural human messiness becomes intolerable.

The "uncanny valley" of romance. When AI-assisted people meet IRL, there's a jarring disconnect between their digital eloquence and human awkwardness.

An aside: I get it - when I had Claude review this piece as my copy editor, it returned edits that to me sounded more polished, compelling, wittier than what I wrote. It sounded how I want to sound, without the hours of rereading, massaging, bending words and structure to my will. But, I get the uncanny valley feeling - it’s not me.

The beauty and humanity in struggling for words

There is a scene in A Nice Indian Boy where Naveen is trying to text guys, flirtatiously.

“Hi Jeremy, I was talking to my mom today, and I remembered - you have a mom.”

“Hey Rahul, umm, was drinking water today and thought of you because you said you need to drink more water. Ha ha ha.”

We struggle to communicate for a wide range of reasons - emotional limitations like shyness, fear of judgment; language issues like difficulty finding the word to express what you feel. But I think that you are meant to stumble over your words, have it on the tip of your tongue, be on the cusp. We’ve developed all these phrases for when we just can’t seem to find the word because this is fundamentally human.

I don’t think that we’re meant to be able to articulate perfectly at first because that shuts down conversation. Conversations are dialogues - back and forth reconciling of ideas. Wait, what do you mean by that? Oh, I see what you’re saying.

If you deliver something perfectly the first time, there is nowhere for the conversation to go. In Habermasian terms, stumbling is proof of genuine communicative action. It shows you're actually thinking, responding, being present with another person rather than executing a strategic program.

The authenticity paradox

In a world obsessed with the word, authenticity - being true to who you are - how can you be authentic if you outsource your thinking to something else?

Large language models are amazing pattern analyzers and predictors. When you ask AI to respond for you, it's generating the most statistically likely words based on millions of data points. But you are uniquely human. Only you can create thoughts unique to yourself.

And what are the second-order effects? When you actually meet the person, isn’t it scarier not being able to meet the expectations that you have set?

Wilson's story highlights what happens when we let AI handle our most human moments. He thought he was building genuine a connection, but he was really just talking to an algorithm optimized for engagement. When they met in person, the wit and warmth he'd fallen for vanished because it had never belonged to her.

This is the trade we're making: algorithmic efficiency for authentic connection. Every AI-crafted message means less practice being vulnerable, stumbling through our thoughts, learning to be present with another person.

We live in a physical world and need physical interactions. The stumble, the pause, the search for words, these aren't bugs in human communication, they're features. They're proof of genuine presence, authentic struggle to connect across the void between one consciousness and another.

When we let AI smooth away all the friction in our conversations, we risk losing the very thing that makes us human: our beautifully imperfect attempt to understand and be understood. Your imperfect attempt to find the right words isn't a problem to solve—it's proof you're actually human. And right now, that's the only thing algorithms can't replicate.