Is AI The Ultimate Dating Wingman Or A Romance Killer?

It starts with a blinking cursor and a blank text box: What do I say? For a growing number of singles, the answer isn’t a pep talk from a best friend, it’s a chatbot.

From polishing dating profiles to crafting flirty openers and even composing breakup messages, artificial intelligence is quietly reshaping modern romance. But as more people turn to algorithms for emotional assists, experts are divided on whether AI is helping love flourish or hollowing it out.

Celebrity matchmaker Susan Trombetti, CEO of Exclusive Matchmaking, says the appeal of an AI wingman, or wingwoman, is obvious, but limited. AI may be able to help open a door, but you still have to be the one walking through it.

“AI can help you get a date, but it can’t build the bond that makes a relationship. You can’t substitute the real thing’ when it comes to building a relationship,” she says. “Your personality always needs to shine through, which means it’s OK to use it to write something or say something in a better way, but it needs to come from you.”

Trombetti says AI “can open the door, but if it becomes your Cyrano de Bergerac then you are obviously going to fail and that’s not authentic or honest.” In the play “Cyrano de Bergerac” by Edmond Rostand, a fictionalized version of the real 17th-century novelist and playwright Cyrano de Bergerac feels he is too ugly to woo the woman he loves, and so writes love letters to help a young soldier woo her instead. It becomes so difficult for the soldier to pretend to be as eloquent as the letters suggest he is, that he ultimately decides he would rather be loved for who he really is.

“I had a client that used it to help him write love letters and poetry to his now wife, who wanted this level of romance. After a while, he stopped, though, and told her this wasn’t sustainable,” she says. “He felt it wasn’t authentic.”

Using a chatbot to flirt may boost confidence, Trombetti says, but “what’s going to happen when you meet in person?” Even worse? Letting AI handle the hard stuff. 

Breaking up with someone with an AI-written message “is cold and evasive, and downright disrespectful,” Trombetti says. “It’s taking the easy way out, which makes you a wimp with no character. It’s about avoiding the hard conversations, and that’s [what] makes you real and authentic even though it can be messy.”

Jeff Burningham, author of “The Last Book Written by a Human: Becoming Wise in the Age of AI,” sees nuance in the trend. Getting help drafting a message, he says, isn’t necessarily deceptive.

“If someone uses a chatbot to help craft a message because they’re nervous, that’s not inherently dishonest. Most of us have always asked a friend for advice and AI is just the new potential friend in the room,” he says. But he draws a clear line between assistance and avoidance.

“The deeper question is this: Are you using AI to express yourself more clearly, or to avoid facing and being yourself altogether?” Burningham says. “Flirting is sometimes awkward. Vulnerability is scary. That’s part of the magic. When you let a machine smooth all the edges, you may increase efficiency, but you risk decreasing authenticity. And intimacy can’t grow where authenticity is lacking.”

When it comes to breakups, Burningham is blunt: “To outsource that moment to a machine can feel less like kindness and more like emotional automation.”

“Breakups are painful because love is real. Heartbreak is part of the embodied human experience,” he says. Using AI to break up with someone “might soften the words, but it can also remove the humanity.”

Still, not everyone sees AI as a threat to romance. AI and consumer trend expert Matt Britton, author of “Generation AI,” says the technology can be empowering when used thoughtfully.

“For many, using AI to help break the ice or find the right words is empowering. It lowers the barriers to starting a conversation and can help people express themselves more confidently and authentically,” he says. “Even when it comes to difficult moments like breakups, AI can offer guidance on how to communicate with empathy and clarity — something that many people struggle with.”

Britton says intention matters. “The key is to use these tools as a springboard for genuine connection,” he says. “Rather than making things colder, these tools can actually help people approach sensitive conversations with more thoughtfulness.”

Ultimately, the debate may say less about technology and more about courage. AI can optimize a bio, suggest a clever reply, even outline a breakup script, but it can’t show up on a first date. It can’t feel nervous excitement, or risk rejection.

“In the age of AI, the temptation will be to optimize everything… including romance,” Burningham says. “But relationships aren’t meant to be optimized. They’re meant to be experienced. Messy. Real. Unscripted. And therefore beautiful.”

In an age obsessed with efficiency, romance may be one of the last things that resists optimization. The question isn’t whether AI can help you get a date, it’s whether you’re ready to be fully, imperfectly human, and love the imperfect humanity of another.

As Burningham puts it: “Love is still the answer. Even, and especially, in a digital world.”